The Pimp’s Assistant: Natasha Leggero

Summary

Podcast Summary: Disgraceful with Grace O’Malley - Episode: The Pimp’s Assistant: Natasha Leggero

Host: Grace O’Malley
Guest: Natasha Leggero
Release Date: March 27, 2025

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1. Introduction and Co-Host Audition

Timestamp: 01:25 – 02:18

Grace O’Malley welcomes Natasha Leggero to the podcast, expressing her nervousness and admiration for Natasha's work. Grace introduces the episode's unique format where she auditions potential co-hosts through a series of engaging and comedic interactions.

Notable Quotes:

• Grace (01:30): "I'm a nervous wreck. I am a very huge fan, and I'm trying to play it very, very cool."
• Natasha (02:04): "Why not?"

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2. Establishing Roles: Devil vs. Angel Dynamics

Timestamp: 02:39 – 03:35

Grace and Natasha discuss the classic devil-angel dynamic often present in partnerships. Grace probes which role Natasha envisions herself in if they were to co-host together, leading to playful banter about their personalities.

Notable Quotes:

• Grace (02:43): "Sometimes in two people's scenarios, there's a devil and an angel in a dynamic."
• Natasha (02:50): "Oh, I feel like you're definitely nicer than me."

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3. Parenting and Family Life

Timestamp: 04:26 – 09:03

The conversation shifts to parenting, with Grace sharing her recent trip to Disneyland for her sister’s birthday. Natasha elaborates on her experiences as a mother, highlighting her efforts to balance indulgence with cultivating good habits in her seven-year-old daughter.

Notable Quotes:

• Natasha (07:06): "But I froze my eggs because I was like, oh, who knows? Something could happen."
• Grace (08:07): "She doesn't have. She's, like, one of the only people I know who isn't addicted to a device."

---

4. Comedy Career and Experiences

Timestamp: 10:00 – 19:02

Natasha delves into her journey in comedy, recounting her early struggles and the pivotal moments that shaped her career. She shares anecdotes about bombing her first stand-up sets and the mentorship she received from comedian Bobby Lee, emphasizing the importance of perseverance in the industry.

Notable Quotes:

• Natasha (17:00): "I was like, that's the dumbest thing I've ever heard."
• Grace (10:06): "I'm a comedian."

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5. Personal Stories and Anecdotes

Timestamp: 19:02 – 28:52

Natasha narrates her tumultuous six-month stint in Australia, where she worked as a pimp’s assistant out of love for a con artist. She describes the chaotic experiences and eventual realization that led her back to the United States, using humor to reflect on the absurdity of her past decisions.

Notable Quotes:

• Natasha (17:35): "I fell in love with a con artist."
• Grace (19:02): "Wow. And it's good to learn early on for sure."

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6. Work-Life Balance and Relationships

Timestamp: 28:52 – 43:36

Grace and Natasha discuss the challenges of balancing a demanding career in comedy with maintaining romantic relationships. Natasha introduces her podcast, "The Endless Honeymoon Podcast," where she and her husband offer relationship advice, highlighting the dynamics of their partnership.

Notable Quotes:

• Natasha (47:50): "It's just better than couples therapy."
• Grace (43:36): "How do you balance it all?"

---

7. Comedy and Sensitive Topics

Timestamp: 43:36 – 55:18

The hosts touch upon the delicate nature of comedy, especially when addressing personal or sensitive issues. Natasha shares her experience dealing with a heckler who lost a brother to AIDS, illustrating the fine line comedians walk between humor and empathy.

Notable Quotes:

• Natasha (44:51): "And I was like, I'm sorry, man."
• Grace (45:04): "Do you recall the first time you were heckled negatively?"

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8. Jokes and Personal Insights

Timestamp: 55:18 – 67:29

In the “Jokes in My Notes” segment, Natasha reveals snippets of her comedic material and discusses her creative process. Grace commends Natasha’s unique delivery and her ability to infuse elegance into her humor, fostering a deeper appreciation for her comedic style.

Notable Quotes:

• Natasha (64:36): "I hate the Notes app because half of it is me trying to figure out how to stand up to this person who's harassing me."
• Grace (65:50): "I love that. That's a great angle right there."

---

9. Closing Remarks and Future Aspirations

Timestamp: 67:29 – End

Grace thanks Natasha for her time and contributions, reflecting on the insightful and humorous discussions. They briefly mention their respective projects, with Grace expressing enthusiasm for future collaborations and co-host possibilities.

Notable Quotes:

• Natasha (69:09): "Listen to our podcast, the Endless Honeymoon Podcast."
• Grace (70:15): "Thank you so much. I really appreciate it."

---

Conclusion

In this episode of Disgraceful with Grace O’Malley, host Grace engages Natasha Leggero in a lively and heartfelt conversation that traverses personal histories, the intricacies of parenting, the ebbs and flows of a comedy career, and the delicate balance of work and relationships. The episode is enriched with humor, candidness, and memorable exchanges, offering listeners both laughs and meaningful insights.

Full Transcript Highlights:

• Perimenopause Joke:

  • Natasha (65:47): "I wanted to do a joke about how, like, as you enter perimenopause, you kind of look around and you are very confused with your choices."

• Blind Date Anecdote:

  • Natasha (56:07): "I was dating again, an older man. I used to always date old dudes... It was awful."

• Comedy Bombing Experience:

  • Natasha (35:00): "I thought I was gonna... I bombed so bad."

These moments highlight the blend of humor and vulnerability that Disgraceful aims to deliver, making it a relatable and entertaining listen for comedians and general audiences alike.

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Notable Quotes with Timestamps:

• Grace (01:30): "I'm a nervous wreck. I am a very huge fan, and I'm trying to play it very, very cool."
• Natasha (02:04): "Why not?"
• Natasha (07:06): "But I froze my eggs because I was like, oh, who knows? Something could happen."
• Natasha (17:35): "I fell in love with a con artist."
• Natasha (44:51): "And I was like, I'm sorry, man."
• Natasha (64:36): "I hate the Notes app because half of it is me trying to figure out how to stand up to this person who's harassing me."

---

Recommended for Listeners Who Enjoy:

• Comedic conversations with a blend of personal anecdotes and professional insights.
• Behind-the-scenes looks into the lives of successful comedians.
• Humor intertwined with meaningful discussions on parenting and career challenges.

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For those who haven't listened yet, this episode offers a comprehensive peek into Natasha Leggero's life and comedic philosophy, all orchestrated through Grace O’Malley’s engaging hosting style. Tune in to witness the chemistry and laughter that define Disgraceful.

Transcript

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[Steve Buscemi]

Hi, this is Steve Buscemi. You know the actor. Well, now I'm an actor and podcast host. From Piece of Work Entertainment and Campside Media, in association with Olive Productions, comes Big Time, an Apple original podcast. Each episode follows the story of one misfit with big dreams who isn't afraid to bend a few rules or take a shortcut to get there.

[Grace O'Malley]

Well, who steals bees? I was duped.

[Natasha Leggero]

I shoot you in the leg.

[Steve Buscemi]

This is Big Time. Follow and listen on Apple Podcasts.

[Grace O'Malley]

Coming at you live from a shady Manhattan studio, it's Disgraceful, featuring your gracious ginger host. Hey, watch yourself. Only I can say that.

[Natasha Leggero]

Okay, boss, whatever you say.

[Grace O'Malley]

You pay my bills.

[Natasha Leggero]

Give it up for Grace O'Malley.

[Grace O'Malley]

All righty, Natasha, thank you so much for being here.

[Natasha Leggero]

It's great to be here.

[Grace O'Malley]

Thank you so much. And I'm gonna tell right now, I'm a nervous wreck. I am a very huge fan, and I'm trying to play it very, very cool. So it is. I'm super stoked to have you on.

[Natasha Leggero]

Well, you seem really cool and casual, and I think I like you.

[Grace O'Malley]

I'm. I'm nailing it.

[Natasha Leggero]

You. You really are.

[Grace O'Malley]

Okay, good. Cool. This is an. Listen. I'm learning, and we're. We're gonna get how we go. I think I'm gonna start off with a little segment that we have here on. On Disgraceful. It's. I used to have a podcast, and I. I had a co host, and now I'm looking for a new co host.

[Natasha Leggero]

Okay.

[Grace O'Malley]

And. And I'd like to ask you if you would be interested in being a new co host, and if I could ask you a couple of questions to see if we're a good fit.

[Natasha Leggero]

Why not?

[Grace O'Malley]

All right, let's do it.

[Natasha Leggero]

Actually, I don't know that I would have the bandwidth for this job, but I would definitely play along.

[Grace O'Malley]

Okay. All right, cool.

[Natasha Leggero]

And who knows, you know, maybe I could quit everything else.

[Grace O'Malley]

Yeah, I mean, you are a very, very busy, successful, you young woman, and you've got a very young. And a husband. Yes, of course.

[Natasha Leggero]

I'M incredibly young, and I have one child who's also very young.

[Grace O'Malley]

Seven years old. You guys are like twins, right? You're like, like Irish twins. You're eight, she's seven. Yeah, yeah.

[Natasha Leggero]

We're the same age. Okay. How can I be your co host?

[Grace O'Malley]

Sometimes in two people's scenarios, there's a devil and an angel in a dynamic. Which one did you think you'd be between the two of us?

[Natasha Leggero]

Oh, I feel like you're definitely nicer than me.

[Grace O'Malley]

Do you think so?

[Natasha Leggero]

Yeah.

[Grace O'Malley]

I could see it, but you don't. Listen, we don't know each other all that well, so I think we'd have to fight for that devil position.

[Natasha Leggero]

Oh, you want to be the devil?

[Grace O'Malley]

No. You can do that. I think you would play that actually a lot better now that I think about it fully.

[Natasha Leggero]

I tried to explain to my daughter that my. My casting is, like, evil. I'm like, I want to be like, evil, you know? And so, like, we'll be watching something and she's like, you're like this mom, right? Like Maleficent. And I'm like, yeah, How'd I know.

[Grace O'Malley]

You'Re going to say Maleficent?

[Natasha Leggero]

Well, she's seven. Yeah, that's what they, like, kind of hits.

[Steve Buscemi]

Hi, this is Steve Buscemi. You know, the actor. Well, now I'm an actor and podcast host. From Piece of Work Entertainment and Campside Media in association with Olive Productions, comes Big Time, an Apple original podcast. Each episode follows the story of one misfit with big dreams who isn't afraid to bend a few rules or take a shortcut to get there.

[Grace O'Malley]

Well, who steals bees? I was duped.

[Natasha Leggero]

I shoot you in the leg.

[Steve Buscemi]

This is big time. Follow and listen on Apple podcasts.

[Natasha Leggero]

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[Grace O'Malley]

We went to Disney yesterday for my sister's birthday. Disney adults are something else. Oh, where do you fall on that?

