Charlie Puth or Charlie Tooth w/ Alison Leiby

Summary

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Podcast Summary – The Nightly: "Charlie Puth or Charlie Tooth" w/ Alison Leiby

Podcast: The Nightly
Date: June 8, 2026
Host(s): Josh Gondelman & Alison Leiby (guest co-host)
Theme: Playful, meandering, cozy late-night chat focused on serendipitous city encounters, karaoke mishaps, celebrity run-ins, and the unique joys of group games—ideal comfort listening for winding down at night.

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Episode Overview

This episode finds Josh Gondelman and comedian Alison Leiby cozied up in the Nightly “pillow fort” for gentle, witty banter. The theme revolves around the odd joys of late-night city life—spontaneous connections, funny brushes with fame, and the sleepy randomness that comes from just letting conversation wander.

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Key Discussion Points & Insights

1. The Ever-Present Sleepiness of Adulthood

• Both Josh and Alison joke about being perpetually tired, blurring the lines between day and night.
  • “Always being sleepy, though, doesn't really tell me what time of day it is.” (Josh, 00:53)

2. “Surprise Paul!”: Serendipitous Restaurant Reunion

• Josh shares a story about accidentally running into his friend Paul (of the musical comedy duo Paul & Storm) at a New York restaurant, culminating in a group of friends secretly sending over celebratory Shirley Temples and a four-person cheers from across the room. (01:02–03:25)

3. Karaoke Antics and the Joy of “Bad” Singing

• Both delightfully reflect on raucous, high-energy karaoke with friends—focusing on “percussion-adjacent screaming” and the secret pleasure of being bad at singing.
  • “I just know I can't sing well. So I'm like, what else can I provide here? Kind of being like percussion adjacent or something?” (Alison, 03:54)
• Alison’s Cher impression and the “magic number” of three for karaoke groups gets a shout-out.

4. Celebrity Sightings: Greta Gerwig, Mel Brooks & the Art of Fitting In

• The conversation shifts to surreal party and event moments where genuine celebrities show up, like seeing Greta Gerwig at Zara’s book event.
  • Memorable moment: Greta Gerwig validating her identity by emphatically exclaiming “Yeah, Sacramento,” when California is mentioned. (05:21)
• Josh shares regret at missing Mel Brooks at an Emmys party.
  • “Most jealous I’ve ever been of anyone for any reason.” (Josh, 06:56)

5. The Low-Key Celebrity Lifestyle in NYC

• Both hosts marvel at celebrities who can hang in Brooklyn bars “without an entourage,” and reflect on the magic of Brooklyn’s effortless mingling.
  • “I always have a lot of admiration for a famous person who rolls with no entourage.” (Josh, 07:36)
• Discussion on how “low-stakes famous” people (like Alison at a local spot) get approached, versus “too famous” folks who remain unbothered. (09:09–10:17)

6. Recognition in the Wild: Concerts, Sales, and Finding Your Crowd

• Josh describes being recognized at concerts, sharing funny anecdotes about how people sometimes don’t approach, or everyone looks just like him at a particular show. (10:17–11:31)
• Alison humorously notes she was spotted at the Rachel Comey sample sale: “Everybody there was me.” (11:31)

7. Online Shopping as a Gamble

• They riff on the risky thrill of buying final sale dresses online, likening it to gambling.
  • “Final sale, no returns is like her version of online gambling.” (Josh, 12:07)

8. Group Gambling: Dice Games and the Social Side of Risk

• Alison discusses her newfound partiality for casual dice games with friends, enjoying the fun of low-stakes risk and communal play.
  • “It just puts some stakes into a game that otherwise has, like, no stakes.” (Alison, 13:55)
• Both discuss the camaraderie of craps at casinos (versus competitive, solo games like poker or blackjack).
  • “Craps is fun…because everyone's winning is contingent on the person rolling.” (Josh, 14:42)

