Sarah Silverman

Summary

Reclaiming with Monica Lewinsky: Episode Featuring Sarah Silverman

Introduction

In this engaging episode of Reclaiming with Monica Lewinsky, host Monica Lewinsky sits down with acclaimed comedian Sarah Silverman for an intimate and candid conversation. The episode, released on July 29, 2025, delves into their personal histories, the intricacies of stand-up comedy, navigating online interactions, and the broader theme of reclaiming lost or taken aspects of one's life.

Getting to Know Each Other

Monica and Sarah begin by reminiscing about their friendship and initial connection. Monica shares a humorous anecdote about mistakenly referring to Sarah as "Sarah Silverman with the last name," highlighting the natural camaraderie between them.

• Monica Lewinsky [01:57]: "We went to lunch and I had such a good time with you. Like immediately felt like Mish Booka."
• Sarah Silverman [01:50]: "I missed the boat."

Their light-hearted exchange sets a comfortable tone for the conversation, emphasizing their mutual respect and affection.

Personal Struggles and Overcoming

The discussion shifts to personal challenges they've faced, starting with Monica's experience of surviving a global scandal at 24 and Sarah's struggles during her youth.

• Monica Lewinsky [15:35]: "First of all, I think it's amazing that you talk about it because you can't be the only person in the world to whom that's happened."
• Sarah Silverman [16:07]: "I feel like anyone can hear that, even the most self-deprecating person and be like, I did. Yeah, I did. And that's a great thing."

Sarah shares her experiences with being a bedwetter until she was 15 and not getting her period until almost 18, which contributed to her resilience and fearless persona in her comedy career.

Stand-Up Comedy Crafting

A significant portion of the episode delves into Sarah's journey in stand-up comedy. She discusses the process of developing new material, the influence of veteran comedians like Chris Rock, and the importance of embracing failure as a stepping stone to growth.

• Sarah Silverman [30:57]: "I never really think about it. I just start. I just go, you know."
• Monica Lewinsky [33:49]: "So how did you learn to trust that? Or did you always trust it?"

Sarah emphasizes the necessity of performing live to refine her comedy, acknowledging that bombing on stage is an essential part of the creative process.

Online Interactions and Bullying

Monica and Sarah explore the complexities of online interactions, particularly focusing on instances where Sarah transformed negative encounters into meaningful connections. Sarah recounts how she engaged with critics, revealing their personal struggles and fostering unexpected relationships.

• Sarah Silverman [09:25]: "There was a guy who just called me the C word on something... and we became kind of pen pals."
• Monica Lewinsky [10:38]: "That became a really big story... an incredible example of ways that you can turn a situation around online."

This segment highlights the potential for empathy and positive change even in seemingly hostile online environments.

Reclaiming and Personal Growth

The theme of reclaiming—recovering what has been lost or taken—is central to the episode. Both Monica and Sarah discuss their efforts to reclaim their narratives and personal joy amidst societal pressures and personal challenges.

• Sarah Silverman [46:13]: "I'm being very protective of my joy."
• Monica Lewinsky [48:07]: "Reclaiming is really elastic, you know, it's really elastic getting back something that was lost or taken from you."

Sarah touches on the importance of setting boundaries to protect her happiness, while Monica reflects on reclaiming her narrative through various personal anecdotes, including dealing with road rage and childhood experiences.

Navigating Relationships and Boundaries

The conversation also delves into maintaining personal boundaries within relationships. Sarah discusses the importance of protecting her alone time, especially after entering a committed relationship, and how she communicates her needs effectively.

• Sarah Silverman [46:18]: "I'm very protective of my free time."
• Monica Lewinsky [46:13]: "I think about that. It would be really hard for me to make a lot of adjustments..."

This exchange underscores the balance between personal autonomy and relationship dynamics, showcasing the need for self-care.

Humor and Coping Mechanisms

Throughout the episode, humor serves as a coping mechanism for both women. They share humorous takes on everyday annoyances, such as dealing with loud popcorn eaters at the movies, illustrating how laughter can be a tool for managing stress and frustration.

• Sarah Silverman [47:00]: "I just don't go to the movies anymore because of pop."
• Monica Lewinsky [47:53]: "It's all a part of reclaiming, exactly."

Conclusion

The episode concludes with reflections on community and mutual support. Both Monica and Sarah emphasize the necessity of taking care of one another and fostering connections as a means of reclaiming personal and collective well-being.

• Sarah Silverman [49:21]: "We have to take care of each other, and community's gonna be like the answer."
• Monica Lewinsky [49:21]: "Reclaiming is really about... getting your narrative back or just, you know..."

Their heartfelt discussion encapsulates the essence of reclaiming—rebuilding, healing, and rediscovering oneself through authentic connections and personal resilience.

Notable Quotes

1. Sarah Silverman [14:30]: "And it turns something so negative into something like where they get to be Mother Teresa."
2. Monica Lewinsky [06:04]: "If you have these somewhat seemingly irrational fears pop up... I hear something like that."
3. Sarah Silverman [20:57]: "I feel like anyone can hear that, even the most self-deprecating person..."
4. Monica Lewinsky [33:49]: "So how did you learn to trust that? Or did you always trust it?"

Final Thoughts

This episode of Reclaiming with Monica Lewinsky offers a profound exploration of personal growth, resilience, and the power of authentic connections. Through Sarah Silverman's humorous yet honest anecdotes, listeners gain insight into overcoming life's challenges and the ongoing journey of reclaiming one's narrative.

Transcript

[Monica Lewinsky]

Wondery subscribers can listen to Reclaiming with Monica Lewinsky early and ad free right now. Join Wondery plus in the Wondery app or on Apple Podcasts or you can listen for free wherever you get your podcasts.

[Sarah Silverman]

It immediately alleviates this rage they have towards me. It's like right away they're like, it's okay, don't worry about it. But they need to feel seen. They need to know that they were right and I was wrong. And I know that. And it turns something so negative into something like where they get to be Mother Teresa, where they get to go, you know, what you did wrong me, but it's okay. Hey, you're human.