[Natasha Leggero]

Oh, I think it's hilarious. I think it's great that they go there and so much of their identity is built around this adult baby thing. Like, I don't. I mean, I Personally hate Disneyland. You know, they, they. Did you get your eye, your retinal scan?

[Grace O'Malley]

I don't think we did. I think I just willy nilly said, yeah, of course. That sounds like a great idea.

[Natasha Leggero]

Why is there a retinal sc?

[Grace O'Malley]

Because they work hand in hand with the tsa, I think.

[Natasha Leggero]

Oh really?

[Grace O'Malley]

I don't know. Cuz that tsa they skin in your eyes now too.

[Natasha Leggero]

I'm just like floored. And we have friends who go there like three times a year with their children. And the girl I was with, she's an adult and she was like, isn't the castle beautiful?

[Grace O'Malley]

I'm like a little small for my liking.

[Natasha Leggero]

Yeah. Like no, I've seen an actual beautiful house. Like I don't think that Disney castle is beautiful.

[Grace O'Malley]

I think it's a prop. And why are we glorifying the monarchy?

[Natasha Leggero]

Exactly.

[Grace O'Malley]

I did see it was. I think they have what you would call mental illness because I did see someone, they had like a light show last night and somebody did start bawling their eyes out when it started.

[Natasha Leggero]

So that is bizarre.

[Grace O'Malley]

Yeah, like a 40 year old man.

[Natasha Leggero]

He was crying because of the laser show at Disneyland.

[Grace O'Malley]

It was a tough watch. It was a tough watch for sure. I don't know.

[Natasha Leggero]

Well, you're the one who went there for her birthday.

[Grace O'Malley]

She had never been here before. So this is our when in Rome kind of thing. We had to take her.

[Natasha Leggero]

I tell my husband he has to take her. I'm not doing it. My husband was so into taking my daughter Disneyland. He wanted her to be able to ride all these rides and she wasn't tall enough. So he, he ordered her like Skechers, like high heels like, or not high heels, but like 2 inch platforms.

[Grace O'Malley]

I love, I love that. Because not only are you, are you taking a risk on your child's life, but you're also trying to make their best day the best. I guess so you might, you might have lost your daughter, but at least she was having a blast on a coaster.

[Natasha Leggero]

Well, if I was single parenting, I would definitely. She would not know about Disneyland.

[Grace O'Malley]

Yeah, you'd have to, you'd have to keep that a big secret.

[Natasha Leggero]

I would, yeah. She doesn't know about Legoland. I told my husband. You do not tell her about that.

[Grace O'Malley]

That's. I think that's a fair compromise because.

[Natasha Leggero]

That sounds like hell not going to Legoland.

[Grace O'Malley]

And imagine like you're trying to spend like a day off with your kid and you just keep stepping on Legos. It's like purgatory.

[Natasha Leggero]

That Is the life of a mother, Grace.

[Grace O'Malley]

Oh, wow. I. I'm looking forward to it. I am. Did you always want to be a mom?

[Natasha Leggero]

No.

[Grace O'Malley]

No. Do you have one of those bastard children or. You did it the right way.

[Natasha Leggero]

Well, I did it the way that a lot of people do it. In a doctor's office in Culver City. I, you know, I froze my eggs.

[Grace O'Malley]

Oh, yeah. Yeah. Okay.

[Natasha Leggero]

But I froze my eggs because I was like, oh, who knows? Something could happen.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

You have to freeze them by the time you're 38. That's what the doctors say. That's when you should really be, like, getting serious about checking the levels. And then I met my husband, and I was like, oh, this guy would be a really good dad, because I was, you know, raised by a single mom, so that doesn't really make you want to have a kid.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

But then when I met him, and he was so into it. But anyway, I'm so glad I did. And I'm trying to not urge everyone I know to have a child, but it's pretty amazing and makes everything else seem pretty stupid.

[Grace O'Malley]

Do you believe in the idea that, like, once you have your sweet baby girl, that it changes you for the better?

[Natasha Leggero]

Well, your values certainly shift, and it makes it really hard to, you know, you just want to be around them because they're these, like, cute little angels who don't know who Trump is. She doesn't have. She's, like, one of the only people I know who isn't addicted to a device.

[Grace O'Malley]

Oh, that's huge, too.

[Natasha Leggero]

And you just have these little, like, earthling magical beings, and they don't. I mean, it's coming.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

But the more I can slow it down in terms of, like, technology. Technology and just having her disappear into being forever elsewhere like everybody else.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

So it's. It's just special, I think.

[Grace O'Malley]

I think that's a beautiful thing to try to keep them away from technology as soon as you can.

[Natasha Leggero]

Well, I have her at this, like, school, and I realized that the. Because it's like a private school, kind of like a Waldorf based school. Do you know about that?

[Grace O'Malley]

No.

[Natasha Leggero]

It's very, like, the curriculum is very trad wife. Okay. They learn gardening, they learn cooking.

[Grace O'Malley]

They learn to stay in the kitchen as a young lady.

[Natasha Leggero]

They learn calligraphy to, like, write thank you letters.

[Grace O'Malley]

That's a lost art. And it's not even an art. It's just something that people should know.

[Natasha Leggero]

They learn woodwinds. It's. It's very. You know, they're planting seeds and like.

[Grace O'Malley]

When you're that young, these are like really great things. Like, rather than just like, that block is red, you know, like you're learning, like, life.

[Natasha Leggero]

Well, that's more like grace.

[Grace O'Malley]

But for me, I stayed back quite a few years. I. I had what they called troubles.

[Natasha Leggero]

Did you?

[Grace O'Malley]

No. But I feel like I could have benefited if I did.

[Natasha Leggero]

I feel like you were really loved by your parents. I'm feeling this from you 100%.

[Grace O'Malley]

I was the first child I actually was talking about yesterday at Disneyland. I had so much love. And also at the same time, maybe too much. Cause I had too much confidence. Like, I radiated confidence. And thank God for bullying. Knock me down.

[Natasha Leggero]

You were bullied?

[Grace O'Malley]

Yeah, of course. But thank God, because I would have. I would have been that person that you can't stand that's just like too confident, you know? You ever meet somebody who's too confident? It's like that person should really probably knock it down a few notches. Yeah, no, of course. Yeah.

[Natasha Leggero]

I'm a comedian.

[Grace O'Malley]

Yeah. Yeah.

[Natasha Leggero]

But, you know, it's usually fake. It's usually people are like, yeah, making up for something.

[Grace O'Malley]

No, I was like, you know what it took? It took. My mom signed me up for a drama club after school and she came to the rehearsal and as it turned out, it was actually a special needs drama club.

[Natasha Leggero]

Stop it.

[Grace O'Malley]

Knocked me down a few blocks. Yeah, that was good too. On top of the bullying, I liked it a lot.

[Natasha Leggero]

You were the one person without special needs.

[Grace O'Malley]

I was a goddamn star.

[Natasha Leggero]

You're like the Angelina Jolie.

[Grace O'Malley]

I was like, mom, you have to come see this. I am. I am the best. It is so good. I'm going to be on Broadway. And she came and saw. She said, sorry, you're never going back there again. And then later to find out it was for special needs kids.

[Natasha Leggero]

Wow. So what age did you start being bullied?

[Grace O'Malley]

That's about middle school. You think you're the only one with tits and you think that'd be a good thing. But for some reason they saw it as a bad thing. I don't know.

[Natasha Leggero]

You were bullied because of your tits. That does not count.

[Grace O'Malley]

It was. Well, it was. It was the. That's where it started. It was. The teachers started to bully me. They said I couldn't wear bead cut shirts to school and that. Really? Yeah. And I got kicked out of student council for that. Then I had, like, nowhere to go.

[Natasha Leggero]

So I had pre body shaming.

[Grace O'Malley]

Oh, yeah. 1,000%. Yeah. It would have been on the local news if it were now child with two breastesses kicked out of student council. But I don't know. Like, one of the girls, I. I was the only one who showed up to her birthday party. I don't know if she ended up swinging on me in between classes. I don't. It was physical. It was. It was fun. I learned to like it, though.

[Natasha Leggero]

You got beat up?

[Grace O'Malley]

Yeah. Yeah, I've been jumped a couple times. Have you ever been in a fight?

[Natasha Leggero]

I was in a fight in middle school.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

I got books thrown at my head.

[Grace O'Malley]

Oh, rats.

[Natasha Leggero]

And. Yeah.

[Grace O'Malley]

How did that. How that unfold?

[Natasha Leggero]

Well, this girl, they just. People just thought I was annoying.

[Grace O'Malley]

Yeah. You can't pinpoint it, right?

[Natasha Leggero]

Yeah, it's hard.

[Grace O'Malley]

Yeah. You're just annoying. One girl jumped me another time on Crazy Hat Day. And when she was all done, I didn't fight back. I wanted to go to private school, but I didn't know we couldn't afford it. And when she was all done, I said, well, why did you do that? She was like, I don't like you. I was like, oh, that's fair, I suppose.

[Natasha Leggero]

I mean, I remember this girl told me they used to make fun of me because I would wear these, like, John Fluvag shoes. I mean, not. Not unlike what I'm wearing now. Like, big, black, chunky shoes. And this girl would throw books at my head. And finally, like, her mom came, my mom came. We all sat down in the principal's office, and I said. I stood up and I said, I just want to be able to go to. Without having books thrown at my head and be able to wear the shoes I want to wear. And the girl's mom goes, well, your shoes are ugly.

[Grace O'Malley]

Oh, apple and the tree. It's really. It doesn't go far. That's crazy.

[Natasha Leggero]

Yeah.

[Grace O'Malley]

So was your mom. So your mom was a single mom. Did she have a few words with that mother or. No, we play nice.

[Natasha Leggero]

We were scared of her.

[Grace O'Malley]

Okay. Yeah.

[Natasha Leggero]

And then. And the daughter was pregnant. Oh, and then.

[Grace O'Malley]

You can't throw books back.

[Natasha Leggero]

No, exactly. That was, like, one of the reasons why I didn't. And then the funniest part was when my mom was leaving the school, we were walking down the. Like, the hallway, and the girl said to my mom, what are you looking at, bitch?

[Grace O'Malley]

Oh. Oh, I know. I know. Just the type. Yeah.

[Natasha Leggero]

And my mom was so scared.

[Grace O'Malley]

Yeah. That's petrifying a child. Impregnated person is yelling, what are you looking at, bitch?

[Natasha Leggero]

Yes. To my mother.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

That's why my daughter's in private school.

[Grace O'Malley]

That's why she. She's being one with nature.

[Natasha Leggero]

I know, but it's so hard because you really, you know, as a mom, as a parent, you want so much to over correct.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

All the terrible things that happen to you. But at the same time, like, I'm happy with my life, and I feel like my life is really great and I'm successful, and it's like, maybe that wouldn't have happened if I wouldn't have had to, you know, stick up for myself, feel scrappy.

