John Oliver

Summary

Reclaiming with Monica Lewinsky: Episode Featuring John Oliver

Released on August 12, 2025

Introduction

In this engaging episode of Reclaiming with Monica Lewinsky, Monica sits down with acclaimed comedian and television host John Oliver. The conversation delves deep into themes of public shaming, the healing power of humor, personal resilience, and the complexities of navigating public life. Through candid exchanges and shared anecdotes, Monica and John explore what it means to reclaim one's narrative and find solace amidst adversity.

---

Reflecting on Past Collaborations and Public Shaming

The episode begins with Monica reminiscing about her previous interaction with John Oliver on his show, specifically referencing the Public Shaming episode from 2019.

• Monica Lewinsky [03:30]: "We first met in 2019 when I did an episode on Public Shaming. You invited me to be interviewed..."

• John Oliver [04:14]: "I remember you saying that. I appreciate that he kind of vouched for me in that way because the reputation before then was like, as a Daily Show correspondent, it's mean."

Monica shares her initial fear about appearing on John’s show, reassured by her brother who trusted John's respectful interview style. John acknowledges the shift in his approach from The Daily Show to more in-depth conversations on Last Week Tonight, highlighting his intent to explore topics rather than "get" something from his guests.

• John Oliver [04:15]: "I was just going to try and explore something."

The Role of Humor in Healing and Connection

A significant portion of the discussion centers on the use of humor as a coping mechanism. Both Monica and John emphasize how laughter serves as a vital tool in navigating personal and collective challenges.

• John Oliver [06:07]: "It's easier to be a bit of a dick, which I think I can be in comedy."

• Monica Lewinsky [07:12]: "I had this instinct that everybody has to laugh at some point early on because there's too much collective tension."

Monica recounts a moment from her TED Talk where she incorporated humor to alleviate tension, illustrating the importance of finding light amidst darkness. John shares his experience trying to make the Dalai Lama laugh during an interview, using humor to humanize and connect on a deeper level.

• John Oliver [26:43]: "The only way that conversation made any sense was when we were joking."

Navigating Personal Struggles Through Comedy

Both guests discuss their personal battles and how comedy has been instrumental in overcoming hardships. John opens up about the challenges of performing during the pandemic and how maintaining a weekly show provided structure and a sense of purpose.

• John Oliver [29:57]: "Having something that you had that had to be funny... was life-saving for me."

Monica shares her experiences with mental health struggles and the support she received from friends who used humor to lift her spirits. They highlight the therapeutic aspect of making others laugh as a way to reclaim one's own sense of self.

Cultural Differences and Personal Identity

The conversation shifts to cultural nuances, particularly Monica's experiences moving between the UK and the US. They explore the implicit social cues in British culture versus the explicit nature of American interactions.

• Monica Lewinsky [65:04]: "When someone says, 'you must stay for another drink,' it means you've overstayed your welcome."

• John Oliver [65:34]: "There are just incredible gradations of subtlety with British repression where you're supposed to try and find your way through it as an outsider."

John reflects on his dual citizenship journey, discussing the persistent anxiety related to his immigration status and the broader implications of American patriotism.

• John Oliver [58:38]: "There's a danger in thinking of yourself as the good guy all the time, because it doesn't reflect who you are as a country."

Humor in the Face of Tragedy

Monica and John delve into the delicate balance of using humor during tragic moments. John recalls the emotional challenge of making jokes at his grandfather's funeral and how laughter can keep memories of loved ones alive.

• John Oliver [43:48]: "The last thing he says to me is, 'You're an idiot.'"

• Monica Lewinsky [44:09]: "You can learn something interesting from everybody you meet."

They discuss how humor doesn't negate the gravity of situations but can coexist with sorrow, providing a means to process and remember.

The Ethics of Comedy and Social Responsibility

The duo touches on the ethical responsibilities that come with using comedy as a platform. John admits to sometimes crossing lines but emphasizes the importance of self-reflection and accountability in his comedic approach.

• John Oliver [11:18]: "I do think it is about being able to look yourself in the mirror."

• Monica Lewinsky [09:15]: "You had been willing to put yourself in the position where you would be under less control."

They critique instances where comedy intersects with social justice, highlighting the complexities of addressing sensitive topics without perpetuating harm.

Impact of Media and Public Platforms on Personal Lives

Monica and John discuss how media attention, especially during events like the pandemic, affects personal identities and mental health. John shares insights into how producing a show during isolation became a lifeline, while Monica relates it to her experiences of public scrutiny.

• John Oliver [32:06]: "Keeping the show going got that reductive. Once you've done that, then I think I realized that it's become healthy... as a coping mechanism for the world."

• Monica Lewinsky [31:06]: "Laughter is... the best medicine it can be."

Closing Reflections and Reclaiming Dignity

As the conversation winds down, Monica asks John about what he is working on reclaiming. John humorously declines, reflecting on the superficiality of reclaiming abstract concepts like dignity through comedy.

• John Oliver [71:21]: "I think I'd reclaim dignity, but I think I might have lost that above a pub in Mosley years ago."

Monica illustrates this with her own experiences of using humor to maintain connections, emphasizing the shared belief in the power of laughter to foster resilience and camaraderie.

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Conclusion

This episode of Reclaiming with Monica Lewinsky offers a heartfelt and insightful dialogue between Monica Lewinsky and John Oliver. Together, they navigate the intricate dance between humor and pain, public persona and private struggle, ultimately underscoring the significance of laughter as a tool for healing and connection. By sharing their personal journeys and professional experiences, Monica and John provide listeners with a nuanced understanding of what it means to reclaim one's narrative in a complex and often unforgiving world.

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Notable Quotes

• John Oliver [22:50]: "I do like to get in trouble. Good trouble."

• Monica Lewinsky [40:13]: "If you're not gonna do that, what's the alternative here?"