[Monica Lewinsky]

Welcome to Reclaiming Sarah Silverman.

[Sarah Silverman]

Thank you, Monica Lewinsky.

[Monica Lewinsky]

I was. It's so funny. I was realizing as I was thinking about sitting down to chat that I actually, in my head and out loud, I always think of you and call you Sarah Silverman with the last name. I don't know why.

[Sarah Silverman]

A few friends have told me that.

[Monica Lewinsky]

Yeah, I mean, you're in my phone as Sarah Sullivan, but it's sort of just in case my phone got stolen. And I was thinking about, I think we first connected on Twitter and then became real life friends. And I just, we don't get to spend enough time together. But when I see you, it's, oh, I just love how you're able to kind of traverse the sort of the light and the humorous and the real in the deep and everything in between. And I had so much fun.

[Sarah Silverman]

We went to lunch and I had such a good time with you. Like immediately felt like Mish Booka.

[Monica Lewinsky]

Yeah, exactly.

[Sarah Silverman]

And you're telling me about. I think it's like an aunt. It's the story where it's like, yeah, he was in the Holocaust.

[Monica Lewinsky]

Big. Oh yeah, that was my sister in law. My sister. Oh my God. That was the. Still the funniest thing ever. Her mom and her uncle were having a conversation and her mom was like, oh yeah, he was in the Holocaust. Big time. Big time. My sister in law is an amazing writer and she's very funny. Actually, after we had lunch, my brother was already married, but I was like, you are not gonna believe who I had lunch with because you were his number one crush for a very long time. Celebrity crush. Oh my gosh. He likes funny women.

[Sarah Silverman]

I missed the boat.

[Monica Lewinsky]

Yeah. We could have his sisters in law. I mean, that would have been pretty good.

[Sarah Silverman]

That would have been great.

[Monica Lewinsky]

Yeah.

[Sarah Silverman]

So right. Feels so.

[Monica Lewinsky]

But I also tell this story about you all the time from. Cause you're such an amazing party thrower. And that pre Pandemic, I think the last party I went to of yours, pre Pandemic, where often you see these signs that say, you know, don't ask anyone for pictures. It was don't ask anyone to be on your podcast. And here we are.

[Sarah Silverman]

Yeah, but no, but I'm the worst, because, yeah, I have this one party usually once a year, and. And it's great. There's no one you're dreading talking to. It's like, all wonderful people. And I always made a big sign that said, no podcast solicitations. Cause it's like, you know when you're in a great conversation with someone and you're really. And then they're like, I'd love for you to come on my podcast. So you came. And a friend of mine who also is very like, wellness Crystals, was there, not immediately was like, oh, my God, you should do her podcast. And it was such a. I was such a hypocrite.

[Monica Lewinsky]

But it was. I was getting ready for us to chat, and it led me to. I had forgotten that you were part of the Crank Anchors team.

[Sarah Silverman]

Yes.

[Monica Lewinsky]

And so I got to thank you because I did this, like, amazing dive back into Crank Anchors that I had not listened to for a really long time. First of all, like, if anybody listening doesn't know, Crank Anchors was the. You would make calls and then you would play them with puppets, right?

[Sarah Silverman]

Yeah. They'd illustrate them with entire, like, incredible puppet master team, you know, like this. And. And there'd be a whole other layer of jokes, like visual jokes and everything. When we did it, it was. It was so fun, you know, And I just got involved because I was with Jimmy at the time, and Jimmy created it, and, like, just all the comedians in his orbit did it, and we would go to Vegas to do it, because I guess that's at the time, that's where you could record people without them knowing it legally.

[Monica Lewinsky]

Like, oh, the Linda Tripp episode.

[Sarah Silverman]

And by the way, the whole series, the Ryan Murphy.

[Monica Lewinsky]

Oh, Impeachment.

[Sarah Silverman]

Oh, my God. I was living off of that, and it was so great. I know you were one of the executive producers and.

[Monica Lewinsky]

Oh, I'm so glad. Yeah, it was really. I think it's so interesting. We seem to be in this kind of time in the world where we're revisiting different stories from a fresher perspective.

[Sarah Silverman]

I mean, talk about reclaiming.

[Monica Lewinsky]

Yeah. Yeah. And then I think it was the guy brought it up around Impeachment. You have a podcast and some Rando, like, called in and was saying something. Something about that when I had been on snl, he'd been. He was an intern.

[Sarah Silverman]

Yes, Right.

[Monica Lewinsky]

And then he had been tasked to go to my hotel room. Like, I was like, oh, I would never let anyone in my hotel. But then he was talking about that it was my. Basically my Filofax.

[Sarah Silverman]

You stole, like, a pen or you stole something from your room.

[Monica Lewinsky]

Which is so weird.

[Sarah Silverman]

And really thought that I was gonna be like, yeah, totally. Like, I was just like, that's not okay.

[Monica Lewinsky]

Yeah.

[Sarah Silverman]

Such a violation.

[Monica Lewinsky]

I think when I heard that, it totally validated for me that I had had what I thought of as an irrational panic. The first few years after 98, I was always pack all my undergarments in my carry on. Cause I was panicked about this idea if I lost my luggage that, like, my panties would be on ebay. And so, you know, and then you kind of, like every time, you know, whenever you have these kind of somewhat seemingly irrational fears pop up, and we all have them in different ways, and you try to talk yourself out of it of like, come on, now you're being. But I hear something like that, and.

[Sarah Silverman]

I think, well, I think as women especially, we're always saying, like, oh, this is. Just take it. It's this. You're being irrational. But especially you. You know, I mean, because you're. There's this, like, piece of history that is. You know, people want to. I can see people wanting a piece of it, but it's just like, everyone has moments. Like, I remember one time I was in an airport, a tiny airport in New Mexico, and for whatever reason, I was sobbing. I was. You know, it doesn't even matter, but I was sobbing. I had one tissue on me, and it was, like, drenched already. And I'm just trying to be, like, invisible. And this man and his son walk over, and they asked me for a picture.