[Grace O'Malley]

Yeah. I. I do think I've heard before, and this is somebody I know that went to college, had told me this. That was it. You, Nora. Somebody told me that you try to reverse the cycle that you're in so much that you. You make a new cycle. And, like, it's like you. You try to over correct, and then the cycle just keeps on going really hard.

[Natasha Leggero]

I'm trying to correct the cycle I have right now, which is saying yes to my child all the time and not making her do things she doesn't want to do because I don't want her to ever experience pain.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

Because it makes me so sad when she's upset. And, you know, it's. It's so easy to just kind of fawn over your child. And having an only child, like, I'll be brushing her hair and my husband will be putting on her shoes, and she can. She can do all these things herself.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

You know, and it's just really. It's a. We all have our own challenges, and.

[Grace O'Malley]

Nobody tells you how to parent. It's tricky.

[Natasha Leggero]

I mean, I want to give her sushi every night and. But see, that's the thing, too. That's another thing. I've given her so much great food to try to expand her palette.

[Grace O'Malley]

Oh, yeah.

[Natasha Leggero]

Because I'm from the Midwest, and I ate beefaroni until I was 39. Like, no one ever gave me anything. So I've given her so much stuff that, like, every teacher is like, she won't eat lunch. What kind of foods does she like? And I'm like, well, she, like, likes really nice restaurant food.

[Grace O'Malley]

She's into the finer things. Don't you have a chef? This is private.

[Natasha Leggero]

I thought, yeah, she likes quail eggs, and she likes caviar, and, oh, my God, it is like, it's a challenge, you know? And. And she's, like, already sick of sushi. Like, I never even had sushi.

[Grace O'Malley]

You know, it's like, you. You go home, like, beefaroni again. She's like omakase again.

[Natasha Leggero]

That's funny.

[Grace O'Malley]

She's just, you know, a little different. That's funny.

[Natasha Leggero]

Are you still interviewing me to be your sidekick? Did I get the part?

[Grace O'Malley]

Oh, that's an absolute. I've got a few more questions here. So would you say your on air personality is the same as your off air personality?

[Natasha Leggero]

I would say off air, I'm probably even more chill. I'm not gonna, like, work to insert myself.

[Grace O'Malley]

Yeah, absolutely. I think that's a good way to be. Did. Have you always been like that?

[Natasha Leggero]

No, I think when I moved to Los Angeles, I was very desperate. You know, I had come from New York.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

Well, by way of Illinois.

[Grace O'Malley]

Did you do Chicago?

[Natasha Leggero]

No.

[Grace O'Malley]

No. You just went right to New York?

[Natasha Leggero]

I went right to New York. Big, big failure there.

[Grace O'Malley]

How long were you in New York?

[Natasha Leggero]

Five years.

[Grace O'Malley]

Okay.

[Natasha Leggero]

Well, I went to school. I went to Stella Adler Conservatory and I got a degree in theater criticism from Hunter College.

[Grace O'Malley]

Oh, wow.

[Natasha Leggero]

And, yeah, so everybody's a critic. I mean, it's kind of cool, though, because it actually really trained my mind for comedy.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

Because comedy is just critiquing really well, at least the kind of comedy I do.

[Grace O'Malley]

Absolutely. Yeah. I mean, if you don't want to ever get better, then you don't critique, so you're right. Yeah. And that's. Those are the people who don't really particularly make it, I'd say. Do you.

[Natasha Leggero]

Oh, but I'm okay with you being in the spotlight. Is that what you're getting at? Am I going to step on your.

[Grace O'Malley]

Oh, no, I'm not like that. No, I would really like. I just want to. I'm trying to get to know you really, truly. Yeah. Here's a good one. If I were to run a background check, would I find anything juicy?

[Natasha Leggero]

No, unfortunately. Oh, wait, hold on. Yes. No, I did work in a brothel in Australia, but I answered phones.

[Grace O'Malley]

Okay, all right. Scheduling and all that.

[Natasha Leggero]

Scheduling. Cleaning towels. That was really disgusting.

[Grace O'Malley]

Okay, so a pimps assistant.

[Natasha Leggero]

I was kind of pimps. I mean, I did not last long, but I was in Australia and it was. It was the only job that had. It was like the highest hourly rate.

[Grace O'Malley]

Wow. That's. What. So how long were you in Australia?

[Natasha Leggero]

Six months.

[Grace O'Malley]

Six months. And you were. Did you.

[Natasha Leggero]

It was for love.

[Grace O'Malley]

For love?

[Natasha Leggero]

I fell in love with a con artist.

[Grace O'Malley]

Oh, wow. I feel like that's always like a pivotal point in a woman's life.

[Natasha Leggero]

It really is. And honestly, it happened when I was 23 and it was like, maybe like my first big heartbreak. But it made me so happy that it happened the way it did. Because how many people does that happen to when they're like 40 and then it's like, it's over. I don't know. It's like you've had a kid with them. Like, I just felt like I was so young to be experiencing this. And obviously it was very intense at the time. But, you know, I'm just glad because then I never fell for someone. I mean, he literally, like, would shoplift potatoes. Like, I would be like, you have like. He was a very small time con artist.

[Grace O'Malley]

It's like petty theft.

[Natasha Leggero]

Yeah, it was like petty theft. Or like, we would be like at a restaurant in Australia. And then he'd be like, okay, let's go. And I'd be like, we have not paid.

[Grace O'Malley]

Oh, no.

[Natasha Leggero]

And he's like, we're leaving. Wiener. He would call me wiener.

[Grace O'Malley]

Wiener. Well, because that's a term of endearment.

[Natasha Leggero]

It was. But also he was old. He was like, well, this is old to me now. He was 43, but I was like 23 at the time.

[Grace O'Malley]

Oh, yeah. No, he pictured the older things old.

[Natasha Leggero]

And it was just awful. But it was definitely a journey.

[Grace O'Malley]

Wow. And it's good to learn early on for sure. 100. Did you ever fall for anyone of the criminal aspect after that?

[Natasha Leggero]

No. It made me so cynical.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

You know, because it was. I couldn't believe that was happening. And then, I mean, the way it went down was so terrible because I just remember I'd had. I went there under the guise of like a student exchange because I was going to Illinois State University. That was before I got to New York.

[Grace O'Malley]

Gotcha.

[Natasha Leggero]

And so I was like, let me get out of here. So I had all this money from the school to go to Australia for like an exchange program. And then one day I was at the guy's house and the doorbell rings and he's like, wiener, I need you to put all that cash in. In the mailbox right now.

[Grace O'Malley]

And you're 20. They're like, this is like a movie.

[Natasha Leggero]

I know. And I was like, I went downstairs and he was getting beat up by some dude and they took his Rolex and I. And then afterwards. And I gave them all my money. It was. It wasn't that. It was like twelve hundred dollars, but it was like, it was all your money. It was all my money. And then afterwards I was like, why? Why did I have to give you this money? And he basically got this other girl pregnant. And he's like, Lucy is a crazy liar, and her brother just took my Rolex and I. I mean, I just believed dead Lucy never existed.

[Grace O'Malley]

He was in a mob.

[Natasha Leggero]

She did. But, like, he. Yeah. I don't know where. All my money just went to her, I guess. To her abortion. That's what it was.

[Grace O'Malley]

Oh, she's getting abortion.

[Natasha Leggero]

It was a long time ago. I forgot the details.

[Grace O'Malley]

I guess it was a good thing after all. It depends how you look at it, right?

[Natasha Leggero]

So. So that's like the.

[Grace O'Malley]

Lucy's life would have been hell without you. It sounds like. Oh, my God.

[Natasha Leggero]

I saved Lucy from having a baby with that guy.

[Grace O'Malley]

Truly and honestly, if you ever look at it like that, I never even thought of that. I like the happy outlook of it all.

[Natasha Leggero]

Yeah.

[Grace O'Malley]

Oh, wow. Yeah.

[Natasha Leggero]

So you might find something like that, but no, I've never been arrested or anything.

[Grace O'Malley]

Well, that is. That. That's even better.

[Natasha Leggero]

Have you.

[Grace O'Malley]

I fake id.

[Natasha Leggero]

Oh, I had a fake id, but I never got caught.

[Grace O'Malley]

Oh, that's good.

[Natasha Leggero]

What was it? It was. It was Minerva Santiago.

[Grace O'Malley]

That is. That's worse than the one they have on Superbad. That is terrible.

[Natasha Leggero]

And I didn't get caught, I guess.

[Grace O'Malley]

Because people were, like, ashamed to try pronounce it, maybe.

[Natasha Leggero]

What. What the situation was. I actually feel like if I had a superpower, it's getting into bars and clubs. Like, I was always able to do that my whole life. Get to the front of the line.

[Grace O'Malley]

Oh, yeah. You just. You walk in with confidence, but it.

[Natasha Leggero]

Doesn'T extend beyond that.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

You know, it's just like the.

[Grace O'Malley]

Yeah, like a niche time in life where you could get, like, nightclub, bar, and what else would you try to sneak into?

[Natasha Leggero]

A few operas. Like, when I was in Europe. Oh, that's because I'm sure, you know, I'm so small that, like, if I want. If I didn't have the money to see it, I just kind of, like, slipped in.

[Grace O'Malley]

Oh, that's awesome.

[Natasha Leggero]

Yeah, I've done that.

[Grace O'Malley]

And so how much time did you spend in Europe?

[Natasha Leggero]

Oh, I've spent many, many of time. Many of times.

[Grace O'Malley]

You sound like your daughter.

[Natasha Leggero]

And.

[Grace O'Malley]

Like, oh, Europe, Europe.

[Natasha Leggero]

Well, you know what's funny is I took her to Paris, and she keeps asking to go back, and she's like, I want to go back to that hotel we stayed at. And she's like, is it going to be as good as that? That had the little. The little cookies, and it was basically Versailles, and that is where she wants to go because they have, like, this little hotel that's like Where I guess the Minister of finance used to.

[Grace O'Malley]

Oh, yes, the Minister of Finance. I don't even know what that means. Well, it's.

[Natasha Leggero]

It's in Versailles. It's like a. You can actually spend the night at Marie Antoinette's, like, on her property, and then you get access to, like, a golf cart. But I did it for one night.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

And my daughter has not stopped talking about it.

[Grace O'Malley]

The standard is set, but.

[Natasha Leggero]

Yeah, the standard set. And so now she's just kind of like, we'll go to a regular hotel. And she's just kind of like, oh, fish posh.

[Grace O'Malley]

Yeah. I picture your daughter as Eloise.

[Natasha Leggero]

That is so funny, because she is part that, but she's also part, like, country, you know, future trad wife, you know?

[Grace O'Malley]

Oh, yeah, no, she. She's. Now she's Hannah Montana.

[Natasha Leggero]

Yeah.