• John Oliver [56:42]: "Too soon is subjective. I'm not sure. Too soon to who, exactly?"

These poignant exchanges capture the essence of their conversation, highlighting the intersection of humor, responsibility, and personal growth.

Transcript

[Monica Lewinsky]

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

[John Oliver]

I do like to get in trouble.

[Monica Lewinsky]

Yeah. Oh my God.

[John Oliver]

I mean that good trouble, necessary trouble thing is the reason why that resonates so much is one it is good to make powerful people feel uncomfortable.

[Monica Lewinsky]

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[John Oliver]

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[Monica Lewinsky]

I'm very woo woo. So I.

[John Oliver]

Are you woo woo?

[Monica Lewinsky]

Yes. Very, very. Like I, you know, believe in different dimensions and the multiverse. I'm like very I just think that's all true.

[John Oliver]

Wait, Spider man multiverse.

[Monica Lewinsky]

Yeah. And it was also in everything, everywhere, all at once. And then there was another movie too that they had it in and it's I. That's like my spiritual belief that all these different dimensions and we exist in different.

[John Oliver]

Really?

[Monica Lewinsky]

Yeah. In our like energy and soul exist in different forms.

[John Oliver]

You don't find that stressful at all?

[Monica Lewinsky]

No, I find it reassuring and interesting actually.

[John Oliver]

Really? That is genuinely surprising because you've seemed so good at understanding this dimension. You don't think there's really.

[Monica Lewinsky]

I think this dimension is so hard. I think it's hard.

[John Oliver]

Oh, I'm not saying it's hard.

[Monica Lewinsky]

It's so hard to be a human being.

[John Oliver]

But you seem to understand it so well.

[Monica Lewinsky]

To me it feels more that there's an expansiveness that goes beyond just what's in front of us. This sort of linear, this horizontal experience here. And I think it's. Huh. It's more about the vertical and the spiritual and I mean, think about. Right. We only use 2% of our consciousness. Right.

[John Oliver]

It just makes me feel tense thinking.

[Monica Lewinsky]

Of it that way. John, welcome to Reclaiming.

[John Oliver]

It's great to be here. It's great to see you.

[Monica Lewinsky]

No, no, thank you so much. And the tables are turned.

[John Oliver]

I know. I don't love it, but it feels like the least I can do seeing you sitting with questions on your leg really feels like turnabouts.

[Monica Lewinsky]

Oh, yeah. Well, I tell everybody that it looks so thick, like there's so many. Cause it's in 18.5. Because I'm old, so I know I'm.

[John Oliver]

So much more comfortable in your position than I am in mine.

[Monica Lewinsky]

Well, I was thinking, you know, we first met. I think it was the first time we met was when I did in 2019. So last week, tonight did an episode on Public Shaming.

[John Oliver]

We did.

[Monica Lewinsky]

And you invited me to be interviewed. It took me only a year to say yes. Yeah, I was terrified, actually. It was my brother who really reassured me and he. Cause I loved your show. But he said, you know, if you go back and watch, John never takes the piss out of his guests. Like on the rare occasions that he interviews someone.

[John Oliver]

Yeah.

[Monica Lewinsky]

And so I appreciate.

[John Oliver]

I remember you saying that. I appreciate that he kind of vouched for me in that way because the reputation before then was like as a Daily show correspondent, it's mean. Right. It's often a. It's very reductive. You kind of turn to the sociopathic side of your brain because you're living in the edit the whole time. Whereas when we did the longer interviews on last Week Tonight, my whole relationship to conversations changed then so that I wasn't looking to get someone anymore. I was just going to try and explore something. And also, I haven't done many. You're one of the very, very few interviews that I've ever done.

[Monica Lewinsky]

Well, you did an amazing job. I mean, you did. You did know. And it was funny because I was thinking as I was picking up my outfit how. I don't know if you remember this. It was such a great moment when we were just about to start and my publicist of 10 years runs out and she's like, whispers in my ear, your Spanx are showing through your pants. And I had to go take my girdle off and it was like, come back. Okay, thank go.

[John Oliver]

What I remember is that I met you. Just remember you in Your office. Talk to me first. And of course, that's easier. Right. Because then we're just talking.

[Monica Lewinsky]

No cameras.

[John Oliver]

Yeah. It doesn't feel like there is a. There is something that you need to defend yourself against when that thing being a camera. And so I remember how fun it was to talk as human beings and then to watch. I knew how nervous you were, and it was. Aside from the Spanx aside, it was interesting seeing you put defenses up, those. Well, well constructed defenses. And it felt like as part of our conversation, I wanted to break some of those down. But that's not.

[Monica Lewinsky]

But you did.

[John Oliver]

Abrasive act.

[Monica Lewinsky]

But you didn't feel like you did. Didn't you feel like you did?

[John Oliver]

Definitely. But I also felt like it can feel predatory. Right. Trying to break someone's defenses down. Depends what you're trying to do it for.

[Monica Lewinsky]

Right, Right.

[John Oliver]

And it felt like when we laughed together, like that is an instant connection that actually does break down. So the moment that we were laughing, it felt like we were able to.

[Monica Lewinsky]

Yeah. It's interesting because I think when I did my TED Talk, I had this just sort of an instinct of like there has to. Everybody has to laugh at some point early on because there's just too much collective tension of. And I had been advised by a few people that they thought the joke I told because it was sort of connected to sex, to this young guy picking me up. And I just thought, I'm gonna go for it, because it's just. It was an organic moment when it actually happened, and I thought it's important. I brought this mug here. This is my mug. I know that I brought because I had a few mugs. You still have it?

[John Oliver]

I have this mug. I see this mug every day. This is behind. This is on my shelf behind me at work. I see this every morning.

[Monica Lewinsky]

Amazing. Yeah, but so I just loved. You know, in the interview you had asked me about had I ever thought about changing my name? And so then you revealed to me that your scandal name that you would change your name to was Alvin Oliver.