[Monica Lewinsky]

Oh, my God.

[Sarah Silverman]

And I'm just like. You know, I feel them walking over, and I think maybe they're gonna offer me a tissue or put a hand on my shoulder or, you know, ask me if I'm okay. No, they want their thing for Instagram or, you know, it's just like.

[Monica Lewinsky]

It is wild. It's a weird. It's fascinating to me in some ways because I think it reflects this, like, thirst for connection in a way that people have. Like, it's a reflection of their own life in some sense of needing a connection or what do you.

[Sarah Silverman]

I love connecting with people, and there's such a difference between like fans that are fans that like, really connect with your material or they have some story that connects with me or whatever, and I love it, you know, but then there's the, like, the people with, like, the Disney bobblehead things, and they're just collecting those and they know I'm a Disney person, you know, a character, but it's. They don't have any connection to me personally. It's like they. It's like they're collecting baseball cards or something, you know, and they just, you know, and I. I'll sign it, whatever, but it's not like, you know, it doesn't feel like connection.

[Monica Lewinsky]

Well, I think that's what can be hard, is you're seen as a commodity in a way instead of as a person.

[Sarah Silverman]

Yeah. But I would say for the most part, when people approach me, it's just lovely.

[Monica Lewinsky]

I've actually talked about this story that I'm about to tell in some of the talks I've done because it was such an extraordinary moment where you really showed the world in many ways how positive things can happen on the Internet and social media. And it was a really touching story of. I mean, you can probably tell it better, but a guy who was kind of being a bit of a douche online, right?

[Sarah Silverman]

Yeah, There were a couple that. There was one guy who was very angry at me for playing Hitler on Conan, and very right wing Trump guy and very Jewish. And I engaged with him and I explained to him what Gallo's humor was. He's like, oh, yeah, I get it. Yeah, yeah. And like. And he oddly just very much went the other way into the very liberal world, which is not. I'm not trying to, you know, change anyone. I just engaged with him. I wasn't trying to, you know, groom him into a Democrat. Yeah, whatever. And then there was a guy who just called me the C word on something. I happened to see it, I mean, you know, and then I happened to click on his profile and I saw that he has, like, chronic back pain and all this stuff. And so when I responded, I go, boy, I know how mean that kind of chronic back pain can make you feel. Like, I get it. And we became kind of pen pals and direct message and we had a bit of a relationship.

[Monica Lewinsky]

But I remember that, like, that became a really big. No, it did. It became a really big story. And I think it was so impactful, at least in the, you know, kind of in the anti bullying space. People were talking about it a lot because it was an incredible example of ways that you can turn a situation around online, ways you can connect online, that the Internet can be used for good.

[Sarah Silverman]

I don't mean to like shine a light on the bullies as opposed to the victims of bullying, but of course, you know, bullies are bullied. They're hurt people. Hurt people. Hurt people, hurt people.

[Monica Lewinsky]

Exactly. But I think it was so important because it then I saw it as the knock on effect of what you did. I had an experience on my page where someone had said something shitty and someone else in my community had seen it and had gone to this person's page, had seen that his wife had recently passed away. And so she posted this thing. I saw that your wife passed away recently. I'm really sorry. You know, and that totally changed the interaction. I then saw it and that moment. And so I think it is. It's just, it's so important to remind people, I think as much as. As much as we can lash out online and can lash out in our lives, I think that sense of being able to.

[Sarah Silverman]

Or in traffic.

[Monica Lewinsky]

Yeah. Oh, well, I have road rage. I mean, I am a. I am a total. That is.

[Sarah Silverman]

Oh, my God. Monica.

[Monica Lewinsky]

I also realized I was watching the Knicks and Pacers the other night that I was like, oh, I have road rage when I watch basketball, like the game. I was like, Jesus fucking Christ.

[Sarah Silverman]

The fuck?

[Monica Lewinsky]

How did you, you know, like, having lived in New York, I'm a Knicks fan. So it was. But it is. That's where all my. That's where all my rage comes out. So do you not have road rage?

[Sarah Silverman]

I'm usually on the other end of road range because I'm maybe not the greatest driver, but I do have some because I know that energy is catchy. Yeah, negative energy is so catchy. When someone's mad at me on the road and they fucking pissed at me. You know, I take that on and then I'm probably pissed at the next person. Or if I'm late to something, I am much more apt to be like, fucking go.

[Monica Lewinsky]

Yes.

[Sarah Silverman]

And you know, so what? I tried to make adjustments. I leave very early for things.

[Monica Lewinsky]

Oh, good for you.

[Sarah Silverman]

You know, that eliminates a lot of road rage on my part when people are mad at me. I have a couple survival skills that are maybe not the most ethical things. But what I do is first of all, usually I fuck up, I did something wrong or whatever. And as they. This isn't, you know, I think this is good. As they pull to the side and I know they're about to unleash on me, I always Say so. You know, because I. It's usually something I did wrong. By the time they even meet eyes with me, I'm going like, I'm so sorry. Oh, you know, I'm like, I'm so sorry. And it immediately alleviates this rage they have towards me. It's like, right away they're like, it's okay. Don't worry about it. But they need to feel seen. They need to know that they were right and I was wrong. And I know that. And it's. It turns something so negative into something like where they get to be Mother Teresa, where they get to go, you know, what you did wrong me? But it's okay. Hey, you're human. You know, it's like this exchange. It's so fast. And then the devious thing I do is if someone's behind me and they're pissed at me for some reason, I really try to be free. Driver on the road, and they.

[Monica Lewinsky]

Or something, probably me one time, I.

[Sarah Silverman]

Will look at them in my rear view mirror, pretend to recognize them as a friend. I know. And go, oh, my God. Hi. And they're suddenly terrified that it's somebody they, you know, that they are doing this now to someone that they didn't realize they knew. And it's pretty great.