[Grace O'Malley]

She's Miley Cyrus and Hannah Montana. She. She gets the best of both worlds.

[Natasha Leggero]

That is so funny. That is kind of what she is. Speak. She does. She also really wants to be a pop star, so I have played her a lot of. I kind of like Miley.

[Grace O'Malley]

I love Miley. Miley rocks. She could do no wrong in my eyes.

[Natasha Leggero]

Yes.

[Grace O'Malley]

Yeah. I'm a big Miley fan.

[Natasha Leggero]

And I was. I was playing my daughter. Like, she's really into being a pop star, so I was, like, trying to play her different people. And then I was playing her Stevie Nicks, and I was like, yeah. You know, a lot of people try to imitate her and my daughter, Stevie Nicks, and she's like, mom, I don't think she's that good, but I see a lot why she thinks that. Because it's not like a modern sound.

[Grace O'Malley]

Yeah, no, yeah.

[Natasha Leggero]

Now they just do a different sound.

[Grace O'Malley]

I'm curious to see what she thinks in 10 years.

[Natasha Leggero]

Exactly.

[Grace O'Malley]

I think when. When you're 17, you find Stevie Nicks and you're like, oh, she had it. She had it going on. That's when you start to realize probably.

[Natasha Leggero]

She was a little too young for that.

[Grace O'Malley]

What's her. What's her fave right now? Oh, you know, who shall not be named. Yes. Okay.

[Natasha Leggero]

The only thing she wants.

[Grace O'Malley]

Of course. It's all anyone wants. All the time. At every hour of the day she's.

[Natasha Leggero]

Asked for, she goes, mom, do you think maybe she doesn't know about I. You know, iPads or any. Or she knows about iPads, but she doesn't have one.

[Grace O'Malley]

Yeah, yeah.

[Natasha Leggero]

She's like, mom, do you think there's, like, something that you could get me that I could Just play some music on.

[Grace O'Malley]

Oh, my God. You know, I've got the perfect thing for you. This is called a Walkman.

[Natasha Leggero]

Well, I actually. So I went on ebay and got her, like, a 2021 iPod.

[Grace O'Malley]

Oh, perfect. They're still cooking those out.

[Natasha Leggero]

Well, you can buy it, like, used one. Like, they definitely stopped making.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

And, like, I think 2023, they stopped making them. I think a Nano or something.

[Grace O'Malley]

Oh, the rocks. Those are my favorite.

[Natasha Leggero]

I know. It is kind of nice because, like, who wouldn't want something? It's like, that doesn't have, like, multiple distractions built into it because I want something for her where she can just like, pick the song she wants and play it.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

And I think there's, like, a 2023 iPod that actually is Bluetooth too, so you don't have to have, like, the cord.

[Grace O'Malley]

That's huge. I think. I think those will come back around. They should, because I think people are looking to stop doom scrolling, obviously.

[Natasha Leggero]

I mean, I cannot look at my phone without an hilarious announcement.

[Grace O'Malley]

Oh, my God.

[Natasha Leggero]

It's always something like, why would you not want that?

[Grace O'Malley]

You know, I feel like I just, like, all day, every day, I'm just like, are we for real with this? And it's. But I'm also tuned in, and I can't look away, so.

[Natasha Leggero]

Well, you're young.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

It's like you're used to it.

[Grace O'Malley]

Yeah, absolutely. I do remember a time I was talking about this recently of when my mom got Facebook, and that's when she stopped paying attention to me. Yeah. But, like, not, like. Not, like, fully.

[Natasha Leggero]

That is horrible.

[Grace O'Malley]

Not fully stopping. Like, she always, like, would pay attention, but I didn't get, like, her at all hours of the day. They would be like, Facebook time. And I'd be like, hello, Facebook time.

[Natasha Leggero]

I hate what your mom said. It's Facebook time.

[Grace O'Malley]

No, but, like, in my head, I was like, oh, she's on Facebook. And this is. This is where she can't multitask right now.

[Natasha Leggero]

But she would probably be looking at it on a computer, right?

[Grace O'Malley]

She was. She was on a laptop.

[Natasha Leggero]

And so didn't you just kind of think she was doing her work?

[Grace O'Malley]

Just bartender. So I was like, you just care more about the people you went to high school with than you do about me. What the hell is going on?

[Natasha Leggero]

Well, Facebook's its own thing. I've never been into Facebook.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

I mean, I don't know what, like, my husband still is, like, getting updates on everyone he went to middle school with.

[Grace O'Malley]

They can be fun because Especially, like, wouldn't you like to check in on Ms. Book Thrower, see what she's up to? I'm sure things aren't all that great.

[Natasha Leggero]

Yeah. But do I need to donate to, you know, whoever's, like, doing a GoFundMe for their home birth? I mean, it's like, always something dramatic.

[Grace O'Malley]

You can just quietly scroll, and then.

[Natasha Leggero]

Don'T they know if you read it or.

[Grace O'Malley]

No, that's the best part.

[Natasha Leggero]

That's kind of cool.

[Grace O'Malley]

Yeah. Just don't like anything.

[Natasha Leggero]

Oh, right, right, right. Yeah.

[Grace O'Malley]

If anything, it's a. If you're. If you're feeling down. Facebook is a good scroll.

[Natasha Leggero]

I see.

[Grace O'Malley]

You'll feel better about yourself.

[Natasha Leggero]

But then, isn't it, like, your aunts all mixed into it, too?

[Grace O'Malley]

Yeah, I feel like they're just talk texting the. The good word of either the Lord or Trump. And so that's where I stay away.

[Natasha Leggero]

I see. Right. Because it's not so much about your algorithm as much as it is, like, who have you been in contact with your whole life?

[Grace O'Malley]

Exactly. Yeah. So it is kind of like, ah, it's a little scary.

[Natasha Leggero]

Right. Right. Oh, that. But that is a better scroll.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

See what the people like.

[Grace O'Malley]

Jesus Christ. Everyone I've ever loved and known is out of their minds.

[Natasha Leggero]

Well, you know, there's been mass insanity before.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

So might be coming back.

[Grace O'Malley]

We are. We're back, baby. We are back.

[Venmo Advertisement]

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[Steve Buscemi]

Hi, this is Steve Buscemi. You know, the actor. Well, now I'm an actor and podcast host from Piece of Work Entertainment and Campside Media, in association with Olive Productions, comes Big Time, an Apple original podcast. Each episode follows the story of one misfit with big dreams who isn't afraid to bend a few rules or take a shortcut to get there.

[Grace O'Malley]

Well, who steals bees? I was duped.

[Natasha Leggero]

I shoot you in the leg.

[Steve Buscemi]

This is Big Time. Follow and listen on Apple Podcasts.

[Grace O'Malley]

All right, we got this next segment. It's called in the Green Room. The idea of the segment is basically get to know you a little better. It's like if we were In a green room, hanging after a show.

[Natasha Leggero]

Okay.

[Grace O'Malley]

Kind of thing.

[Natasha Leggero]

Okay.

[Grace O'Malley]

I just wanted to ask if you have anything on your rider, and how has it changed over the years?

[Natasha Leggero]

You know, it's funny. I have a rider and I put caviar for two.

[Grace O'Malley]

Love that.

[Natasha Leggero]

No one ever, ever did it, really.

[Grace O'Malley]

Ever.

[Natasha Leggero]

Never once. No, never. Just sparkling water and fruit, which I didn't ask for, but.

[Grace O'Malley]

Oh, caviar. What's a good substitution? I don't know. Give her sparkling water and fruit.

[Natasha Leggero]

I've literally worked with comedians, though. I'll tell you who afterwards, who would just, like, take everything and put it in their purse, including the honey, all the pens, everything from the club. And they're like, no, this is like my grocery shopping.

[Grace O'Malley]

Whitney Cummings just came on and said she used to do that.

[Natasha Leggero]

It was her.

[Grace O'Malley]

Yeah. She was like, dude, I can't afford anything. I. I'm just gonna.

[Natasha Leggero]

At all. She can't afford anything.

[Grace O'Malley]

She said at the time she couldn't. That's hilarious.

[Natasha Leggero]

She did make me think, though, that it was okay once in a while to, like, take a tea bag.

[Grace O'Malley]

Oh, yeah, there you go.

[Natasha Leggero]

But back to the room and. Actually, no. Well, I also had roses in my rider for a long time because I was doing a bit with them.

[Grace O'Malley]

Okay.

[Natasha Leggero]

But then I stopped doing the bit. But then I just liked having them there.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

I kind of liked that the guys in charge of the club would, like, be, like, you know, scrounging to get roses.

[Grace O'Malley]

Like, why the fuck am I gonna get roses? I don't know, pal. Be a better guy if you were a better guy. You know where to find roses.

[Natasha Leggero]

Yeah, they're always trying to find them. So that was kind of funny. And then I started to feel bad for him, so I took it off the rider.

[Grace O'Malley]

That's really funny.

[Natasha Leggero]

But I would like to put something on there. What do you have on yours?

[Grace O'Malley]

I don't have one yet. So I'm curious to see what people. People have. I. I walked into one show and they were like, we. We got. We got that fruit you asked for, and we didn't know what kind of chips you like. So we got all of them. And I was like, I didn't ask for any of these things. I guess someone on my team had put something. They were like. They just threw something on. They got all the chips, and I'm like, this feels gross. This feels icky to me that they frantically picked all the chips out to go get. So I don't like riders so much.

[Natasha Leggero]

It's also such a weird Job where, like, waiters are coming in, trying to, like, get you alcohol before you do your job. It's like, it's the only job that's like that, like.

[Grace O'Malley]

And then.

[Natasha Leggero]

Such a bizarre world.

[Grace O'Malley]

It is interesting.

[Natasha Leggero]

You can make demands before. Before you go.

[Grace O'Malley]

Like, the only other time you kind of have it like that is when you're, like, at a. At a booth, at a club, like a table at a club.

[Natasha Leggero]

Right?

[Grace O'Malley]

Give me. Give me a bottle of. That's the only other time you can, like, have someone, like, go fetch you something. Which is crazy. But. Yeah, I. I don't. I. I get nervous. I. I also feel bad over in January. I tried to do dry January. I'm a. I'm a big drinker, might have a problem. I do, actually, and I'm working on it. And so I tried to do dry January. Didn't work. I have a problem. Totally.

[Natasha Leggero]

How many days did you get through?

[Grace O'Malley]

I did two weeks strong.

[Natasha Leggero]

That's good.

[Grace O'Malley]

It was good. It was good.

[Natasha Leggero]

Do you ever, like. Because I. Some. I just did one for a month. I mean, I wouldn't call myself a big drinker, but I would say I drink daily.

[Grace O'Malley]

Yeah, I drink daily.

[Natasha Leggero]

Like, I like to have a glass of wine every day, and most days.