[John Oliver]

Yeah.

[Monica Lewinsky]

And if not Alvin, it would be Jax. Right.

[John Oliver]

So I can't. I can't even believe that I thought I could carry off the name Jax as a joke.

[Monica Lewinsky]

No, but you could.

[John Oliver]

I don't. That's really nice of you, but I don't think Jax is writing checks.

[Monica Lewinsky]

My personality can't catch Jax with a cks. But maybe not Jax. Right.

[John Oliver]

That is a really nice way of modulating that ambition. Yes.

[Monica Lewinsky]

Also, I was excited to sit and talk to you because I Wanted to thank you, too, because the episode really became a part of my reclaiming journey.

[John Oliver]

Oh, I'm glad.

[Monica Lewinsky]

So, you know, it was 2019, and my Vanity Fair essay had been 2014. And so it was like five years later, you have such a young audience that it was sort of this new crop of young people who I think either didn't know my name or only knew of me as the chick in the rap songs and didn't know my story.

[John Oliver]

Yes, that's right. But I will say I'm also very, very grateful that you did it, because I know that it was not an easy decision to make. It's as part of that process that you were clearly going through, like a TED Talk and a Vanity Fair op Ed is precise. Right. And it's all on your terms. You can get word to word, moment to moment. You can control all of it. And so I was extra grateful that you're willing to put yourself in the position where you would be under less control. And I do think it was a massive act of trust on your part. And I am very grateful that you thought we were worthy of that trust. Cause I know your trust had been.

[Monica Lewinsky]

Broken in the past, but you helped restore that.

[John Oliver]

All right. I'm really glad.

[Monica Lewinsky]

Yeah, no, thank you. It was great. And I appreciated that you acknowledged that there had been some times you had told jokes, too, which I think for me, it was really meaningful because I hadn't heard the jokes, thankfully. But whatever jokes, I have heard that when someone takes responsibility and apologizes, you actually end up like, sort of. It's not just back to neutral where you were. It's more positive because there's a value that I don't know if that makes sense.

[John Oliver]

Oh, it makes total sense. And I think I felt there was going to be more utility, especially in terms of an audience we were talking to, to be coming from a position where I was not unimpeachably clean. Right, right. And so it felt like there was a more interesting conversation to have because so few people are. Right. So you're not trying to talk from the high ground, especially in comedy. Right. Where even in the larger part of that piece, before even your interview came in, comedy can be a blunt instrument. And so the no bullying campaign that you were doing at that time was so kind. Comedy is often not kind. I think I might be inherently less kind than you are in some areas. So it almost felt like the shades of gray there. I guess I sometimes might end up being meaner in comedy than I would be as a human being. Even went back to look at it. And that's. We were using a couple of examples before we got to you about whether what was appropriate territory. That Olivia Jade thing gets really gray. Right. And I think the. Where a comedian and a human being falls might be different there. And so we were trying to take ownership with exactly where we were at that time. Looking back at it, I think I am still there, but I think it is completely reasonable to think, oh, no, I'm gonna fall on the human being side here.

[Monica Lewinsky]

Yeah.

[John Oliver]

And you're gonna sound right.

[Monica Lewinsky]

Well, you know, I executive produced a documentary that came out in 2021, and we were looking at exactly that. We examined a whole bunch of different stories where people had been publicly shamed. Everything from a guy who was driving home from work and had his hand out the window was making a sign that someone. I think it was like a might have been white supremacist. I don't even remember now. That's embarrassing. But, you know, it's just. I think those varying degrees. But the other part of it that I think feels always important to me is that we don't quite understand the human cost of the shamings and how long, you know, how long the tale can last. That, you know, the stories moved on, the headlines have moved on, and that person is still.

[John Oliver]

Yeah, yeah. But I think you're totally right. And even. Even the fact that, like, you find yourself going, I can't remember. I feel the same way about the Olivia J. Thing. Like, I'm struggling to remember all of those details. And I remember taking a position at the time that I thought it was going to be okay. I still think where I was under the moral code that I have as a comedian, which is going to be different.

[Monica Lewinsky]

Yeah. Yep.

[John Oliver]

Right. I think I can defend it now. I don't know if I can defend it successfully to everybody. Cause I think I probably can't. I think I can defend it to myself.

[Monica Lewinsky]

Right. And that, you know, I think ultimately it is about being able to look yourself in the mirror. But I think that I imagine it's a really hard thing to do actually, as a comedian of finding that line, you know, because if you meet the person, if you go into the human experience and you see someone for all their multitudes and, you know, you are totally right. Yeah.

[John Oliver]

It is much easier to be a bit of a dick, which I think I can be in comedy. If you don't personally know anyone. I don't go to many places or parties, as it happens. I don't. I'm Not a social butterfly in that way anyway. But it does feel helpful not to have friends in the world that you are criticizing.

[Monica Lewinsky]

Yeah.

[John Oliver]

And yeah, there's. To the extent to which you can. You just have to have some kind of internal barometer and hold yourself to it. And know with that example, the Olivia Jade example, I think I stand by it with others. And I can't think of any now because we do think about it, I might look back and go, yeah, oof, I think I've changed my mind on that.

[Monica Lewinsky]

Is it. Are there. You've said you don't have any examples that come to mind.

[John Oliver]

I'm sure there'll be ones I would look back on and wince. I can't think of any now. But that is definitely not to suggest they don't exist. I'm sure you could show me something. Go, oh, fuck, no, No, I wouldn't do that.

[Monica Lewinsky]

Yeah, totally.

[John Oliver]

I wouldn't do that now. And I wish I didn't do it then. We try and bake that in.

[Monica Lewinsky]

I think there were several examples. But then also, you were kind of my champion in court too, by calling out Jay Leno and making that amazing Dr. Seuss mashup. From the places you'll go. I think it was the places you can go fuck yourself.