[Monica Lewinsky]

Yeah. No, it's funny because I will talk about my road rage in soft reclaiming of like, you know, their capital R reclaimings. Like getting your narrative back or just, you know, so many of the things. But then there are these small that for me, I consider it like a wid or reclaiming when I have called someone a fuckface. But I do not flip them off like that is I found my. I returned to my center. One thing we have in common, although not as long, was I was a bedwetter till I was about 8. And I also had a pacifier that I called my Saska until I was eight.

[Sarah Silverman]

Saska.

[Monica Lewinsky]

A Saska? Yep. And you like? It was interesting to me because you had better wedding issues for a long time. Right.

[Sarah Silverman]

Like, I think I stopped when I was about 15.

[Monica Lewinsky]

Okay. And no, it's. It's a. I think it is. First of all, I think it's amazing that you talk about it because you can't be the only person in the world to whom that's happened. And so I think it's. I don't think I talk about my bedwetting that publicly.

[Sarah Silverman]

So you're responsible, Monica. You could be helping people.

[Monica Lewinsky]

Exactly. But it's. So you also then started your standup kind of not that much longer after that. And so am I just trying to come up with crazy things, or do you feel like there was a connection in this? Because it seemed like 17, 16, 17 seemed young to start stand up.

[Sarah Silverman]

No, I think a lot of things converge. Well, I. I always wanted to be a comedian since I can remember.

[Monica Lewinsky]

Okay.

[Sarah Silverman]

And. And that's such a gift. Like, I. I just always knew, you know, you know, what I wanted. What I. You know, the plan is just, you know, and I think being a bedwetter until so late. And it must have had something to do with my actual, like, physical development, and not just emotionally, but, like, I didn't get my period until I was almost 18.

[Monica Lewinsky]

Wow. Oh, my God. I was 11.

[Sarah Silverman]

Oh, baby.

[Monica Lewinsky]

I know.

[Sarah Silverman]

Yeah. I mean, in a way, I was lucky. Other than my parents were very concerned and, like, take me to the doctor, and they'd just be like, I don't know. You know? I don't know. But I think I was just. I was really little for my age, and I just sprouted, like, at 17. And I remember when I got first got my period, I was like, 17 and a half. I was peeing. My friend. My high school friend, Lee Lambard, was in the bathroom, like, putting on makeup or something. We were like. I was in. We were in my mother's bathroom, and I was peeing, and I pulled down my pants, and I see blood, and I can't believe it's finally come, you know? And I go. And we were friends, but she didn't know. Like, I had a few very close friends that knew. I. You know.

[Monica Lewinsky]

Oh, okay.

[Sarah Silverman]

And so I go, I got my period. And she goes, oh, God, that's the worst. You know, But I was. And I, like, got up and went out to where my mom was, and I was like, I got my period. Aw. But it's.

[Monica Lewinsky]

I mean, did you read. Cause we're around the same age. So were you very into Are youe There, God? It's Me, Margaret. Yes, of course.

[Sarah Silverman]

But I was like, where's my.

[Monica Lewinsky]

Right. Yeah. No. And meanwhile, I was really early, which was pretty. Pretty torturous to be that.

[Sarah Silverman]

Yeah. I was so old. I was like, I put a tampon in on day one, you know? Yeah, it was like, you know.

[Monica Lewinsky]

But I developed early. And I remember there was a. It just felt. In grade school, it just felt like you didn't want to be the first. Right. So I wasn't the first one to get boobs. Thank God. I won't embarrass the girl whose name I Still remember same. Who was the first one to get boobs? But I, I remember it wasn't when I started developing, I was really self conscious about it because the popular girl hadn't gotten boobs yet. So it was sort of like until she got boobs it wasn't okay to have boobs. And then once she started to get boobs, then it was okay. So I mean it's just, it just feels, it feels bonkers. To look back on the kind of anxiety, I think I don't know if boys have it too, but particularly for girls, the kind of anxiety that we have around fitting in, you know, it's just, I mean that must have been, I'm thinking about that. That would have been stressful to not have your peer. I mean obviously if you didn't, if there were people you didn't tell. Right. Friends of yours that didn't know that, that feeling of like, you know, having to.

[Sarah Silverman]

Yeah. Cause we're like, something's wrong with me. You know, kids especially are always looking for where they fall, you know, and desperately desperate to be normal.

[Monica Lewinsky]

Right.

[Sarah Silverman]

You know, and, but in terms of the connect correction with stand up, you're asking like. Yeah, definitely. When I started stand up, I, to me, I, I, after being a bedwetter, I was just like, you know that he like the fear of humiliation was something that I was like a, I may have seemed fearless as a comic, but that's just because I was a bedroader for so many years. And like once you can overcome that, like that's a humiliation that, I mean it was a shame. I really never thought I would ever talk out loud about as a kid and as a teenager and of course, of course I do. And it's, I don't have any shame around it. I mean I was a kid, you know, there's that quote I keep seeing and it doesn't say who said it, but it's like you've grown into someone who would defend you as a kid and that's like that alone is everything. And I feel like anyone can hear that, even the most self deprecating person and be like, I did. Yeah, I did. And that's a great thing.

[Monica Lewinsky]

Yeah, it's interesting. I mean, I look back now on a lot of things in my youth and wonder kind of, I think in today's landscape or world we would see certain things as a sign that something was wrong. Might have been like, I remember steel. I stole the answer book to a workbook in second grade because I wanted to get all the right answers on the thing. And so. And then I also. I wasn't supposed to take my little recorder home and I did because I wanted to get better. And I look back and I think, okay, clearly I was going through something.

[Sarah Silverman]

Yeah, you're so scared you weren't good enough.

[Monica Lewinsky]

Yeah.

[Sarah Silverman]

Or even maybe the best.