[Grace O'Malley]

I'm not getting drunk every day, but I do. I've caught myself and, like, with doing standup, I'm the only one drinking at the clubs.

[Natasha Leggero]

Really?

[Grace O'Malley]

Yeah. It's kind of blowing my mind. It's like everyone my age doesn't really drink, especially in New York.

[Natasha Leggero]

Really?

[Grace O'Malley]

My mind. Yeah.

[Natasha Leggero]

Well, one thing I thought helped me is, like, writing myself a letter or, like, writing, like, I, you know, I, Natasha Leggero, am going to do this in exchange for whatever. Like, maybe there's like, a little kind of clarity or something specific that you want to, like, manifest. I do feel like, oh, that's good. Sometimes, like, getting rid of, like, a bad habit, you can, like, try to replace it with something more positive and give yourself an end date and you'll feel really good after it because I think you might find that you have a little insight. I don't know. I'm not trying.

[Grace O'Malley]

No, no, that. That totally makes sense. That's, like, a really great way to go about it. And I'm.

[Natasha Leggero]

It doesn't have to be January. Like, it could just. You could start today and say, I want to do three weeks. Totally, and I want to do it. Maybe it's also try to. This is how you can hack the system. Do it when, like, you know, you have to look really good.

[Grace O'Malley]

Yeah, yeah.

[Natasha Leggero]

By a certain time. So it's like, it's all gonna work out.

[Grace O'Malley]

I don't wanna have red face.

[Natasha Leggero]

Yeah. You know?

[Grace O'Malley]

Yeah, no, that's a really great way of looking at it. I. I recently said the same thing to Burt Kreischer, and he said, oh, just try to be a little bit better every day. And I was like, that's good. He's like, yeah. Like the other day, I.

[Natasha Leggero]

That's hilarious that you're taking not drinking advice from Bert Kreischer.

[Grace O'Malley]

Yeah. Yeah. And you know what? He had me to.

[Natasha Leggero]

He's very compelling.

[Grace O'Malley]

He is. Because he was like, yeah, no, like, I had 10 beers one day. Then I was like, you know what? I'm gonna be better tomorrow. And I had nine. And I'm like, I could totally do that. But this, this seems more long term and probably have a better, better idea.

[Natasha Leggero]

Well, especially now since you're on the scene, you have all these things you want to accomplish. If there's something really big, you know, maybe, just maybe. Just say, I'm gonna try to blank.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

See if it. And then if it works, you'll feel like really powerful.

[Grace O'Malley]

Y. Maybe. And then I'd. Oh, my God. Then maybe one day I'd go sober.

[Natasha Leggero]

You want. Do you want to go sober?

[Grace O'Malley]

No, I don't plan on it. Have you ever gone sober besides that month? Besides that month.

[Natasha Leggero]

But I also like to smoke pot, so.

[Grace O'Malley]

Oh, okay. Yeah, See, I don't have that vice. I have every other vice, but. But weed?

[Natasha Leggero]

No weed.

[Grace O'Malley]

I'm an uppers only gal.

[Natasha Leggero]

Isn't weed an upper?

[Grace O'Malley]

It's a downer for me. It gives me schizophrenia.

[Natasha Leggero]

I see brains.

[Grace O'Malley]

Yeah. Moving on. Was there a specific person that put the fire under your ass to get up and do stand up?

[Natasha Leggero]

You mean for the first time?

[Grace O'Malley]

To get you to. Either for the first time or to get you to pursue it?

[Natasha Leggero]

To get me to pursue it. I was dating again, an older man. I used to always date old dudes.

[Grace O'Malley]

That's fair.

[Natasha Leggero]

And he. This guy was like, really old. Like, I was like 26. I think he was like 50 or something.

[Grace O'Malley]

Oh, wow.

[Natasha Leggero]

And he was like, you should be a comedian. And I. I remember when he said that, I was like. Like, that's the dumbest thing I've ever heard, you know? Like, what was your plan? Rejection. To be an actress?

[Grace O'Malley]

Yeah.

[Natasha Leggero]

Then I saw a girl I knew this girl Melanie Vessi at the Comedy Store, and I had known her from acting school. And I was like, oh, you can just stand up on stage and talk.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

Like, I didn't really know what it was.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

And then I tried it, and it just went, like, way better than I thought. And I just really couldn't believe people were laughing.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

And it was such an amazing feeling, and I was kind of hooked.

[Grace O'Malley]

So you didn't have that, like, when you first started, you didn't have, like, that initial bomb that everyone usually has?

[Natasha Leggero]

No, that came the second time.

[Grace O'Malley]

Okay. Yeah.

[Natasha Leggero]

Then that was, like, a horrid bomb because it was fueled with all this confidence.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

So I thought I was gonna, like. I had this whole plan for the end, and I was just gonna be like, thank you, everyone. You can see me at the improv lab October 16th. And, like, I had this whole. I, like, even booked a show so I could, like, announce it, and I was like. I got off stage. Like, I bombed so bad. It was, like, in a bar, and I was. You know, it was like sailors, and I was trying to do crowd work, and I, like, ended up telling them how bad they smelled. And, you know, everyone was, like, bought, like, just, like, booing me.

[Grace O'Malley]

Yeah. It's the opposite of thank you for your service.

[Natasha Leggero]

It was awful.

[Grace O'Malley]

It just reminds me of, like, like in the 1940s, 1950s, where they had the. The. The showgirls come and perform for the. The military overseas.

[Natasha Leggero]

Yeah, it was like that. But then once I started comedy, I would say in the very early stages, someone who was very helpful was Bobby Lee.

[Grace O'Malley]

Oh, really?

[Natasha Leggero]

He was always around trying to, like, mentor comedians and give them good advice. And, you know, he would always have this, like, great wisdom. Like, he would say, you know, I remember he told me, try to make them laugh before you start talking. He would just say all these, like, things that would make you think about comedy and all these different ways. And. Yeah, he would also say, you know, you're not good until you bomb 50 times, so maybe make sure you're keeping a record of how many times you're bombing. Bombing's good. And so, like, trying to bomb so you could, like, get them out of your system.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

And. And I would go up all the time.

[Grace O'Malley]

Really?

[Natasha Leggero]

I would, like, keep this, like, little diary, and I would make sure I was doing at least seven shows a week. And I would, like. I remember every month, I would, like, tally how many. I have no energy. I would never do this.

[Grace O'Malley]

But this is good, though.

[Natasha Leggero]

But it was the only time in my life I ever became kind of anal rich, attentive.

[Grace O'Malley]

Really? Because. Because. Would you consider yourself a Type A or type B person.

[Natasha Leggero]

What's type B?

[Grace O'Malley]

Free flowing.

[Natasha Leggero]

I suppose I would say I'm very type B when. Except for when it comes to, like, furniture placement.

[Grace O'Malley]

Oh, wow.

[Natasha Leggero]

And how are we doing decor? Oh, you guys are good. I just mean my own.

[Grace O'Malley]

Okay.

[Natasha Leggero]

You know, like, I thought you've been analyzing this the whole time, but, like, you know, I'm. I'm a little particular about furniture.

[Grace O'Malley]

Okay. Just furniture. Okay. Your home.

[Natasha Leggero]

Homes and hotels.

[Grace O'Malley]

Gotcha.

[Natasha Leggero]

And food. I guess I'm actually kind of a snob.

[Grace O'Malley]

Yeah. But that happens later in life. Or later.

[Natasha Leggero]

Later.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

Yeah.

[Grace O'Malley]

That wasn't always the case.

[Natasha Leggero]

No. Because I had, like, you know, a horrible shack.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

So. And, you know, I had bad. But my car is a huge mess.

[Grace O'Malley]

Okay. All right.

[Natasha Leggero]

I think that's a good indicator of, you know, what your personality type is. Is your car.

[Grace O'Malley]

I think so too.

[Natasha Leggero]

Because the people who. With kids and husbands and sharing cars, who can, like, still keep it together. Well, it's definitely impressive though, don't you think? Don't you love being in, like, a clean car? My car's never clean.

[Grace O'Malley]

I just. I. I don't know if I put trust in that.

[Natasha Leggero]

Really.

[Grace O'Malley]

Yeah. Because if it's too clean and you have a. And you have kids and like you said, sharing a car.

[Natasha Leggero]

Yeah. It makes you suspicious.

[Grace O'Malley]

Yeah. You're running a militia over there, I think. I don't know. I'm not sure.

[Natasha Leggero]

That makes me feel better.

[Grace O'Malley]

Yeah. No, you got to be like. You have to have a. A human flaw somewhere.

[Natasha Leggero]

But my husband has, like, the extreme of the opposite.

[Grace O'Malley]

Like, he.

[Natasha Leggero]

He does the Zen pouches.

[Grace O'Malley]

Oh, yeah.

[Natasha Leggero]

And is he just huck the world? Is his. His ashtray? Yes.

[Grace O'Malley]

Well, you could have the latter. My father does dip. And. Yes. And wait, whoa.

[Natasha Leggero]

Dip?

[Grace O'Malley]

Dip.

[Natasha Leggero]

Yeah, and he'll like. They'll be like black stuff in jars. And how did your mom handle that?

[Grace O'Malley]

Oh, well, on the first date, she took a sip of a McDonald's cup, and it was dip. I was told to stop talking about their marriage.

[Natasha Leggero]

Wait, that's interesting. Yeah. My mom does not like when I talk about her.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

And my daughter has also asked me to never repeat. I don't even think it's occurred to her that I would talk about her on a podcast or on stage.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

But she's asked me, like, she hates if I repeat a story to a friend.

[Grace O'Malley]

Oh, really? Oh, so she's gonna hate when it. When it comes to life on a podcast.

[Natasha Leggero]

Well, that is. That is an Interesting.

[Grace O'Malley]

I think 10. You can sit her down for 7, 8, 9. You can. I think you have the upper hand right now. It's like when they start going through puberty is, like, where it gets a little tricky, I'd suppose. Yeah. Before I ask this other question, what are. Have you ever done jokes about your mom and what has she said? And how have you dealt with that?

[Natasha Leggero]

Well. Oh, this is funny, actually. So sometimes I will, like, post things, you know, like when I was on this show, I was on the show Dice, and my mom was texting me that she was trying to get the DVDs of it at the library, you know, And I, like, posted. I posted something on my Instagram, like, our text exchange. And there is like. Like some spy in Rockford where whenever I make fun of my family on Instagram, they send it to her. Oh, because she's not on Instagram.

[Grace O'Malley]

Yeah. Who's the spy?

[Natasha Leggero]

I don't know. And I wanna know. I have. I have some. I have some inklings, but her friend.

[Grace O'Malley]

Diane, I feel like her name's like, Diane.

[Natasha Leggero]

Someone is, like, feeding her. Yeah. She was not. She was not into it and very upset. And I think it's. Now that I think about it, probably the reason for sometimes our money. Months long of not talking.