[John Oliver]

Jay Leno.

[Monica Lewinsky]

Jay Leno by John Oliver.

[John Oliver]

Yeah, that's right. That's right. You were not involved in that. Yeah, no, I was pretty bad.

[Monica Lewinsky]

I would have been totally. I would have gone, let's make it bigger.

[John Oliver]

My particular problem at that time as well was that he had just been. If I'm remembering this right, he'd just been on TV calling for more civility in comedy. And I guess that goes back to a little bit what I was talking about, that it felt like, well, let's not pretend that we are blemishless here. Right?

[Monica Lewinsky]

Me too. I tell jokes too.

[John Oliver]

Everybody does. Right. It's just we all tell jokes privately. Right. I think we at the show probably spend more time than people might imagine thinking about how a joke sounds sometimes when we're just reading it out in the. Just to our staff, which is when we first say it out loud. Cause sometimes it's different out loud than on the page. Also, you can hear the kind of response that you get. The sound of a laugh sometimes recontextualizes a joke. So as when you're doing stand up, you're often like trying material. And sometimes you can think, oh, I'm not sure you took that joke the way that I was intended. That sounds a Little like the roar of the mob to me. I don't know if I like that. So you might calibrate the joke accordingly. So, yeah, to go back to Jay Leno, that I was also irritated that he had taken a moral position that week against the other late night shows. None of us are perfect, but I did not like being lectured by him.

[Monica Lewinsky]

No, no, I think neither did I. But, you know, I sort of now wear this as a badge of honor. There are only nine other people, some of whom are not around anymore who can say this. But, you know, when he finished his show, some. Some organization did some research and the top 10 targets of his, from the span of his show, I was number nine or 10, but I was the only person on there who had not chosen to become a public person. And so that's why when, for me, when you sort of called him out that way, it felt meaningful. It felt meaningful to me and to my family. You know, I mean, I of course didn't hear from him. But what is interesting to me is that, and I saw it so much in that episode and meeting you and being interviewed by you is how important social justice is. And I think I know just from the research, preparing to chat, that people sometimes mistakenly call you a journalist, which you push back against.

[John Oliver]

Not me. Yes.

[Monica Lewinsky]

Yeah. So do you think sometimes that maybe it's because, like, social justice is something we often think of for a journalist or an activist or maybe some good lawyers or something?

[John Oliver]

Maybe. I think, yeah, my relationship with that term is complicated because I think it's. I am not a journalist. The only reason I refute that is not to evade responsibility. It's that I just don't. I haven't earned that title. Right. That's not something that I am. I've not trained as a journalist. I've not worked as a journalist. I will say where it gets much grayer than the binary of this is and this isn't journalism is that we have a lot of journalists that work for us in our shows. So what we are doing collectively has a journalistic component almost all of the time, sometimes rarely, but not never. We engage in original journalism. Like just we have to do 30 shows a year. It would be impossible to do research these stories from scratch. So we are standing on top of other people's reporting most of the time. But there are occasional times when we will want to get an answer to something and it has not been answered yet. So we will go and try and find the answer to it, even if the question is who is making Death penalty drugs. That is something that one of our researchers took it upon himself to find out.

[Monica Lewinsky]

Yeah.

[John Oliver]

Didn't even tell us about it. He just. At the end of. In our end of the year meetings, he just said, I've been doing this thing. I don't know if we want to do this on our show, but I think I've found out where they're sourcing these lethal injection drugs. And if we're not going to do, I should probably give it to an outlet that's going to use it. So we did.

[Monica Lewinsky]

Wow.

[John Oliver]

But. So, yes, I have a complicated relationship with that. Only because we take all the responsibilities of journalism. It's just I personally am not it. I'm the unfortunate face of a lot of people's work.

[Monica Lewinsky]

Well, I think that that's really interesting. I hadn't seen the episode with the death penalty drugs.

[John Oliver]

Yeah. I mean, I don't know why anyone would.

[Monica Lewinsky]

Well, because. Well, no, because I think that's one of the things that's kind of magical about your show. Is that.

[John Oliver]

So fun. Sorry, go ahead.

[Monica Lewinsky]

Yeah. Especially in 2025. Such a good time.

[John Oliver]

Yeah, yeah.

[Monica Lewinsky]

Such a good time. But, you know, I just think that there is. I know they call it the John Oliver effect in terms of, I think, bringing attention to issues that then lead to activism and social change. Right. So I think people kind of come to your show and come to your perspective and the perspective of your team through you, however you want to say it. But I think it's driven by you. And people come and they're ready to hear something that they may have not thought about.

[John Oliver]

Yes, that I think is true. And we don't take that lightly at all. There's a reason that we don't say what our show is gonna be about that week beforehand. And it's normally because it's not like it's gonna drive viewers to it. It's not like anyone's gonna say, oh, I have to stay up, or be back home in time to watch 25 minutes on corn this Sunday night, or on lethal injection drugs or on, you know, mobile home financing.

[Monica Lewinsky]

Right.

[John Oliver]

It's. On its surface, it's often extremely boring and not something you might naturally be interested in. What we have found is that almost everything's interesting as soon as you start digging into it.

[Monica Lewinsky]

And, yeah, it's interesting. I feel like my mom sort of taught me, being raised that there's. You can learn something interesting from everybody you meet, you know, and so that. So I think that that makes sense in that way of that Curiosity that's there. It's interesting. But I mean, it was. That was happening early on because I think it. Wasn't it the fifth show? That was the FCC episode, right?

[John Oliver]

It might have been the fifth. Yeah.

[Monica Lewinsky]

I mean, that's like. That's a pretty. I know you had been on the Daily show, but that's a pretty, like, short Runway to get to a point where people are trusting and listening and actually fucking doing something.

[John Oliver]

Yes.

