John Oliver

Reclaiming with Monica Lewinsky

Prufrock LLC

Self-improvement, Society & Culture, Education

4.8 • 1.4K Ratings

🗓️ 12 August 2025

⏱️ 72 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

This week on Reclaiming, we sit down with comedian, writer, and host John Oliver for a candid and thoughtful conversation about comedy, shame, and the power of laughter. John reflects on his interview with Monica in 2019 for Last Week Tonight and how that moment became part of her reclaiming journey. They explore the ethical tightrope of making jokes in a world full of gray areas and how humor can be both a coping tool and a way to call power to account. John shares what really surprised him about interviewing the Dalai Lama and the unexpected way His Holiness threw him off balance. With wit and depth, he and Monica dig into the weight of public shame, the risk of accountability, and why, for John, getting into trouble might just be the point. (And they use the C Word quite a bit!) 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

Click on a timestamp to play from that location

0:00.0	Wonderie Plus subscribers can listen to reclaiming with Monica Lewinsky early and ad free right now.
0:06.3	Join Wonderie Plus in the Wondry app or on Apple Podcasts.
0:10.3	Or you can listen for free wherever you get your podcasts.
0:19.1	I do like to get in trouble.
0:21.2	Yeah.
0:22.8	Oh my God.
0:23.9	I mean, that goodwoo, so I...
0:47.4	Are you woo-woo?
0:48.5	Yes, very.
0:50.0	Very, like I, you know, believe in different dimensions and the multiverse.
0:55.4	I'm like very, I just think that's all true.
0:58.9	Wait, Spider-Man multiverse.
1:01.2	Yeah.
1:01.9	Mm-hmm.
1:02.3	And it was also in everything everywhere all at once.
1:05.7	And then there was another movie, too, that they had it in.
1:10.7	And it's, I, that's like my spiritual belief that
1:13.7	there are all these different dimensions and we exist in different. Really? Yeah,
1:18.0	and our like energy and soul exist in different forms. You don't find that stressful at all?
1:23.4	No, I find it reassuring and interesting, actually. Really?
1:27.8	That is genuinely surprised me, because you've seen so good at understanding this dimension.
1:33.4	You don't think there's, really.
	...

Please login to see the full transcript.

Previous episode | Next episode

Disclaimer: The podcast and artwork embedded on this page are from Prufrock LLC, and are the property of its owner and not affiliated with or endorsed by Tapesearch.

Generated transcripts are the property of Prufrock LLC and are distributed freely under the Fair Use doctrine. Transcripts generated by Tapesearch are not guaranteed to be accurate.