[Monica Lewinsky]

And I do all this inner child. I don't. Do you do that. Yeah, all the inner child work and stuff and. But you do just sort of think. I just. You just want to hold them.

[Sarah Silverman]

I mean 100%. And that inner child stuff sounds so woo woo so la. It's like that's the only way there is a 10 year old inside of you. And when you lose your shit about something, that's the one losing her shit or his shit or their shit. If it's hysterical, it's historical. Is the.

[Monica Lewinsky]

Ooh, I have not heard that.

[Sarah Silverman]

Yeah, my shrink told me that.

[Monica Lewinsky]

Oh, that's a. That's a good one.

[Sarah Silverman]

And that's exactly it. It's like when you find yourself really losing it over something and maybe it doesn't feel proportionate, it does to you, but maybe to your partner or someone else it's like, Jesus, this is little you not being taken care of, not being hurt or something triggered from your childhood. You, you know, what are the things you weren't heard, you were ignored, you were, you know, not told. You were enough. You were not, you know, whatever it is your parents are gonna fuck up. You know, the best way they can raise you is to like be able to seek and afford therapy, you know, whatever. But like, you know, like my dad said to my sister who has all the kids in like, I'm a better parent than my parents, you'll be a better parent than me. And that's all you can hope for. You know. My sister Laura texted me a picture of me when I was little that I've never seen before. And I was like, that's her. That's the inner child I'm like fighting for and trying to continue to raise or re. Raise in a healthier way so that there's yeah, more space for others and.

[Monica Lewinsky]

You know, present time. Sarah, that's. Yeah, it's. Will you send that to me? I keep a. I have a folder on my phone of photos of people as a little kid and every once in a day it's like this started a long time ago, but about. It's like this idea from before you were broken and it sounds like that was.

[Sarah Silverman]

I find it heartbreaking but like in the Best way where I'm like, okay, you're who I'm fighting for.

[Monica Lewinsky]

Yeah.

[Sarah Silverman]

Cause I've got these like bags under my eyes. Cause I'm like, I didn't sleep much, you know.

[Monica Lewinsky]

And why, why did you not.

[Sarah Silverman]

I think I didn't want to wet the bed. I think I had a lot of stress. I just, I, you know, was watching late night television, late night talk shows.

[Monica Lewinsky]

Did little 10 year old Sarah Silverman have a sense since you wanted to be a comedian, did you just go, oh yeah, that's what I'm going to be, it's going to happen. Or did you hope and dream and not in the good Jewish way, not think it would happen?

[Sarah Silverman]

I mean, kind of both. In a very unthinking way. I just assumed this was my. Because I was funny. I was funny in my family. I was the funny one in my school. And that was always my place, you know, Like, I just always felt very like this is my identity. And I think of other comics that way. Like we're kind of an island of misfit toys, you know. And I like it. I love that, you know?

[Monica Lewinsky]

Yeah, yeah, yeah. No, especially because I think you bring so much joy to people. And I was watching your new special postmortem and there's a moment where, I don't know, the light shone on some portion of the audience where I saw someone. I assumed it was a woman, may not have been, but someone had their hand on the person next to them's back. And it made me think about how. I wonder if this special for you because you're talking about the loss of your dad and your stepmom in a short period of time and your mom who had passed earlier. But it made me think about if this will be a place for people to come in a way to grieve, to come and connect.

[Sarah Silverman]

I mean, I hope so because that's.

[Monica Lewinsky]

All I could assume was sort of that, that the person that I would just keep going with, she. Cause I think it was a woman, but the person that she was, she was consoling that person and that they had connected to something. Whether it was even, you know, in a funny way or maybe they had just lost someone. And so it just was really touching to me.

[Sarah Silverman]

So yeah, I really tried to make it not feel like. And not that there's anything wrong with a one person show, but I didn't want it to feel like a one person show. I wanted it to be comedy first. And I've always gone to the kind of darkest scariest corners of humanity for material. And this was very personal. But I was really surprised and pleased that people really connect to it in very personal ways. And, you know, a couple people suggested. And I thought about doing this for a while of showing pictures of my family as I talked about them and stuff. And I just really didn't want to do that. Cause I want people to picture their family and I want them to imagine. And. And then at the end in the credits, you kind of go, oh, there's. Oh, my God, the ekg, you know, whatever. The kind of Easter eggs in there. But I, you know, definitely saw during the tour occasional people bursting into tears, you know, and it isn't. I don't feel like the show is at all manipulative in that way, you know, and I really was. I worked hard on relief. Laughs and, you know, and not just like, oh, and poor me. And this. It's just. It's so universal and. But it. It was lovely. It became very cathartic for me. And I think it was also cathartic for a lot of people in the audience. I mean, everyone is on one side or the other of losing their parents.

[Monica Lewinsky]

I feel very lucky. I still have both my parents, so, yeah, it's. But I'm cognizant of, you know, things I think part of. I miss living in New York so much, but I, you know, aside from my niece and nephew that I'm obsessed with, that kind of keeps me here, I think the fact that my, you know, all the parent people in my life are aging.

[Sarah Silverman]

Yeah.

[Monica Lewinsky]

How did you decide sort of what you were going to put into this special? Because this was also, like, a lot more personal for you, Right?