[Grace O'Malley]

Oh, yeah, yeah, that'll. That'll happen.

[Natasha Leggero]

Yeah. It's hard because, you know, I was reading this, or I was watching this David Sedaris masterclass, and he's like, as a writer, every single person in your life is fair game.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

And he was even interviewing his sister about it, and he has, like, not Amy, but, like, he had another one of his sisters, like, who he writes about a lot, and asking her, and she's like, well, you know, I told you a few things I didn't want you to say, but, you know, people just sort of get used to it.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

And I don't know, she's. She does. I mean, but she's private, so I get it.

[Grace O'Malley]

I think I. My mom's on the opposite end of. She wishes I'd put more about her.

[Natasha Leggero]

Oh, really?

[Grace O'Malley]

Yeah.

[Natasha Leggero]

She eats it up.

[Grace O'Malley]

My dad has told me, if you're gonna do jokes about me, at least be funny. I'm like, oh, wow. All right. Pretty sure they're funny. Just because they're about you, you don't think they're funny? I think that's where the line gets crossed. But, yeah. No, it's like a slippery slope when it comes to people in your life.

[Natasha Leggero]

He sounds like comedy gold, to be honest.

[Grace O'Malley]

Oh, he is. Classic. I'm just trying to figure out the best way to put him in. He is. There is something there.

[Natasha Leggero]

You should get him on the pod.

[Grace O'Malley]

I new career and not interested in getting canceled anytime soon. And he will be. Guilt of association. Canceled. Yeah, that is.

[Natasha Leggero]

Wait, what's your old career?

[Grace O'Malley]

Waitressing. That was like. That was what I was doing before.

[Natasha Leggero]

I see.

[Grace O'Malley]

But, yeah, I was waitressing then. A podcast. You know, podcast. Stand up.

[Natasha Leggero]

Yeah, Podcasting is a little better than waitressing.

[Grace O'Malley]

Yeah, it's been. I wait to switch up.

[Natasha Leggero]

I waitress for so many years. I just used to have, like, dreams about taking people's order. Like, it just feels like, oh, my God, it just sucks. Your life force, like, your creative energy is being, like, stolen 1,000%.

[Grace O'Malley]

And. And for whatever reason, in my horror nightmare dreams where I forget to put an order in, is the staff there? They're. It's like they are family. And I never felt a part of the family at this. At any of my waitressing jobs. Really. I was just like some kid that they wished wasn't around.

[Natasha Leggero]

You had bigger, bigger things coming on the horizon.

[Grace O'Malley]

That's what it is. I no longer smell like tartar sauce. And that's. That's huge. This segment is called Bombed. Do you recall the first time you were heckled negatively? And how did you handle it?

[Natasha Leggero]

I remember performing in Atlantic City. And, you know, Atlantic City has a certain climate.

[Grace O'Malley]

Yeah. It's a tough vibe over there.

[Natasha Leggero]

Yeah.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

And this guy was like, hey, wrap it up. He was, like, looking at his clock, doing this.

[Grace O'Malley]

That's brutal.

[Natasha Leggero]

And I was just like, you know, because when you're starting out, too, you don't really know how to respond to them. So I think I was just. I would always just try to pretend like I didn't hear it, which is not good. That's not a good way to. To deal with it. But it's hard. I mean, what's really great is getting a fan base so that there aren't people in your crowd who have no idea who you are and don't care and don't like you.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

Oh, another woman once, I was at the. I was at Caroline's on Broadway in New York, and I used to have this joke. I didn't usually open with it, but I decided to open with it because I was, like, going through this phase where I was, like, mixing all my stuff up. Yeah, it was something like, you know, they're giving out free AIDS tests at the dmv. You know what's worse? Having to wait in line at The DMV or finding out you have AIDS or something like this. And this girl stands up, and she's like, my brother died of aids.

[Grace O'Malley]

Like, oh, God.

[Natasha Leggero]

In the front row.

[Grace O'Malley]

Jesus Christ.

[Natasha Leggero]

And I was like, I'm sorry, man.

[Grace O'Malley]

So which one's worse?

[Natasha Leggero]

But then I had, like, 45 minutes left, so that was really bad.

[Grace O'Malley]

And did she stay for the rest of the set?

[Natasha Leggero]

No, she walked out. And I think I somehow got everyone to cheer her leaving, but it was. Was definitely a challenge.

[Grace O'Malley]

Yeah, that's a tough one. Did you respond at all, or.

[Natasha Leggero]

I think I was very apologetic because obviously, you know, she. For all I know, she came to the comedy club to forget about it.

[Grace O'Malley]

Yeah. Yeah, totally.

[Natasha Leggero]

And, you know, it's hard. It's hard because comedians, you know, sometimes we're very jaded, and, you know, we're. We're doing this because we can't take anything seriously.

[Grace O'Malley]

Yeah, that's the problem.

[Natasha Leggero]

So much serious things have happened to us that we, you know, we're immune, and so we're just kind of, like, throwing out there. So.

[Grace O'Malley]

Yeah, I commend you for taking a step back and just playing. Hey, my. My bad. Because it's hard because you could have leaned into it, and then you're just a fucking asshole. So it's a slippery slope there.

[Natasha Leggero]

Yeah, it's. It's hard.

[Grace O'Malley]

Yeah. All right, I'm gonna move on. Is there a joke from your first set that you think wouldn't get a laugh now?

[Natasha Leggero]

I mean, none of it would.

[Grace O'Malley]

No, I doubt it. Really?

[Natasha Leggero]

I was, like, making fun of Slaying. I think there's some things in my frame, first set that might get me canceled.

[Grace O'Malley]

Oh, that's good. Yeah. No, I mean, that's just time, right?

[Natasha Leggero]

Right.

[Grace O'Malley]

That's nothing to do with you. That's time and the way things evolve.

[Natasha Leggero]

Yeah. I mean, I honestly don't remember much of it. It'd be fun to watch. I think I have a VHS tape lying around somewhere.

[Grace O'Malley]

You do.

[Natasha Leggero]

And I also remember I wanted to, like, dress up in this, like, red dress with, like, this, like, leather cap.

[Grace O'Malley]

You're always dressed to the nines. That's.

[Natasha Leggero]

Well, that. That happened later. Yeah, because, like, I had this, like, smart instinct after, you know, for my first set to, like, dress very, like, just blend in. Because I was like, if I bomb, I don't want to be bombing in, like, a leather hat.

[Grace O'Malley]

That's fair.

[Natasha Leggero]

Right? So that, you know, I. I just tried to keep it. Keep it real.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

Basic.

[Grace O'Malley]

That's fair. Oh, how do you Manage work and romantic relationships in your career. As you tour, you have a podcast with your husband. You guys ever like getting a bit of like a squabble and then you can't record or.

[Natasha Leggero]

Well, you know, our, our podcast, the Endless Honeymoon podcast we, my husband and I do together. And people will call in and ask for relationship advice. And, you know, he's been an AA for 20 years and I've, you know, dated 50, 50 year olds. So, you know, so we just have a lot of experience. But sometimes I'll use the podcast as a way to sort of hijack him with something.

[Grace O'Malley]

Oh, that's fun. I like that he's on the spot.

[Natasha Leggero]

And then he's on the spot and then we'll end up, you know, posting it and then everyone agrees with me. And it's usually.

[Grace O'Malley]

That's better than couples therapy.

[Natasha Leggero]

Way better.

[Grace O'Malley]

Oh my God. And it's good to get ahead of it.

[Natasha Leggero]

Oh, yeah.

[Grace O'Malley]

Oh, that's great.

[Natasha Leggero]

I'm so glad that it's a resource for me now.

[Grace O'Malley]

So what is your demographic on that podcast? Is it mostly women or.

[Natasha Leggero]

I would say it's mostly 30 year old women who are trying to figure out if the guy that ghosted them might secretly like them. And I have to tell them no.

[Grace O'Malley]

Yeah, that's got to be hard for them to hear. I mean, that's especially coming from your mouth. It's so, it's so honest and like to the point I, I'd be, I'd be hard.

[Natasha Leggero]

And I think you have to be real with people because, I mean, it's like never before have men had so many options. You know, they can just pick and choose and they, they're at, you know, men and women often have. They're just at different levels with.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

Wanting a relationship, wanting to hook up. I think a lot of the men in LA secretly think that they're gonna maybe date Emma Stone at some point or, you know, they, they're like holding out for like someone they're never gonna get.

[Grace O'Malley]

You'll do for now until I get my A list.

[Natasha Leggero]

Exactly. And so, and a lot of men have like made it so that, I mean, I know like 50 year old men who have like made their cutoff point 29.

[Grace O'Malley]

Jesus Christ.

[Natasha Leggero]

And so it's like there's so many like beautiful, hot, interesting, charming women who aren't even like getting. But then it's like, why would they want to date someone who is.

[Grace O'Malley]

Who's looking for a little hot little thing?

[Natasha Leggero]

The thing too is I think girls also feel like oh, I'm, I'm getting old. They all want young people, but it's like, they want young people not because they're so much hotter. It's because young people are more impressed with them.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

If you've done like one indie film that you helped produce, like a 23 year old thinks you're like, really?

[Grace O'Malley]

That's Corsair.

[Natasha Leggero]

Really successful. Whereas, like, I'm like, oh, okay, well, how do you make your money?

[Grace O'Malley]

Like, sick. That must. You have a trust fund? You must have a trust fund.

[Natasha Leggero]

Right? So I would say the demographic is mostly female, though, so that's huge for your case. Oh, yeah. That is probably why they agree with me. But we have a lot of couples and, you know, it's, it's, it's international. I don't know. I mean, we've. There's a lot of different types. Who do you hope to speak to on this podcast?

[Grace O'Malley]

I. This isn't very feminist of me, but I am. I'm hoping to get a little bit more of a male audience.

[Natasha Leggero]

Really.

[Grace O'Malley]

My shows feel like a sleepover, which is awesome. It's a slumber party with all the ladies, lady gals, and I love that. But all my openers get to go home and go fuck somebody, and it's just a seat full of vagina. So if, if with this podcast, I could reach a male a little bit. You know, everybody wants 50. 50.

[Natasha Leggero]

Yeah.

[Grace O'Malley]

And mine is 97% women.

[Natasha Leggero]

Oh, okay.

[Grace O'Malley]

Yeah. So, which is funny.

[Natasha Leggero]

I prefer speaking to women. I mean, I'm on. I'm on three text chains that I contribute to a lot, and two of them, Two of them were all women. But recently a man has come into the mix on both of them.

[Grace O'Malley]

Oh, it's. It's off in the vibe. Up.

[Natasha Leggero]

Yeah, yeah, it's really like off now. And so straight man or gay man? Straight.

[Grace O'Malley]

Okay, that's. Yeah, that's a. That's a whole pivot. You need a new group.

[Natasha Leggero]

I know the group with him in.