[Monica Lewinsky]

Right.

[John Oliver]

And actually, I think what we learned from that experience was not to ask people to do something that we didn't want them to do. Okay. I'm slightly blundered into it because like, you say, go to this website, people do, and it crashes and you think, oh, shit. Yeah, we might actually be operating with slightly more responsibility than is perhaps ideal. Right. It's nice to behave irresponsibly when you're a comedian and when you realize that you should not direct people's attention to something that you don't want attention on, that is worth thinking about in terms of your motivations and the consequences of it.

[Monica Lewinsky]

Are you really active on social media at all? Okay. Because, I mean, I think something I had to learn was you have to be really mindful if you clap back at people of just, you know, if you have a larger community or you have a public platform that even though they can, you know, really have fucking pissed you off and said something horrible, that it's just kind of the.

[John Oliver]

Yes.

[Monica Lewinsky]

You know, the punishment's not worth the crime. And so when. When you. When you can bring attention to something. Right.

[John Oliver]

So you're totally right. That is the same. I don't use social media in that way, but I definitely use the show in that way. And I probably make. I think you might be a better person than me there. I do think about it in terms of the clapbacks, but I do, you know, when making sure that, like, in that reductive sense of punching up, I do, like, do that. I do like to get in trouble.

[Monica Lewinsky]

Yeah. Oh, my God, that's an amazing quote. I do like to get in trouble.

[John Oliver]

I do when it comes to work. Good trouble. Yeah, that's right. Yeah, that's right. Strong John Lewis drop there. Yeah. I mean, that good trouble, necessary trouble thing is the reason why that resonates so much is one, it is good to make powerful people feel uncomfortable if you feel that they are over comfortable. And two, you can get away with more sometimes in comedy than you can without it, as you have found in terms of. Because you're funny and you have that ability to connect with an audience that way and to diffuse significant tension that way. It can be a blunt instrument, comedy, but it can also be a scalpel.

[Monica Lewinsky]

Yeah.

[John Oliver]

And I think we try and use it both ways.

[Monica Lewinsky]

Right. I mean, it's interesting for me. I like to think I was always funny, but I definitely 1998 sharpened my gallows humor, for sure.

[John Oliver]

No shit.

[Monica Lewinsky]

I mean, and my family. I think it's how we survived. And so that shaped my humor for me.

[John Oliver]

You know what you were thinking about? One of the only other people I've ever interviewed on you is the Dalai Lama.

[Monica Lewinsky]

Oh, well, you know, the Dalai Lama.

[John Oliver]

In me was the only reason I wanted to. Not the only reason, but the main reason I wanted to talk to him was that he's funny, which you would not think. No, no, but he's really funny. Likes. Com, and I'd read, really likes making people laugh. So I thought, oh, I think we might be able to have a conversation then. And that was in my head all the way through two flights to get to Dharamsala in India, and then a long drive up a mountain, and then you see more and more monks walking up the hill to see him. And I did start to get that sense of, oh, no, I've just flown around the world to fuck with this guy. I hope this is gonna be received.

[Monica Lewinsky]

Yeah.

[John Oliver]

In the way that I would like it to be received, because this could be real bad. And when he came, I remember that day, a group of people had walked from Tibet to come see him. And so he was late for the interview because he wanted to talk to all of them fair. And all they were saying was, please don't die. He can't even fathom the pressure he's under. I'm watching this happen, thinking, like, had a bunch of questions like this. I went out there. Oh, some of this feels like it's in questionable taste right now. But the first thing he did when he came in was he grabbed the sound guy's nose. He said, you got a big nose. Grabbed him like a parent. And then he looked at me and tickled me. And I think it's a little odd, but I think he was trying to do a little what we were talking about breaking down. Like people are treating him like a deity and he needs to get rid of that context to be able to have a conversation. I was still pretty nervous. It took me, like, 20 minutes to calm down. The first. We didn't use anything from the first.

[Monica Lewinsky]

Oh, really?

[John Oliver]

It was only when I made him laugh. That the whole thing seemed to actually make sense. But I was you.

[Monica Lewinsky]

Okay. So in that moment, did you start scrapping materials? Okay.

[John Oliver]

Yeah. Because it was. Oh, actually I can just. I can just make fun of you. He is a. This is going to sound very offensive. Right. But he is. It is a ridiculous figure. Like to it to be on the receiving end of that much worship is absurd for a human being.

[Monica Lewinsky]

Right.

[John Oliver]

You. One could argue. And so to be able to speak to him like two human beings, you have to kind of crack that.

[Monica Lewinsky]

Yeah.

[John Oliver]

And so only through making fun of him. Relatively off color jokes. I say relatively because I'm talking to the Dallai fucking llama. He may have sworn as well in his.

[Monica Lewinsky]

Did you keep that in.

[John Oliver]

I can't remember.

[Monica Lewinsky]

Okay.

[John Oliver]

But I'm do remember. Think. But it was the only. The only way that conversation made any sense was when we were joking and joking about hard things like how the Chinese government felt about him when he was going to die. Like dark things. But the only way to have that conversation in a way that felt like it was going to illuminate anything was gallows humor.

[Monica Lewinsky]

Yeah. Do you. It's interesting. Did he talk at all about that? He used. Uses humor to connect.

[John Oliver]

Not in that interview, but I had seen him talk about it in another one. Which is what. Where I thought if. I think I've got cover. Yeah, if that's how you feel.

[Monica Lewinsky]

Right.

[John Oliver]

We'll be fine. If it's not how you feel, it's something you said, we're in big fucking trouble.

[Monica Lewinsky]

Right, right, right.

[John Oliver]

I mean that's of course the intern.

[Monica Lewinsky]

Yeah. Did he. Did he say why he said yes?

[John Oliver]

I don't know why he said yes at all. But it was quite fun with him. It was. And it felt like the best way to tell the story that we were gonna tell to make him seem like a human being because he is a deity. Is.