[Sarah Silverman]

Definitely. I mean, it was. It was very honest and very vulnerable. But I didn't put a lot of thought. I didn't sit and decide to do it necessarily. My last special was for hbo, and as it was coming out, like, the month it was coming out, where I would do all the press like I'm doing now. My parents were dying, so I didn't do any press. You know, I. I was living in an apartment with them and my sisters and everyone. And when the special came out, I was at zero with. For new standup material, which is where I am now. You know, when I go out and do standup, I'm like, is this something? Is this something? You know, it's like you start over again. So when my parents died and I was. And when I first went back to doing standup again, I was at zero. So I had spoken at my dad's funeral. And, you know, his eulogy was very funny because I was recalling some classic schleppy stories. So that's where I kind of started from. I go, okay. I mean, when I'm starting over, I'm looking at everything I have is there. What have I not talked about? What do I have that's new? What do I. What could be something, maybe? And that was like, the tent pole. That was kind of the totem of, like, this is something. And I started there. And I remember getting to Largo, which is a club I work at a lot. And two of my sisters and I had just spent the whole day cleaning their apart, you know, cleaning out their apartment. And that was when my boyfriend Rory was like, boy, when it all comes down to it and your life is over, it's all about someone just cleaning out your Spanx drawer, You know, like. But just going straight from there to Largo and just talking. And, of course, that's just the most supportive crowd where they're. You know, you can't really tell if something works or not because the audience is like, basically like, go, girl. You know, you've got this. We love you. We love comedy. Oh, we see her trying, you know, but it's so supportive. It's a great place to kind of go and be like, is this something is. You know, and then you have to go to, like, the Comedy Store, the improv, to see if, like, people who are actually just, you know, not huge, huge, huge comedy fans of the whole process.

[Monica Lewinsky]

It sounds like you have to be able to really trust your instinct of, like, you were just saying, okay, oh, there's something here, or there's not something there. And sort of the fishing around is looking for something that kind of sticks, right? And so how did you learn to trust that? Or did you always trust it? And that was part of knowing you wanted to be a comedian? I think so, yeah.

[Sarah Silverman]

I don't know. I never really think about it. I just start. I just go, you know. I mean, you know, Flanagan, who runs Largolis, laughs at me because I'm. Every time I'm just like, I have nothing. I have nothing. You know, And I'm in a full panic backstage, and I'm just writing down, like, oh, anything, just. But that's where you have to start. You have to start there. And I really learned. I always say, like, I learned that a lot from Chris Rock of just. He'll do a special, and he does so much more prep than anyone else. I know he's like, oh, really? 200 shows on the road. 200 shows at, like, one club. You know, he just goes, goes, goes, goes, goes until it's all muscle memory. And he's really crafts, you know, and that's why he's so brilliant. And then he'll turn up at the Cellar at zero, you know, and of course, he's a surprise guest. Here's Chris Rock. The audience is out of, you know, it's only 100 people or so that fit in that room, you know, and the audience is out of their minds and they're so excited. And then he starts and he's just, you know, is this something, you know, maybe is this an area? And he is. It is brave. Not only is it totally essential to write comedy, you can't do it in front of your bathroom mirror. Like, you need the audience there. But to be brave enough to go, this crowd is so excited to see me. And I know I am going to disappoint them because I'm not doing bits I know work, I'm not doing anything I know works. I have to come here and try stuff and have it not go over, even though I'm Chris Rock, you know, and have it bomb or have it not work or have it be, you know, and maybe there's a germ of something that works and maybe there's, you know, and because a comedian becomes a comedian because they want strangers to like them, you know, it's not like the healthiest thing. It's really hard to get to the place of it really being a process that you respect and you go, I could kill with this material. This material, this material that's tried and true, but I will not grow that way. And my only choice if I'm going to continue in this career as comedian and be fresh and relevant, is to bomb and eat shit and slowly piece things together. And I'm going to disappoint this crowd. It goes against everything we need and want. Is brave.

[Monica Lewinsky]

Yeah. So, you know, I can't believe I didn't know any of that, that that's, like, how you work through material. And is there almost like an unspoken rule among audiences that if someone's working their material out in that sense, that they don't comment on it or on people for a bit?

[Sarah Silverman]

I feel like maybe, maybe whatever they want. I think for comedy fans, they love. They like seeing the process, they're into it, they understand it, but there's always got to be people that was like, I went to see Sarah Slytherin, she was terrible. You know, all she talked about was Call of Duty, which is like, all I'm talking about now. You know, it's like, you know, not so happy accident that my parents died right as I was starting new material. And it became this. This story. But this time I'm at zero. And all I'm doing with my free time is playing Call of Duty. I don't know who my audience is for this because, like, I'm in my 50s and I'm playing Call of Duty with, like, 14 year olds. And some people my age, it depends on the time of day you're playing. And. And it's so funny because I did 25 minutes at Largo last week, which I can't even believe I had that much new material, but I'm 24 of it. I'm hoping to displace with better material, you know? But, like, where I'm at is so funny because Rory wrote some joke about something he writes for Kimmel. And I go, oh, that's such an old reference. It was like. It wasn't even that old. But I go, I don't know, it's. I think it's like a little. If it's an older reference, it's kind of hacky or whatever. And then I was laughing because I looked down at, like, my stuff I was writing down to talk about. And it was a big gripe on the end of the movie Grease.

[Monica Lewinsky]

Oh, okay. Let's have it. I love Grease. I watched Grease probably, of course, so many times.

[Sarah Silverman]

We're the same age. Pretty. I'm a little older than you. It's like, of course, it was our whole world.

[Monica Lewinsky]

What's your gripe about the end of Grease?

[Sarah Silverman]

It was on, and I was watching at the end, and, you know, and she's like, sandy, you must start anew. Don't you know what you must do? And I'm just like, she's the one that has to change. The lovely girl who loves her boyfriend from the summer. She's gotta, like, wear slutty clothes, get a perm and start smoking. That's the happy ending. Not Danny Zuko to maybe just go like, hey, I should be vulnerable. And why am I ashamed of this awesome girl that likes me? I don't wanna act like I like her in front of duty. Like, what? This is the lesson we're learning. I mean, don't get me wrong, I love that outfit at the end.

[Monica Lewinsky]

Are you kidding me? Yeah, it's so funny. I just had a conversation for the POD with Sidney Crawford, and we were Talking about the exact outfit, you know, that outfit, the outfit at the end. But it's interesting. Cause I'm not sure I've thought about it this way, but that's pretty intense messaging for most of us Gen X women, of course.

[Sarah Silverman]

Right? It's crazy looking back, but we can still love it.

[Monica Lewinsky]

Of course we can still love it.