[Grace O'Malley]

The group, without him. That's kind of how it goes.

[Natasha Leggero]

Yeah. It really did kind of like ruin. Definitely. I don't want to talk to these, These chains anymore.

[Grace O'Malley]

It kind of fucked everything up.

[Natasha Leggero]

It did.

[Grace O'Malley]

That's fair. Just off the top of my head, you lived in New York, you lived in la, and you. You do. You're great with relationship advice. Which one was better for dating?

[Natasha Leggero]

Oh, I think New York is way better for dating.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

Well, because you're out being seen. Yeah, that's true to me. And my husband will always make fun of me because I'm always giving the advice, like, get a Village Voice. See what's going on. He's like, you sound like an old lady.

[Grace O'Malley]

But I'm like, what is a Village Voice?

[Natasha Leggero]

A Village Voice. Well, you can do it online now, but it used to be when I lived in New York, but, you know, and anything that has a calendar section, like, where are the cool things?

[Grace O'Malley]

Oh, yeah.

[Natasha Leggero]

Where you have some things that you're interested in, whether it be, you know, opening to a movie, maybe the directors coming to speak.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

An art. An art exhibit that you're into.

[Grace O'Malley]

So much fun.

[Natasha Leggero]

You know, antiques at the farmer's market. Like what? Wherever you can go where, like, things that you're interested in and walk around and like, actually send sense people's vibes.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

I mean, how can that not be the future? We already saw that. It doesn't work to just like, scroll and text with some random dude for 5 days until maybe he asks you out for a coffee, but probably doesn't. Yeah, that doesn't work either.

[Grace O'Malley]

Reschedules, probably. Oh, yeah, A lot of rescheduling going on. Cold feet.

[Natasha Leggero]

Do you, like, do a dinner date for the first date?

[Grace O'Malley]

I have been on three dates. I have never had a boyfriend. I'm 26 years old.

[Natasha Leggero]

You never had a boyfriend?

[Grace O'Malley]

I stand with the ladies who haven't.

[Natasha Leggero]

That's so cute.

[Grace O'Malley]

Just like, not like something that, like, really. Of course I would love, but I haven't had, like, the opportunity thus far. So three dates, they were all. I think. I think they just wanted to get drinks. I. I offered to get food. They were like, nah, let's just do drinks. And I was like, I'm like, fasted all day, and so now I'm gonna get drunk.

[Natasha Leggero]

But, yeah, I've never asked a guy out, and I do feel like that's something that I've noticed that younger people will do, and I think that's cool.

[Grace O'Malley]

I one time I want people to do that because in high school, I asked a sophomore to my junior prom, and he said, oh, I have a basketball tournament. Sorry. And I was like, oh, that's cool. And he ended up going with one of my friends. Yeah, so that stunk. No, it's all good. But you know what I did recently? There's these meetups where you go and it's all single people.

[Natasha Leggero]

Cool.

[Grace O'Malley]

And it's kind of like speed dating, but not really. You just kind of talk to everybody, casually drink, drink. And then at the end of the night, after filling out a Survey. We got like a 3, 2, 1, countdown. And you walk. Like, your phone tracks you to the person that you match with. And, like, you'd have to walk to them.

[Natasha Leggero]

That's cool.

[Grace O'Malley]

It was super cool. If it were the type of fellas who signed up for that are not my type of fellas. That the guys.

[Natasha Leggero]

Literally. What was the theme? Like, how did they. How did they get people there?

[Grace O'Malley]

I. They always have so many. They said they always have so many cool success young women, but it's like pulling teeth trying to get the guys to come. Because it's not cool.

[Natasha Leggero]

Right?

[Grace O'Malley]

Because if you told. Like, I feel like I can picture, like, if. If one of my guy friends were like, yeah, I'm gonna go do this date and thing, they're like, that's weird.

[Natasha Leggero]

Guys don't need to do it.

[Grace O'Malley]

Yeah, they don't need.

[Natasha Leggero]

Because they just have, like, this, like, enormous selection. Yeah, like, that is. They're not supposed to have that without doing any work.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

It used to be they at least would have to do some work for it.

[Grace O'Malley]

Open that door. Door.

[Natasha Leggero]

Yeah. Right.

[Grace O'Malley]

I would. I would take this jumpsuit off right now if somebody opened a door for me. So the bar's low.

[Natasha Leggero]

You just want a door open. Well, so did you match with anyone at the meetup?

[Grace O'Malley]

Yeah, yeah, yeah. I. I turned to another girl I met there, and she was like, hey, you having fun? I was like, yeah. She's like, can you go to the bathroom? I was like, yes. And we just never came. We never went back. We did.

[Natasha Leggero]

It was a fun.

[Grace O'Malley]

Yeah, we made friends.

[Natasha Leggero]

That's cool.

[Grace O'Malley]

And then another thing I did was I went on a live dating show where you're blindfolded, they're supposed to play matchmaker with you. And I had. I had. They made me kiss him on stage. I said I was open to it beforehand, but. But as soon as it happened, of course I was like, oh, this is. I don't want to do this. A bunch of people watching. I did. I did end up kissing him on stage and taking the blindfold off, and it was just, you know. You know, it was no Taylor Swift. Sparks fly, you know?

[Natasha Leggero]

Right.

[Grace O'Malley]

Yeah. Sorry. That was a ramble. You ever do anything, like a speed dating kind of thing or anything like that?

[Natasha Leggero]

I feel like. Like I was married, like, right before online dating.

[Grace O'Malley]

Like, oh, that's cute.

[Natasha Leggero]

I mean, of course there was, you know, eharmony and a few things, but it wasn't really a thing yet.

[Grace O'Malley]

Yeah, totally. They also had that. What is that? That. That website where you could cheat on your wife. Holly Madison. No, That's a playboy.

[Natasha Leggero]

Ashley Madison.

[Grace O'Malley]

Ashley Madison, yes.

[Natasha Leggero]

That was so good. That was a good one.

[Grace O'Malley]

I wish I was around for that. I would have. I'm getting to that point where Ashley Madison's kind of. Of probably gonna be my thing.

[Natasha Leggero]

I mean, you're young.

[Grace O'Malley]

Yeah. You know, you gotta do what you gotta do.

[Natasha Leggero]

When I was your age, I was stealing potatoes in Australia.

[Grace O'Malley]

That is a good story, though.

[Natasha Leggero]

A man who looked like a. Yeah.

[Grace O'Malley]

What did he look like? He.

[Natasha Leggero]

Well, the first day I. The first time I met him, he walked into the bar I was working at, and he looked really cool. He kind of looked like Mick Jagger. Like, kind of, like old, but, like, weathered, haggard.

[Grace O'Malley]

Seen some shit?

[Natasha Leggero]

Yeah. But like. Like, you know, he had this, like, school jacket on from, like, Harvard. Like, you know, like, he was very.

[Grace O'Malley]

Stole off a student.

[Natasha Leggero]

Yeah, Like. Like, he was like. Oh, you know, like the Oxford stripes. It was like some sort of European, like, Ivy League jacket. Then when I agreed to go on a date with him, he was wearing a Cosby sweater.

[Grace O'Malley]

Oh.

[Natasha Leggero]

And I was so embarrassed.

[Grace O'Malley]

Oh, so he's a. Now. Now he's a funky con artist. Yeah.

[Natasha Leggero]

He just didn't really have taste. So I, like, accidentally saw him look cool. But by the time, you know, second date, I was just. I was already, like, swooning.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

Because I had only dated, like, young guys. Like, I thought it was so cool. He knew about wine.

[Grace O'Malley]

Oh, yeah.

[Natasha Leggero]

Yeah. Like, I wanted someone who, like, what's.

[Grace O'Malley]

This guy sommelier is like?

[Natasha Leggero]

Yeah. Like, we would walk into a restaurant. Like, I remember we went to Tavern on the Green.

[Grace O'Malley]

Ooh. And they.

[Natasha Leggero]

We got there in New York, in Central Park. Like, very popular restaurant. Very, you know, fancy, touristy. But we got there, and he asked the woman, he was like, you know, table for two. They're like, we have no tables. And I went to the bathroom, and when I came back, I swear to God, he was kissing her hand. And she was like, right this way, sir, and sat us by the fountain.

[Grace O'Malley]

Oh, my God.

[Natasha Leggero]

I know he didn't have money, so I don't know how he would get people to do things for him, and I don't know how. And it was always like, older ladies.

[Grace O'Malley]

There's a reason they call him Car. An artist.

[Natasha Leggero]

Right.

[Grace O'Malley]

Because there's art in that to sway someone's mind like that.

[Natasha Leggero]

Truly.

[Grace O'Malley]

It's kind of really sick thing to be able to do unless you're doing it to, you know, young women. But.

[Natasha Leggero]

Well, it definitely turned Me on.

[Grace O'Malley]

Yeah. No, I mean, you had a blast. Six months of pure fun in Australia, I suppose. A whirlwind, even.

[Natasha Leggero]

I even talked my mom into paying for us to come back to America because we had used all of our money. And she. And then this was great, because I was like, okay, Mom, I just. And I lied. I said, I just need my. My flight. It's $2,000. And so she gave me $2,000, and I was like, okay, Alex, I can get us both tickets back to America from Australia. And he's like, what? We're not stopping in Koh Samui. And, like, he was so mad that we weren't gonna stop in Thailand, and he's like, I am not. And then we would go, and then I.

[Grace O'Malley]

Basically free until anyone says, what? Thailand.

[Natasha Leggero]

We went to Thailand. And then I remember he would be like, what? We don't have a. We don't have a bungalow right on the ocean. He would just get so mad if he didn't get, like, the best.

[Grace O'Malley]

Oh, goodness.

[Natasha Leggero]

And. But he didn't want to pay for it.

[Grace O'Malley]

Oh, are you sure I would pay for it, or are you sure your daughter's not his. I wasn't sure how that one was gonna go. Thank you for laughing.

[Natasha Leggero]

But I will say I met that guy before I started standup, and I do feel like I took a little bit of him with me on stage.

[Grace O'Malley]

Oh, I love that. And so he wasn't good for nothing anyways.

[Natasha Leggero]

Exactly.

[Grace O'Malley]

He brought something good out of it. It's so funny that you can come full circle now. You have a beautiful family, and you work really hand in hand with your husband, and we're working on your daughter. She's a little bit of a snob, but one day we'll get there, and. And I don't. Like, how do you. How do you balance it all?

[Natasha Leggero]

I don't.

[Grace O'Malley]

Yeah, you can't.

[Natasha Leggero]

I mean, sometimes I'll, like, make a list of, like, 10 things that I really want to do in a day. Every day.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

And I'll, like. And I keep it by my, like, fireplace. And sometimes I'll glance at it throughout the day and be like, okay, well, at least I did those four things. Yeah, that's huge because, like, every day, I want to exercise and play tennis. I'm not saying I want to do this every day.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

Yeah, do stand up something new. Read with my daughter for 20 minutes, meditate. Like, there's just so many things that make me feel good that, you know, are so easy to just forget about.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

So I think trying to think about the things that you really want to do that are. That make you feel good, and just making sure you can hit a bunch of them every day as much as you can.