[Monica Lewinsky]

I mean. Right, Right. I guess. Yes. But. But if he really were inhuman, then he wouldn't die.

[John Oliver]

Exactly.

[Monica Lewinsky]

So it's.

[John Oliver]

He is gonna die and the Chinese government really want that to happen. And that is both really dark and.

[Monica Lewinsky]

Yeah.

[John Oliver]

Darkly funny. Yeah. I don't think anyone had anyone else had made fun of him that day, so I think he was starving for it.

[Monica Lewinsky]

Yeah, exactly. Shoot me up with some humor, please. How do you. I mean like we're living in dark times now. How do you personally. Do you make yourself laugh? How do you, you know, do your kids ask hard questions about that?

[John Oliver]

I think those. The real. Those hard questions are probably coming. I Think they haven't been that hard yet, or so hard that it didn't feel like there was an answer that they'd understand at the other end of it. As they get a little older, it'll get tougher. I think, in terms of how I personally cope, I guess I'm very grateful to have the resource of the show so that we can find ways to put things into some kind of context, even if it is just for ourselves. Right. Even in really difficult weeks. There is a point to us turning up to work, even if it's to kind of explain things to each other. I think one of the many reasons I was very scared at the start of the pandemic was I was getting cut off from that. And I don't know how I'd have got through that pandemic as hard as it was keeping the show going.

[Monica Lewinsky]

Yeah.

[John Oliver]

Technically, physically getting it done, having to do it each week, having to kind of shape the experience of living in the world each week was, I think, kind of life saving for me in terms of. And having something that you had that had to be funny, however subjective that is, but that had to have laughter in it. And I was worried at times, especially because for the first time there was no. I couldn't hear any audience. Right. Just alone in a room. So it's hard to know, yeah. If you are actually connecting with people the way that laughter normally does. Right. And you know, as the. You're seeing the death count rise on cnn, like you do think, does anybody actually want this? So as it gradually became clear that something was connecting, it was a massive relief. Cause I don't know what I'd have done in a room on my own.

[Monica Lewinsky]

It's interesting, I've spoken to a few people on the show where I think this being a public person and your work, being connecting to so many, that during the pandemic was a real. I mean, obviously it was hard for everybody, but a real shift of. In self identity, of just that kind of question of, who am I if this doesn't ever come back? You know, but it's. I mean, I think what you did and SNL did, I think it was so important because the truth is, nobody was really looking out for our mental health. You know, everything was focused on our. No, but like, laughing is, you know, laughing really, you know, the cliche. It is the best medicine it can be. It can be the thing that brings you together, you know, it's. And to kind of. I think like you even release different chemicals and hormones and all sorts of other things in your body when you smile, when you laugh, you know, So, I mean, it is all of those things.

[John Oliver]

And I think for us, the most reductive thing was we just wanted to keep the staff paid, Right?

[Monica Lewinsky]

Yeah.

[John Oliver]

So it's like you gotta do a show. Whether that thing has any value, comedically or otherwise, it doesn't really matter. You just have to keep payroll going. It gets that reductive. Once you've done that, then I think I realized that it's become healthy or otherwise to such an extent, a coping mechanism for the world. If that had got taken away. Oh, boy.

[Monica Lewinsky]

Yeah. Well, I mean. And your show's been on HBO since 2014, right?

[John Oliver]

Yeah.

[Monica Lewinsky]

So, I mean. And they, like. Even during the pandemic, they just always kind of let you do your own thing.

[John Oliver]

Yeah. I mean, they didn't have any other television happening, so I guess we served a purpose there. It was not, you know, it didn't look like the prestige tv. It was just a guy in a white box. But, no, they stood by us. And I'm massively grateful and I hope that it was. I find quite hard to watch our show at all. But those. Those episodes I would not run back to watching. Not because I. I think that they were bad. More. That was hard.

[Monica Lewinsky]

Yeah. Yeah. Well, you know what? I had a talk that I was supposed to give early on in the pandemic, and so they had. Obviously, I couldn't travel and people couldn't come to do it, and so they'd come up with this thing of, you know, they'd, like, gotten a huge room and everybody social distanced. And I gave my talk to camera. So I understand that feeling of like, oh, has everybody fallen asleep? Or, you know, if. Just the moments of connection, you know, it's very hard if you are someone who connects in that way. You know, it's very hard.

[John Oliver]

You're just alone. There's something like. It would seem like sometimes, I hope my kids don't remember much about that because I was just going into an empty room ranting, talking to myself.

[Monica Lewinsky]

Yeah.

[John Oliver]

Now, technically, there was a camera there, but even then I was going nuts because it was that we didn't have our prompter hooked up to our prompter operator early on. So it was just a voice recognition software, and it was only properly calibrated with an American accent, so it couldn't. So it would freeze all the time. It couldn't understand. So I'd have to kind of have it enough in my head that I could read ahead and hoby catcher. It was so bad. And I. I. Through the eyes of a kid, I cannot imagine what they were thinking. That dad's going into that room to talk to himself for an hour and a half. Intimately swearing.

[Monica Lewinsky]

Fuck.

[John Oliver]

It's not working again. Fuck, fuck, fuck. And I tell them they can't swear.

[Monica Lewinsky]

Exactly. Exactly.

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[Monica Lewinsky]

Do you feel like if you look back, I know you were born in England and apparently played the viola. Is that. Do you still play it?

[John Oliver]

No.

[Monica Lewinsky]

Okay.

[John Oliver]

I absolutely don't play it. That was a miserable experience because I was so bad at it. And as I got better at it, I realized just how bad I was. So as I went kind of through all the grades, I think you have to grade eight. And the problem is when you start getting given real great pieces of music and you can't make it sound the way it is in your head. The disconnect. I found that beyond frustrating. The rage I used to feel.