[Sarah Silverman]

It's like. Like I couldn't watch. When I'm on the road, I know I can always find a Friends or a Law and Order. And that's like my. Like your totem. Like, I feel like I'm home or Lotus Stone. And like, yeah, I love Friends. What's not to love about Friends? But it's all homophobic jokes. It's like 90% homophobic jokes. But we can know that and take that grain of salt and know that the world, part of the world, half of the world, has moved on past that and, you know, and. And still love it. Or Sex in the City, you know, it's. And the whiteness of it, the homophobic jokes, all those things. That's what art is. It changes with time. It changes from what you see from the perspective your world changing and the world around you changing. But it doesn't mean you have to throw it out. You just see it with a whole new perspective.

[Monica Lewinsky]

Well, I think that's one of the sort of complicated things about comedy and cancellation and all those things of just the. Where do you draw that line? Right. Comedy's always pushing a line, right? That's. I mean, otherwise we would do it ourselves. We wouldn't need it. I think we wouldn't need comedy. I mean, obviously we need to laugh. But I think part of where comedy comes from is sort of pushing a cultural line or a personal line in some ways. And so that sense of people being canceled for things they did in the past in a comedy routine, I don't know. It's complicated. It's really complicated.

[Sarah Silverman]

And listen, I've been on that side of it and I. But my view is you can say anything you want. Don't be ridiculous. Like the people. I can't say anything. No, you can say anything you want. And if you consider yourself an edgy comic or a comic right up to the line or passed it or whatever, the risk of that to be edgy is. There's risk. That's what makes it so cool. Right? Well, you're risking something, right? Oh, you don't like if you have any consequences to what you say. That's freedom of speech. Doesn't mean freedom of any Consequences. You're gonna lose people. You're gonna gain people to be so angry that there are consequences to. The things you say to me are so silly. And I've said a lot of things that I cringe at, things that I don't cringe at that people have been upset by, things that I go, whoa. My understanding of the world was very different then, and I feel differently now. And I've gotten so much shit for apologizing years later for a couple of things. And, you know, that's fine. People can get upset about it, but I feel fine about it. To me, it's so simple. I only apologize when I'm sorry. Yeah. And I never apologize when I'm not sorry, but I always apologize when I am sorry. And it takes nothing from me to do that to me. It is absolutely not a sign of weakness. I'm not doing it to prevent getting canceled. I'm doing it because I'm sorry you want to. I never apologize if I'm not sorry. And I hate when people are forced to apologize, even if I wish they would apologize. I think it's so stupid when people are made to apologize because it means nothing.

[Monica Lewinsky]

And also, I think those of us who are even remotely sensitive, people can feel and tell when you mean something, when you mean an apology, and when you did it because you had to.

[Sarah Silverman]

Yeah. Oh, you've never fucked up. You don't think you should apologize when you do? Yeah. Fuck you. It's fine then. Live your life that way. And don't be shocked when there are consequences to what you say and do.

[Monica Lewinsky]

Yeah. Roxane Gates calls it consequence culture, not cancel culture.

[Sarah Silverman]

Yes.

[Monica Lewinsky]

And it's such a great. Yeah. She's such an amazing.

[Sarah Silverman]

She's amazing.

[Monica Lewinsky]

It was funny. One of the other things, I mean, aside from, like, laughing my ass off watching your special, but one of the other things, I was laughing to myself. Cause I like to think I'm funny and I make myself laugh.

[Sarah Silverman]

You are funny. Thank you.

[Monica Lewinsky]

Sarah and Mike Lewinsky. Did you hear that? So was that. I too, learned what the Stranger is that you were saying. From the beginning, I had not heard that. And then I made myself laugh because I was like, oh, this is great. I have now learned about the Stranger from Sarah Silverman. And Miley Cyrus taught me what WAP was. So I was like, I've not heard. But that is. I did not know that. That giving a hand job with your non dominant hand called the Stranger. So.

[Sarah Silverman]

Masturbating. Masturbating.

[Monica Lewinsky]

Oh, okay.

[Sarah Silverman]

I love you. The Joke is when I say I jerk off my boyfriend. I've been taken to jerking off my boyfriend with my non dominant hand. Is a joke on that guys will do that so that it feels like someone else.

[Monica Lewinsky]

No, no, I get it.

[Sarah Silverman]

And when guys do that so it feels like someone else, that's called the stranger, which I did not know, but I love that. That's like, as if he feels differently when I use my left hand on him. Right. Although it would feel different because I just don't have the same command.

[Monica Lewinsky]

Yeah.

[Sarah Silverman]

Oh, boy. Lessons on lessons on lessons. We're at reclaiming with my exactly how.

[Monica Lewinsky]

To learn how to get the hand job. How is your family doing? How are your sisters? How are you guys all doing with all the loss and I mean, great.

[Sarah Silverman]

We're always remembering, you know, there's always a day or something. Oh, this is the day that. Or this is. You know, oh, this would have been. But we are in constant contact, which I love. I mean, I really love living in the future. Like, we're all. I have a sister in Israel. I have a sister in Australia, you know, and it's us four sisters, and our. My oldest sister, all of her kids, because she's the only one with kids. She has five kids. They're all grown. And so we do. We have a Silverman United WhatsApp chain, so we're always up each other's asses. And then we have a sister's chain, and we're constantly on that. And it's just so good to feel connected all the time. And then on Sundays, we don't always make it, or whoever can make it goes. But. But we have a. Just a family. Zoom, did you now, did you.

[Monica Lewinsky]

You don't have kids?

[Sarah Silverman]

I have no children.

[Monica Lewinsky]

Yeah. And so did you want children? Not want children.