[Grace O'Malley]

That's huge. And that's smart to keep a list because it's so easy to just. Just do what you have to do and not what brings you joy, as corny as that sounds. Yeah.

[Natasha Leggero]

And then when you also. When you look at the list, you kind of feel good. You're like, oh, I actually. I did, like, four of those things today.

[Grace O'Malley]

Yeah, right. It's good stuff. I want to start taking lists. Are you an Adderall person?

[Natasha Leggero]

I have definitely taken Adderall, but only because a friend with a prescription gave it to me. We were trying to, like, finish a writing deadline.

[Grace O'Malley]

Okay, so you're just. You're just. But I liked Free Ball in this.

[Natasha Leggero]

Yeah.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

And it was definitely fun.

[Grace O'Malley]

I just need it, and it. Sometimes it doesn't.

[Natasha Leggero]

You're on Adderall.

[Grace O'Malley]

Oh, yeah.

[Natasha Leggero]

So why do people say when they. They're like, oh, but it actually slows me down is. Are you one of those people? Like, Adderall actually doesn't make you speedy.

[Grace O'Malley]

It doesn't make me speedy. It. If anything, it'll just get my. Not today, apparently. But it'll usually help my thought process and, like, the way. Way I speak and the way I get things done. I guess, like, the list is in my head that you make, and I can, like, organize it. If not, it's scatterbrained. And I.

[Natasha Leggero]

It's like. It's, like, good. If you like to party while you make to do lists.

[Grace O'Malley]

Absolutely.

[Natasha Leggero]

It's kind of like that.

[Grace O'Malley]

Yeah. I've kind of got, like, a smooth.

[Natasha Leggero]

Brain going on, but it really does activate something.

[Grace O'Malley]

Something's there.

[Natasha Leggero]

I would love to take it.

[Grace O'Malley]

I take it like an antidepressant, actually. Really? If I don't. If I. And see, that's where people call it addiction, but it's prescribed, so it'd be.

[Natasha Leggero]

Fun to do a podcast on Adderall, actually.

[Grace O'Malley]

Oh, my God. Yeah.

[Natasha Leggero]

Is that what we're doing right now?

[Grace O'Malley]

I mean, that's what. There is one half of us doing Adderall podcasting live in the flesh. And I think I'm gonna have to up the dose because you can't even tell. But you kind of touched on this, but not really. Does your daughter roast you?

[Natasha Leggero]

Not yet. She's kind of, like, understanding what a joke is.

[Grace O'Malley]

Okay. That's a fun stage.

[Natasha Leggero]

Exactly. Sure. But she does like funny word play. She's very verbal.

[Grace O'Malley]

I mean, she sounds smarter than I already.

[Natasha Leggero]

She really is.

[Grace O'Malley]

Yeah, I can tell.

[Natasha Leggero]

She's awesome.

[Grace O'Malley]

Yeah.

[Steve Buscemi]

Hi, this is Steve Buscemi. You know, the actor. Well, now I'm an actor and podcast host. From Piece of Work Entertainment and Campside Media in association with Olive Productions, comes Big Time, an Apple original podcast. Each episode follows the story of one misfit with big dreams who isn't afraid to bend a few rules or take a shortcut to get there.

[Grace O'Malley]

Well, who steals bees? I was duped.

[Natasha Leggero]

I shoot you in the leg.

[Steve Buscemi]

This is Big time. Follow and listen on Apple podcasts.

[Natasha Leggero]

Ever since switching to T Mobile, something weird has been happening. I get to cut lines.

[Grace O'Malley]

Oh, right this week way.

[Natasha Leggero]

Who, me? I can stream shows at 30,000ft and I was able to buy reserve tickets for my favorite band.

[Grace O'Malley]

It's not just you. With T Mobile, everyone can get VIP status. That means access to exclusive events and experiences just for being a customer. At t mobile, VIP means. Y ou check out the VIP treatment@t mobile.com benefits. This segment's called Jokes in my Notes. Basically, you don't have to if you don't want to, but I've been having each guest kind of go through their. Their Notes app if that's where you keep your jokes, and see if there's a premise there that you've either left alone or won't use.

[Natasha Leggero]

You want me to go through it?

[Grace O'Malley]

If you. If you want to.

[Natasha Leggero]

This is what I hate. You pill out your phone and then you're like, I know, right? The vortex. Okay, let me look at my notes. Hold on. I hate the Notes app because half of it is me trying to figure out how to stand up to this person who's harassing me. And then the other part is joke premises.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

So I have to sit here and try to decipher, which is bunch of giraffes.

[Grace O'Malley]

If you try to stand up for yourself. Yeah, no, I get that.

[Natasha Leggero]

I wanted to do a joke about how, like, as you enter perimenopause, you kind of look around and you are very confused with your choices. Like, because you're just kind of like, what? And part of it is, as you get older, the estrogen leaves your body. And another word for estrogen is tolerance. And then one of the things. And. And if you look up the symptoms of perimenopause, it's so horrifying. It's like every single bad thing you can think of. But then someone just told me recently one of the Things they have from. It is bur mouth syndrome.

[Grace O'Malley]

Oh, what the fuck?

[Natasha Leggero]

I wanted to do a little research on that.

[Grace O'Malley]

That's good. I like that. That's a great angle right there.

[Natasha Leggero]

Sounds pretty crazy, right? Burning mouth syndrome. I mean, is that.

[Grace O'Malley]

Is that where you just can't stop telling people how much you can't stand them anymore? Like, oh, sorry, I'm burning mouth syndrome?

[Natasha Leggero]

Yeah. I don't know. I haven't gotten around to looking it up.

[Grace O'Malley]

That's good. I really like that.

[Natasha Leggero]

I think it's funny. And also, Grace, you have been great with the quality of. Not only do you say funny things, but you say things funny.

[Grace O'Malley]

Oh, thank you.

[Natasha Leggero]

Thank you. And that is a very important thing for a comedian. So I don't know. I think you can pull a lot off.

[Grace O'Malley]

My favorite thing about your set, and just you in general, is the way you talk. So to hear you say that is huge. It's like, it makes the joke sound so classy, elegant, and, like, just off the cusp. And I. I like. You could be saying, like, toilet water, but the way you say it, it's like, it's.

[Natasha Leggero]

Well, I'm glad you say that.

[Grace O'Malley]

It's hard to explain.

[Natasha Leggero]

Sometimes I'll hear someone and I'm like, is that me? And it's like the Kardashians. Because I feel like I've lived in LA too long, that I kind of have, like, California speak.

[Grace O'Malley]

I don't really pick up on that.

[Natasha Leggero]

Okay. Yeah, no, it's like, I definitely think I sound like Khloe Kardashian or something.

[Grace O'Malley]

I don't care. Unless you want to sound like that. I'm gonna tell you the truth right now. I don't think you sound like that at all. No, I think you sound. You've got, like, a very great way that you announce C8. It's. That's a weird compliment to give somebody, I suppose. Hey, listen, I'm learning. I grew up Irish Catholic. We don't, like. We don't express good emotions very well. But I am thrilled to have you on. And I have one last question.

[Natasha Leggero]

Okay.

[Grace O'Malley]

What is your usual walkout? So, song or current walkout song?

[Natasha Leggero]

Well, my current walkout song is this song called Heated by Beyonce because she's like Coco Chanel, and I just like coming out to, like, all the brand names. That was kind of funny.

[Grace O'Malley]

I really like that.

[Natasha Leggero]

But I have to say, I feel very much like everyone obsessed with Chapel Ron and so. And I'm really listening to, like, her new album, so I feel like there's got to be something in there that's That I would like. But also, you know, it just depends, you know, Like, I used to come up to, like, don't want no short dick, man. Like, every. Every season, I'll hear. It's always something new.

[Grace O'Malley]

Yeah.

[Natasha Leggero]

That I think will be funny. And then. But I always want them to play it at the end, too.

[Grace O'Malley]

Yeah. Start at the top and then played at the end to walk out.

[Natasha Leggero]

Yeah. Like, I have this joke right now where I'm making fun of kids. Bop. And so do you know about that? You know about kids. So you're like, I listened to it 10 years ago.

[Grace O'Malley]

Who do you. Who do you think was on the.

[Natasha Leggero]

But you know, they have one for Wing, for Wap.

[Grace O'Malley]

Oh, wow.

[Natasha Leggero]

The Cardi b song. It's called Wings and Pizza. And so I always want them to play that at the end of my set. You just kind of play around, and I like that. See what'll be funny.

[Grace O'Malley]

That's funny. I. I just wanted to thank you so much and thank you.

[Natasha Leggero]

This was really fun, and you're doing a great job, and I like your.

[Grace O'Malley]

That's the mom in you. That was really sweet. That's a nice way to say it.

[Natasha Leggero]

You're so funny.

[Grace O'Malley]

Do you have. You want to promote your podcast or whatever?

[Natasha Leggero]

Yes. Listen to our podcast, the Endless Honeymoon Podcast. We also have a secrets hotline. You can call us and leave your deepest, darkest secrets. And me and my husband and some famous comedians will make fun of them. We'd love to have you on now that you're famous.

[Grace O'Malley]

I think I'm going to call in, like, unironically and ask a few questions. I'm going to have to hide my voice. I'll do, like, a voice translator or something. Well, thank you so much. I really appreciate it. And I don't know how to close these. Thank you. Welcome, ladies and gentlemen, to Mario's Bistro.

[Natasha Leggero]

The special tonight is the beef carpaccio.

[Venmo Advertisement]

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[Steve Buscemi]

Hi, this is Steve Buscemi. You know, the actor. Well, now I'm an actor and podcast host from Piece of work. Entertainment Entertainment and Campside Media in association with Olive Productions comes Big Time, an Apple Original Podcast. Each episode follows the story of one misfit with big dreams who isn't afraid to bend a few rules or take a shortcut to get there.

[Grace O'Malley]

Well, who steals bees? I was duped.

[Natasha Leggero]

I shoot you in the leg.

[Steve Buscemi]

This is Big Time. Follow and listen on Apple Podcasts.

[Natasha Leggero]

Ever since switching to T Mobile, something weird has been happening. I get to cut lines.

[Grace O'Malley]

Oh, right this way.

[Natasha Leggero]

Who, me? I can stream shows at 30,000ft and I was able to buy reserve tickets for my favorite band.

[Grace O'Malley]

It's not just you. With T Mobile, everyone can get VIP status. That means access to exclusive events and experiences. Just for being a customer At T Mobile, VIP means y ou check out the VIP treatment at T mobile.com benefits.