9. Learning Craps (and Not Being Good at It)

• Josh laments his inability to learn craps: “Whenever someone has tried to teach me, my body has rejected it. Like the wrong blood type.” (14:19)
• Both delight in the idea of rooting for friends (and being cheered for minimal effort), revealing a lot about their desire for attention without risk.
  • “I would like people to clap and cheer for me for exhibiting no skill.” (Josh, 16:45)

10. The Comfort of Community in the City and the Suburbs

• Warm reflections on the unique, comforting sense of always running into people you know—or famous people—in New York versus the more mundane small-town version (running into parents at CVS).
  • “I love the feeling of everybody’s here. I feel very comforted by that.” (Josh, 18:46)

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Notable Quotes & Memorable Moments

• On Sleepiness and Time:
  “Always being sleepy, though, doesn't really tell me what time of day it is.”
  — Josh (00:53)

• On Greta Gerwig Sighting:
  “If I were trying to write a line of dialogue that would signal to the room that the person you think is Greta Gerwig is actually Greta Gerwig, she would bring up Sacramento.”
  — Josh (05:21)

• On Being Recognized in Public:
  “I have been recognized at the Rachel Comey sample sale. Like, everybody there was me.”
  — Alison (11:31)

• On Online Shopping as Gambling:
  “Final sale, no returns is like her version of online gambling.”
  — Josh (12:07)

• On Craps Enthusiasm:
  “He is a craps enthusiast in that it is a casino game where instead of being mad at the people around you or trying to win money from them, everybody kind of gets in the inner groove together and cheers for each other.”
  — Josh (14:42)

• On Desire for Applause Without Risk:
  “I would like people to clap and cheer for me for exhibiting no skill.”
  — Josh (16:45)

• On Running Into People in NYC:
  “I love the feeling of everybody's here. I feel very comforted by that.”
  — Josh (18:46)

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Important Timestamps

• 00:53 – Reflections on perpetual tiredness
• 01:02–03:25 – “Surprise Paul!” karaoke story
• 03:54 – Karaoke: the joy of being “percussion adjacent”
• 05:21 – Greta Gerwig Sacramento moment
• 06:56 – Missing Mel Brooks at the party
• 09:09–10:17 – Fame, recognition, and NYC nonchalance
• 12:07 – Online shopping compared to gambling
• 13:55 – The social fun of dice games
• 14:42 – Why craps is the best group casino game
• 16:45 – Hopes of applause without taking risks
• 18:46 – The comforting abundance of familiar faces in New York

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Conclusion

This episode of The Nightly offers a gentle, late-night meander through funny city encounters, the warmth of familiarity, and the sleepy delight of life’s small, shared joys. With cozy humor, Josh and Alison remind listeners that the best nights are often the ones spent laughing about nothing with friends—and that anyone, anywhere, could be “the most famous person at the bar” for the night.

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Transcript

[A]

Audio for sleep by hatch.

[B]

Hi. Good evening, everyone. I'm Josh.

[A]

And I'm Alison. Welcome to the nightly from Hatch, where your late night thoughts go to rest.

[B]

Alison, it's so nice to see you here again this summer. We've got lots of cool and exciting guests coming in to co host in the pillow fort and I'm so glad to be co hosting this week with my friend Alison Leiby.

[A]

I'm so happy too. We're here, we're doing it.

[B]

And it's nighttime.

[A]

It is nighttime. And I am sleepy.

[B]

Me too. Always being sleepy, though, doesn't really tell me what time of day it is.

[A]

No, it could be any time of day. And I'm like, I could go to bed.

[B]

Yeah, for sure. I haven't told you this yet, but the other night my wife Maris and I were out celebrating our anniversary and we were just finishing up dinner and a man walks by and Maris was like, paul? And he didn't answer. So I was like, oh, that does look like Paul. I just saw the back of his head. And I texted Paul, are you at this restaurant? And he doesn't live in the same city, he lives in Philadelphia. And so I texted him like, are you in this restaurant in New York? And he was like, are you? And I was like, that would be a ridiculous thing for me to ask if I was not also there.