[Sarah Silverman]

I always thought I would. I always assumed I would have kids. And then every time I. Once I was at the age that I could have kids and stuff, I was just like, oh, I don't have kids until I'm in my 30s. Oh, I'm not gonna have kids until I'm 40. I think in my 40s. You know what? When I'm 50, I'll adopt. You know, I get it. And I realized that I don't want kids. I love kids. I love kids. I'm baby crazy. All my friends have. You know, a lot of my friends have kids, and that's very satiating to me. But I, you know, I had a joke where I said this, but it's so really, really true, which Is I love kids. And the only thing I love more than kids is doing anything I want at all times. And I think as a woman, talk about reclaiming. That's important to me. I mean, listen, I'm not like every. Not in the short term. Everything I want to do, I do. But I like being the master of my domain. I like making decisions that support my own joy in this one life on this crazy planet in outer space, this dimension. I think that's my response. I feel like people, our biggest responsibility needs to be our happiness. Whether that's working to get food on our table and, you know, do all those things or, you know, saying no to things or, you know, like. And I. I know that now. People in my life think I'm always just blowing them off because I say this, but I usually am. I'm so busy, you know, like. So I. I'm very protective of my free time. So sometimes someone will invite me to something and I'll go, oh, shit, I can't. And usually it's because I can't, but sometimes it's not because I have something else scheduled. It's because I can't because I don't want to. And that's a reason. And I've been trying to get my boyfriend used to. He's so used to going like, well, I can't because I have to do this. And then we have to go here and no one cares, and it's none of their business. Just say, oh, fuck, I can't. Thank you so much for inviting me. And whether it's because we honestly can't, which is most of the time, or because we had plans to stay home and do nothing, or I did, you know, I've become very protective of that because I need. I need time alone. And now that I'm in a relationship, which I'm very grateful for, and I love spending my time with him, I have to schedule my time that's by myself, you know.

[Monica Lewinsky]

Yeah.

[Sarah Silverman]

And be really careful about it, you know.

[Monica Lewinsky]

No, I think. I think about that. It would be really hard for me to make a lot of adjustments to be with someone now who always wants to be together. Because I'm very used to sort of that same thing of doing what I want when I want to do it, having my time, having it be quiet when I want it to be quiet. I was at the movies on Friday night, and I almost snapped at someone who was chewing their popcorn too loudly. And I would. And they weren't in my group. Yeah, I, like, chop your popcorn Softer. I don't want to hear that. I mean, so. I mean, I don't quite have misophonia, but it's like the noises. The mouth noises. I notice that.

[Sarah Silverman]

That's misophonia.

[Monica Lewinsky]

Yeah.

[Sarah Silverman]

I mean, I just don't go to the movies anymore because of pop. If it's. There's a quiet moment and I'm hearing popcorn, I can't. I will get up and walk out and not stop walking until I'm home. It's like. And I know it's. It's popcorn, it's movies. You're allowed to do that. They're not doing anything wrong. But to me, it is so disgusting.

[Monica Lewinsky]

Yes, they are.

[Sarah Silverman]

I eat popcorn. Right. Keep your mouth closed.

[Monica Lewinsky]

Right. No, it's.

[Sarah Silverman]

A Whole other people exist.

[Monica Lewinsky]

It's.

[Sarah Silverman]

I mean, I always say, like, my biggest fear is someone eating an apple in a quiet car. I'll just open the door and, like, roll out.

[Monica Lewinsky]

Yeah. I usually end with asking people a question about if there's anything that you are currently working on reclaiming.

[Sarah Silverman]

Yeah, my time. I'm being very protective of my joy.

[Monica Lewinsky]

And important in today's.

[Sarah Silverman]

I need the men in my life to be angry for me. Like, for. Not for me personally.

[Monica Lewinsky]

Right. But.

[Sarah Silverman]

But what's going on for women in this country and for the LGBTQ community particularly, and black history being literally erased from schools. And this stuff makes me so angry, I wanna fight. And I'll lose. Cause I have no strength in my arms, but it makes me wanna punch. And I. I have been telling men in my life, especially white, straight men, like, I need you to get fucking angry or for. So that I can breathe. That's not much about reclaiming. I guess it is. It's adjacent.

[Monica Lewinsky]

No, it. It is because it's all for me. And part of why I was interested, you know, to have conversations around this is because it's. Reclaiming is really elastic, you know, it's really elastic getting back something that was lost or taken from you, you know, and there are all these steps that happen in there. And so this idea of somebody getting angry on women's behalf, men getting angry on women's behalf, because we have had something taken from us and we want it back. And that's what we're working on doing.

[Sarah Silverman]

I just think we live in a time where the. If there's a silver lining, it's that we have to realize that we have to take care of each other. You know, we have to take care of each other, and community's gonna be like the answer. I think in this current world, I don't know if we're gonna have another free and fair election. It's not certainly something I wanna spread. And when people go, of course there will be. I'm so happy. And I hope they're right. Right. But we gotta take care of each other. I feel like that's our purpose. That may not be your purpose, but I hope that it is, because we can't do it alone. I'm not crying. I'm just slowly losing my voice. Anyway, thank you so much for giving this.

[Monica Lewinsky]

I love you, too. I know. And I want to come and meet Rory, which. It is a hard name to say.

[Sarah Silverman]

Rory, Rory, Rory, Rory. You say fancy, it's easier. Rory.

[Monica Lewinsky]

Do you have any Grey Poupon?

[Sarah Silverman]

Rory.

[Monica Lewinsky]

Thank you so much for coming to do this. Yeah.

[Sarah Silverman]

I'm gonna pee now.

[Monica Lewinsky]

Okay. Go pee. Reclaiming with Monica Lewinsky is hosted and executive produced by me, Monica Lewinsky production Services by WTF Media Studios. Our theme song is by Ben Benjamin, and our music supervisor is Scott Velasquez. Our story producer is Elna Baker. And our senior producer, our managing producer is Megan Donis for Wondery. Eliza Mills is the development producer. Our managing producer is Taylor Sniffin. Nick Ryan is our senior managing producer. Senior producers are Candace Manriquez, Wren and Emily Feldbrake. And executive producers are Dave Easton, Erin o' Flaherty and Marshall Louie.