[Monica Lewinsky]

Yeah.

[John Oliver]

Like trying to make it sound. And I would like. I remember there was a girl who was learning the violin with me. I remember she was called Emily Brown.

[Monica Lewinsky]

Hi, Emily.

[John Oliver]

Amazing violin player. And she had it in a way that I did not have it. We both nominally could do the same things with our fingers and bow. She made it sound so wildly different. So I hated it with a passion that I've not often felt for many other things. I wanted to smash it into a wall. Cause all it was was an embodiment of my limitations.

[Monica Lewinsky]

What's interesting to me about that too is that you have to have such great timing. Sense of timing to do comedy. And so that.

[John Oliver]

That's. Yeah, that's true. And I didn't. I couldn't get my body to do. I couldn't communicate through it. My head would know how to. I Know how this is supposed to sound. And I couldn't get my body to get the sound out of this thing. And the harder I worked, the further away it was clear that I was. And yet comedy I felt from when I first did it kind of had a weightless sense to it, even if you are. And it was also a way of coping with the world. Like what you were saying about, like, you and your family using it together. That feels probably monumentally true to me. Right. Like, I don't know how it becomes the only way to dig yourself out of a hole. Sometimes I find.

[Monica Lewinsky]

Yeah, yeah. No, I mean, did you have. I know sometimes it's like cliche about. Right. The comedians and the pain that they feel behind. I mean, did you have those kinds of experiences growing up or as an adult?

[John Oliver]

I guess the interesting thing is I use it to get through personal things. I tend to find comedy to be the only way or, like, interact joking around with people to be the only way to get through that stuff. However, the comedy I do professionally is not that personal. It's. I keep that.

[Monica Lewinsky]

Oh, that's interesting.

[John Oliver]

So you find a lot of standards who plunder themselves for material. I tend not to. To do that. Even though in moments of personal difficulty, comedy is almost the. And joking around is almost the only way to get through it with true gallows humor. But in, you know, neonatal intensive care, some places like it's you. You find those nurses can be really funny.

[Monica Lewinsky]

Yeah.

[John Oliver]

Because how are you not. Like, if you're not, how are you going to get through for days? I don't know. I actually genuinely don't know the answer. I don't know how people that are not compelled to joke around about dark things. I don't know how you get through the darkness.

[Monica Lewinsky]

Right. Yeah. I think I had had an experience where people really close to me, their firstborn son, had had a very difficult birth and was touch and go. And they were in the hospital for a while and had just come out and needed to do the bris. And I was like, bringing some stuff. So I brought one plate that had pigs in blankets and another plate that had just the little hot dogs. And I had a before and after sign in front of each. And I remember I thought it was so funny. I made myself laugh. And then I was walking in and I thought, God, I hope this is not a mistake, you know, because. Because there is that. That sense of darkness, you know?

[John Oliver]

Yeah. And I can understand, I think, theoretically, why someone might look at those two plates and think, why are you Doing this. What's wrong with you? My only instinct is, if you're not gonna do that, what's the alternative here?

[Monica Lewinsky]

Right. Yeah.

[John Oliver]

When things are this heavy, do you not want to find a way to lighten it? And I think some people don't. And maybe they're healthier. I don't know. I just. It is so antithetical to the way that I interact with life.

[Monica Lewinsky]

Well, and then also, do you think that that's. If I mean, some of this. I have a lot of British friends. I lived in the uk. I went to graduate school there. I have a very British sense of humor. So do you think of that comes from being British or.

[John Oliver]

It might being a man.

[Monica Lewinsky]

So, I mean, a man raised at a certain. Like, a man raised in a certain time, I think. You know, I don't know how you guys are raising your sons, but I think there's these younger generations. It's like they're being raised to explore their emotions, right?

[John Oliver]

Oh, I mean, definitely. And it's. That is very different. Like, I think. Yeah, you're totally right. Those are the two. Two really key ingredients there are being British and male. There's not really a lot of introspection historically and traditionally at that point of my childhood to that. Now, as I look back, there's probably reasons for that. Like, my parents were of a generation where their parents were in the Second World War. You're growing up being, I think, told not to talk. There wasn't, in my experience, not a lot of discussion about what had happened to them in that war. So there was. It was like, keep calm and carry on to a pathological extent. Yeah, right.

[Monica Lewinsky]

Yeah.

[John Oliver]

And there is a. There is a real argument for that during wartime. Right. But maybe once that war stopped, that keep calm and carry on things starts to get perhaps a little less.

[Monica Lewinsky]

Yeah.

[John Oliver]

Not so much of a good idea. So, yeah, I think absurdity and comedy was the only way I got through my childhood, the only way I'm currently getting through this phase of my life. And it's the only way I'll joke myself into the grave.

[Monica Lewinsky]

Right, Right.

[John Oliver]

I think I'm just practicing avoidance on a ludicrous scale.

[Monica Lewinsky]

And dissociation. I mean, we've all become like. We all have a PhD in dissociation now.

[John Oliver]

Although I do think, actually, you know what?

[Monica Lewinsky]

You.

[John Oliver]

I'm thinking of you, like, with those two plates, I. I found my granddad was really funny.

[Monica Lewinsky]

Okay.

[John Oliver]

And when he, like. And he was physically. He looked ridiculous. He kind of had bfg, like, ears. Massive ears. Looked ridiculous. Loved comedy. Was like a really sick, like, taught me how to misbehave as a kid. And I remember when he died, the last time I saw him was. He was in home. He was clearly dying. And my dad had left to get the car. And I climbed. He was on the ground floor, so I climbed out the window rather than say goodbye, like to walk through a hedge. And the last thing I remember him doing is chuckling to himself. And then he says, you're an idiot. That's the last thing he says to me. So I only say that in context for his funeral. It was not very funny for a long time, or felt like for too long. And it didn't feel to me like that was actually representing the person that he was. So I did a little speech then about his life, got some laughs, felt like it was going well. Probably got one or two too many laughs after that point. I remember looking at my mum's face with the kind of look of, that's enough now. Oh, come on.