[A]

That's kind of the whole premise of the question is, I'm here, are you?

[B]

I'm here, are you?

[A]

Right.

[B]

Again, very strange to receive a text like, are you there? Are you? No, I'm like, I'm at the Louvre. I just was wondering if you were hanging out in my neighborhood. And he was there. This is our mutual friend Paul of the musical comedy duo Paul and Storm, who we did one hour of karaoke with

[A]

one deranged, panicked hour of karaoke. Of sober karaoke.

[B]

Yes. And it was so fun. And the two of us, I would say, sang maybe as badly as we've ever or anyone has ever sung.

[A]

Top, I'd say top five worst performances.

[B]

Certainly one of the worst performances of my life. Oh. So he was there with Storm of his musical comedy duo and Jonathan Coulton, the singer, songwriter, and Drew, who was. That's kind of the four person core of this planning committee and host committee for the Joco Cruise, Jonathan Coulton's week long cruise that he is kind of the host and they're the curators of. And so they were having dinner after a meeting and they, Paul was like, you busted me. We had ordered you two Shirley Temples on us.

[A]

That's fun. That's fun.

[B]

And so the Shirley temples came like 10 minutes later, and then we went to look at them. And they had all clearly been watching us for when the Shirley Temples would land because they all did like a four person unison cheers from across the room.

[A]

That's so fun.

[B]

That's fun. And we have talked so much about karaoke, but we were really ripping it up the other night too. You and I and Maris and Lindsay and Hannah.

[A]

Yeah. Just getting ripping.

[B]

You were doing a lot of kind of song adjacent.

[A]

Screaming was like some of those sounds hit and you're like, I just want to make that sound.

[B]

Yeah, yeah, yeah. You were just kind of adding it as texture to the room. Oh, yeah. I mean, that's a classic.

[A]

That's a classic for a reason. It's so great because I just know I can't sing well. So I'm like, what else can I provide here as kind of being like percussion adjacent or something?

[B]

But you sound good. You do Cher, which you didn't do this time.

[A]

Oh, yeah. I can do Cher. Cause she has like a nice low registers. I have a low voice.

[B]

Yeah.

[A]

A great karaoke time was had by all.

[B]

I know. Well, there are only five of us in the private room, so we all got to sing a lot.

[A]

I think that's like the key is like a small group. I went and did it with three people. Like, there were three of us total like a month or so ago. And three was a kind of magic number for like, we were just doing like a everybody. It was just like alternating every other person, which was a dream.

[B]

Wait, was. I think I was there that night. I had to. Went home early.

[A]

Yes. Yeah.

[B]

Was that the night of. It was Zara's book launch.

[A]

Yeah. Zara's book launch. Or like one of her book events.

[B]

Yeah, she had many book events, but it was really great event. Wait, can I say something from that night?

[A]

Yes.

[B]

We were at this book event in Brooklyn and there was like, everyone had kind of congregated so that Zara could say just a few words about the book. It was really lovely. And Maris kind of nudged me and was like, I think that's Greta Gerwig right in front of you. The director of Barbie, of course, and Little Women and Lady Bird and whatever. We all know who Greta Gerwig is. And Zara was talking about, like, California. And then Greta Gerwig just like chimed in really genuinely and enthusiastically like, yeah, Sacramento. And I was like, that's definitely. Like, if I were Trying to write a line of dialogue that would signal to the room that the person you think is Greta Gerwig is actually Greta Gerwig. She would bring up Sacramento.

[A]

Yes. She was so lovely. It was such a fun, so cool. I love a New York moment where you're just like, you're in a tiny space doing something with mostly people, you know, but then like, there are casually, like celebrities and, you know, very cool people also there doing the same thing in the same tiny space.

[B]

Who is your number one? Like, I can't believe this person is at this party. I'm also at.

[A]

Ooh, I have to think for a second about that. Do you have one in mind?

[B]

I do have one in mind.

