Sarah Silverman

Reclaiming with Monica Lewinsky

Prufrock LLC

Self-improvement, Society & Culture, Education

4.8 • 1.4K Ratings

🗓️ 29 July 2025

⏱️ 51 minutes

🔗️ Recording | iTunes | RSS

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Summary

This week on Reclaiming, we’re joined by the hilarious Sarah Silverman, whose career has been built on saying the unsayable—and making us laugh through the discomfort. In this intimate conversation, Sarah opens up about the quiet heartbreak of losing both her parents, the shame and humor of wetting the bed well into her teens, and the evolving landscape of comedy in a culture that’s constantly redefining its boundaries. With her signature blend of sharp intellect and raw honesty, she explores how pain shapes perspective and why vulnerability might just be the truest form of rebellion. It’s a candid, surprising, and deeply human episode with one of comedy’s most enduring provocateurs. And as a bonus, Monica makes another WAP-like discovery. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Transcript

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0:00.0	Wonderie Plus subscribers can listen to reclaiming with Monica Lewinsky early and ad-free right now.
0:06.3	Join Wonderly Plus in the Wondry app or on Apple Podcasts.
0:10.3	Or you can listen for free wherever you get your podcasts.
0:18.9	It immediately alleviates this rage they have towards me.
0:23.7	It's like right away, they're like, it's okay.
0:26.5	Don't worry about it.
0:27.3	But they need to feel seen.
0:28.9	They need to know that they were right and I was wrong and I know that.
0:33.2	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.
0:44.4	Welcome to reclaiming Sarah Silverman.
0:59.7	Thank you, Monica Lewinsky.
1:01.3	I was, it's so funny, I was realizing, as I was thinking about us sitting down to chat,
1:07.1	that I actually, in my head and out loud, I always think of you and call you Sarah
1:11.8	Silverman with the last name. I don't know why. A few friends have told me that. Yeah. I mean,
1:18.3	you're in my phone as Sarah S, but it's sort of just in case my phone got stolen. I was thinking
1:26.6	about, I think we first connected on Twitter and then became real life
1:34.2	friends and I just we don't get to spend enough time together but when I see you it's oh I just
1:40.0	love how you're able to kind of traverse the sort of the light and the humorous and the real
1:46.8	and the deep and everything in between and I had so much fun. We went to lunch and I had such a
1:53.1	good time with you like immediately felt like Mish Buka. Yeah, exactly. You're telling me about I think
1:59.3	it's like an aunt.
2:06.7	It's the story we're here where it's like, yeah, he was in the Holocaust, big time. Oh, yeah, that was my sister-in-law.
	...

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