[A]

What is yours? While I trigger my brain to remember anything ever.

[B]

I don't think I've told this story on the nightly before, but many years ago I was at a pre Emmys party. I used to write for the show last week Tonight hosted by John Oliver. And we were nominated for an Emmy and we were at this HBO party before and I left early. I was like, we're in Los Angeles. I'll go do this show and then I'll meet up with everybody later. And after I left. So this is slightly different, but after I left, I found out that Mel Brooks had come to the party and my friend Scott got to talk to him and it's like truly a number one, top of the heap. Most jealous I've ever been of anyone for any reason.

[A]

Yeah, absolutely. When it's like a legend level person in the industry, you're just like, yeah, I want to have that. Greta was one of the more recent actual. Oh, I'm at a party with a famous person and we're both friends with the person throwing the party.

[B]

Well, it's also, I'm always very impressed to see a person of that stature and ease of recognition to move with such a low footprint. She seemed to just be outside.

[A]

Yeah, she's like, this is not supposed to sound. It's just like she's like another woman in Brooklyn.

[B]

Yeah. I always have a lot of admiration for a famous person who rolls with no entourage.

[A]

Yes, me too. Because it's just trust where you are and the people around you enough for everybody to be normal. Which is a nice thing that I feel like creates then more of a safety of, oh, nobody's gonna bother me. I feel like if you have that

[B]

energy, yeah, people feel more at ease. But I bet there's. I wonder who the threshold who the person on the cusp of, oh, I just can't live like that. I need a guy with me at all times to be like, no, thank you. Like, I bet, like, Charlie Puth needs a body man.

[A]

Yeah. Though I wouldn't recognize him if you put him in front of me and were like, this is Charlie Puth. I'd be like, who?

[B]

Charlie Hooth.

[A]

Charlie Tooth. He's a dentist.

[B]

Which is interesting because Charlie Bucket wasn't a bucket. He was a child turned candy muggle.

[A]

It's crazy that he wasn't a bucket.

[B]

I know. Do you think when he took over the factory, he changed the name of it to, like, Bucket?

[A]

Candy Buckets. Buckets. Bucket is a really funny word.

[B]

It's a really funny name.

[A]

I was at Italian restaurant Carroll Gardens, and it was, like, very fun. This is a very stupid, like, a thing that, like, happens for us, that it feels nice. But then, like, when you tell the story, people are like, you suck.

[B]

People. You tell us people. Just your face, like, you suck.

[A]

We were. I was. I was with Zara. Friend, author, brilliant chef, and we were just, like, having a drink at the bar. And like, a couple recognized me, like, as a person. Like a. Like, not as somebody they know, but like a. A public figure comedy person. And then Eben Moss. I always forget his last name.

[B]

I always want to say Bacharach, but I.

[A]

Me too.

[B]

I don't think that's quite it.

[A]

Yeah, but fantastic actor. Also a neighborhood guy. Rolled in with two friends and no one bothered him. And then also when I was leaving, another table was like, oh, my God, we love your show. We come every Monday. I was just like, oh, I'm getting recognized more than the famous person in this particular establishment.

[B]

You're like, thank you. And they're like, no, no, no. We meant the Bear. We love the Bear.

[A]

Yeah, we watch it every Monday. But it's like, obviously, there's also the level of people being like, I can talk to you because you're not that famous.

[B]

Yeah, that's totally true.

[A]

For people not bothering him because he is, is my assumption.

[B]

I think I get recognized the most at concerts with good lighting, which the good lighting just helps. But there's this venue that is really wonderful outdoor venue called Pier 17. Which you've been to. Yeah.

[A]

Yes.

[B]

And it's like, right on the waterfront, and you can see the Brooklyn and Manhattan Bridge from where you watch a concert. It's like, in the background of the stage. It's so beautiful.

[A]

It's so beautiful.

[B]

And they mostly do shows late spring through early fall, so it stays light. Pretty laid out. So we got to the concert and it's fully light out. It feels kind of like if a festival weren't a nightmare to attend. And I feel like I often get recognized there because of a common interest in the same kind of music and then the quality of lighting. And then two people posted online or sent me a DM that were.1 person said, I saw you. Didn't want to bother you. Just want to say, I'm a fan. Very nice. Really sweet. Someone did say hello, which is very nice as well. And then someone posted on some social media network, I think. Bluesky, you had mentioned you were going to be at the show. I was gonna try to say Hi, but, like, 60% of the guys there look exactly like you.

[A]

Yeah, I mean, you and I both kind of have looks that, like, really fit in with the audience, which we've fostered. Like, I have been recognized at the Rachel Comey sample sale. Like, everybody there was me. Like, it was like, just a bunch of Brooklyn gals trying to buy weird pants at a deep discount.

[B]

Hey, I think that that's an important part of the story, too.

[A]

It's like, if you're gonna see me, and you're like, is that her? It's like, it probably is if you're there.

[B]

Maris has been. I just realized that she wore a beautiful dress out for our anniversary, and it was brand new, and she'd got it, like, steeply on sale. I think it was from anthropology. And it was like, final sale, no returns. And I did realize that ordering a garment like that that you're not sure is going to fit right on Final sale, no returns. It returns. Returns. Final sale, no returns is like her version of online gambling.

[A]

Yes, yes. Yes, it is. Yes, 100%. I share that with her. Like, I'm going to buy a dress that I know isn't my size, and I'm not going to be able to return it. And I'm going to hope I can make this kind of work out because I want it.

[B]

Would you? Because I'm. I don't do online gambling. I've occasionally done, like, a little light slot machining or whatever at a casino.

[A]

Yeah, yeah, yeah.

[B]

I do kind of like to, like, make a wager.

[A]

Yes.

[B]

Like, around the world in 80 days style.

[A]

Yes, yes, of course. Yeah. Something that really relies on everybody doing something intense. Yeah, I do a little. I have, like, some friends who have recently gotten into playing, like, dice. Like, games with dice, which I like. At first I was like, ugh, I hate games. And then I Was like, I like this one. This is fun. It's, like, easy and doesn't require a lot of skill because it's chance. You're rolling dice and seeing what happens. And there's like, some light gambling that goes on within that in that I find that fun because we're dealing with single dollar antes and like. And just kind of like, all right, we play a couple rounds, I spend five bucks. Maybe I make some money. Maybe I, like, I just don't love the financial risk of gambling. But I'm like, oh, I've spent, you know, way more on way less. It just puts some stakes into, like, a game that otherwise has, like, no stakes.

[B]

Right. Because, like, roll. If you roll dice and there's no added drama to it, it's like, oh, eight. You're like, who cares?

[A]

Right. It's like rolling dice is like part of another game.

[B]

Right, right, right, right. Exactly. It's. Exactly.

[A]

It's like, that's how you can do stuff. It's just like, the mechanism to keep a game going. So if that's all you're playing. But it's very fun.

[B]

I would like to learn how to play craps. And I say that knowing that whenever someone has tried to teach me, my body has rejected it. Like, the wrong blood type.

[A]

My eyes go black.

[B]

Yeah. Truly. I wake up like, an hour and a half later just foaming at the mouth. Sorry. Someone tried to teach me how to

[A]

play crabs holding the stick they use

[B]

to gather all the, like, gnawing on it. Like, we put it under your tongue. My friend Dan, who I've known since I was, like, 8 years old, is a. Not an evangelist. Is too strong, but he is like a craps enthusiastic in that it is a casino game where instead of being mad at the people around you or trying to win money from them, everybody kind of gets in the inner groove together and cheers for each other. Because everyone's. From what I understand, everyone's winning is contingent on the person rolling.

[A]

Yeah. Which I do enjoy. That kind of sense of, like, group game versus competitive or just like, I'm in this alone. I think what makes gambling feel so unappealing to me is, like, that you're in it kind of alone.

[B]

Yeah.

[A]

Instead of, like, you've got a team or a group. That's why craps is, like, the only one that, like, I'm like, I wish I kind of understood this. And I know that I could. I'm smart enough to understand it. I just like, there is something about learning a game that I Just can't do.

[B]

Yep. You know, the other thing is you are allowed to bet against the person rolling. Like, you can bet for them to fail, but it's considered, like a kind of aggressive.

[A]

Well, yeah.

[B]

Which is so funny.

[A]

You're like shorting a craps table.

[B]

Exactly. That's the big short. It's just the big short. The little short.

[A]

Little short.

[B]

Craps. The little short. But it is like, I would just like to be the guy that rolls the dice and everyone's cheering for.

[A]

Yeah.

[B]

I don't even want to put money down.

[A]

Yeah. Though it is a lot of pressure.

[B]

But I think people generally understand that it's not your fault. Although if you did lose a bunch of people a lot of money, they would be like, give those dice to somebody else.

[A]

Yeah. Yeah. Right? Yeah. They're like, you don't get to do this anymore.

[B]

We know it's random, but we.

[A]

It's not because you're good or bad. It's just like, this isn't working.

[B]

We just think cosmically, this is wrong.

[A]

Yes.

[B]

Me saying that is like such a skeleton key, I think, to my whole personality of like, I don't want to make any risks. I would like people to clap and cheer for me for exhibiting no skill.

[A]

Yes. Yes. That is a very clear message of who you are and what you want.

[B]

Yeah. I just want to be kind of the center of attention in a way that has clear boundaries and that people are required to like the thing I do.

[A]

Yes. Yes. And that I lose nothing.

[B]

I lose nothing. And there's no chance I would lose anything. And I also don't even care about gaining anything.

[A]

Yeah. I can't think of another casino game that I would be interested in. I'm like, I get blackjack. I loosely could play a hand of poker and not need to be like, what do I do now? But I don't find them fun. Craps is fun.

[B]

I've had fun playing poker again at, like, a low stakes game at a friend's house.

[A]

Yeah. Yeah, yeah.

[B]

I've played a couple times at casino. Like, much, like, much younger. I was much younger. The game was roughly the same age, you know, like, statistically, yeah, it still exists, but I was very bad at it. And I don't. I don't get a thrill from it. I kept losing, and it really felt like the same emotional response I would feel if I just kept putting money into a parking meter. It was just like, oh, well, now my money's there. Well, I'm glad we settled that. And I was so I'm so glad to have had a forum to tell you about. Surprise, Paul.

[A]

Yes. Surprise, Paul. What a fun. What a fun Paul. Surprise.

[B]

Extremely fun. And like the four person cheers salute from like 20ft away. Like really, it was like a beautiful capstone to our anniversary night out.

[A]

Yeah, that's perfect. Such a, like New York. Like, oh, yeah, that's happened. Like everybody's here. Everybody's like.

[B]

I love the feeling of everybody's here. I feel very comforted by that.

[A]

I know that like at any point you could be like running into folks in like fun, weird contexts that like, I just never felt when I was living growing up in the suburbs.

[B]

Yeah, my parents run into people all the time and they'll tell me, but it'll be the parent of someone that I went to school with and I'm like, look, no offense, but I don't have that much of an attachment to this old person I met three times 25 years ago.

[A]

Yeah, my mom's always seeing people at Wegmans or seeing people, you know, CVS or whatever. And. Yeah, but I saw one of our friends at CVS the other day. So, you know, it happens here.

[B]

Okay. It could happen to anyone. Any. I think that's a beautiful lesson to take away from our conversation is you could see anyone at a CVS anytime, anytime. And I think with that it's a perfect time to say goodnight. Goodnight, Allison. And wherever you are, hopefully not right now in the same room as me. Good night to our friend Paul.

[A]

Yeah, good night, Josh. And good night to all the people who are great at craps and loving craps.

[B]

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