[Monica Lewinsky]

Wait, how old are you at this point?

[John Oliver]

At this point? Oh, no, I was probably 21 or 20.

[Monica Lewinsky]

Okay, okay. So he. He had a really big influence in your life, your formative years. Yeah.

[John Oliver]

And it didn't feel like this was not, to me, to have no laughter in that room. And I get that it's sad, funerals, but laughter in funerals can sometimes be the thing that makes the memory of that person the most alive, in a way.

[Monica Lewinsky]

Yeah. No, I mean, I think I am my happiest when I'm laughing.

[John Oliver]

Yeah, me too.

[Monica Lewinsky]

And I think I can't. I just. I really can't abide people in my life who don't make me laugh. Like, it's just. You just kind of not worth my time. And the, you know, the inside jokes that you develop with friends over years and the ways that it is. I think 1998 was obviously hard, but then I had this, like, dark, dark decade. And my friend Anne, during that time, she was always doing lots of pranks and, you know, different things to make me laugh. I mean, she's that way anyway. But she had sent me this. She would send me funny videos when I was in really dark places, and I would get so fucking annoyed. Like, I don't want to look at this. You know, it was very offensive, like, to many people. Not to me, but. Or to her, but it was this video. It's so awful. I'm going to get canceled. But it's like bad women drivers.

[John Oliver]

Okay.

[Monica Lewinsky]

And there are all these bloopers of bad women. And it has this music of, like, Nair neigh. NER Nair. Ner. Nair neigher. And it's just this. And. But I would laugh, and when I would finish laughing. You can't go back to the point of how sad you were before. Right. So it's just, like. You just don't fall that dark in that moment. So in that moment, it shifts your resonance and your experience. And, you know, I just. It's so interesting because I think, like, I'm thinking about you being in your grandfather's room and that, like.

[John Oliver]

Yeah.

[Monica Lewinsky]

Was there. Do you think there was a part of you that thought, oh, it's funnier to actually leave through the window?

[John Oliver]

Definitely. I definitely. I thought it would make him laugh. I think I knew this might be the last time I was gonna see.

[Monica Lewinsky]

Yeah.

[John Oliver]

So you could probably analyze that two ways. One, that's spectacular level of avoidance of a real moment. I would argue that it was better that way.

[Monica Lewinsky]

Yeah.

[John Oliver]

Better to. Because, you know, who knows what you're feeling as an old man in that situation, knowing that your life is coming to a close, but, you know.

[Monica Lewinsky]

Or how many times you're laughing.

[John Oliver]

Yeah. To your point, if you get a laugh, if you laugh at your grandson who's being an idiot, call him an idiot and laugh. Maybe you're down to. You're not as low.

[Monica Lewinsky]

Yeah, maybe. Yeah. Yeah. No, it's. It's so interesting. And then I did not know that you went to Cambridge.

[John Oliver]

Yeah.

[Monica Lewinsky]

Smarty pants. Yeah. Like anybody who goes to the Oxbridge. Right.

[John Oliver]

I mean, I will say there are some monumental fools in that place. So. Yeah. I don't. I don't think it's necessarily anything. No, not really. No. I found that actually a little more difficult at the time, partly for a class. Classroom. We're riddled with class tensions in England. Utterly riddled with it. Right. And so the way I'd grown up in the school that I went to was not the kind of gilded passageway to Oxford and Cambridge the way that these private schools were. Yeah. And. Or just any of the kind of really nice private schools. It was a whole world I had not encountered much, so I hadn't met people like that. And so I was pretty uncomfortable for most of my time there. The only thing that I loved going back to what you were saying was that was doing comedy, was I found the Cambridge Footlights, which was a sketch group that famously, Monty Python came out of. Oh, my gosh.

[Monica Lewinsky]

I didn't know that.

[John Oliver]

Yeah. That.

[Monica Lewinsky]

Oh, my God.

[John Oliver]

And that was realizing.

[Monica Lewinsky]

Oh, Shit.

[John Oliver]

I think this is what I want to do with my life.

[Monica Lewinsky]

Okay.

[John Oliver]

I did. There was a friend of mine at the time, Richard Iowadi. He and I wrote a show together and I do remember of walking off stage after the first night and looking at him like both of us with wide eye and having that sense of, oh, no, I think I want to do this right.

[Monica Lewinsky]

Like a drug. Like a gateway drug.

[John Oliver]

Fully like a drug. I think like, this is going to take over my life. Let's hope it's.

[Monica Lewinsky]

Oh my gosh.

[John Oliver]

It works out well.

[Monica Lewinsky]

Yeah. And how did, like, were your parents okay with that or did they.

[John Oliver]

They were, to their credit. I think they were. I think they were. They never suggested that I stop.

[Monica Lewinsky]

Right. Okay.

[John Oliver]

Yeah. So.

[Monica Lewinsky]

So they had a lot of faith. That's really. That's pretty amazing because I think there are a lot of people who want to go into the arts whose parents just, you know, have a. Especially if you didn't. If you, if, you know, you're saying that you didn't come from this life of money. Right.

[John Oliver]

I remember my dad actually at one point saying this when I was making a living from it, when I admire the fact that you never gave up. And the crazy thing was it didn't even occur to me and it was odd hearing him say that. It was almost charting. Oh, so there were multiple points that you saw, like, you might want to pack this in now. And that just didn't. My head didn't go there.

[Monica Lewinsky]

I want to ask just quickly because I did not know that you had worked with Armando Iannucci. And I, you know, I don't know what it says about me that my two favorite political shows are the West Wing and the Thick of It.

[John Oliver]

So like, yeah, that's pretty much yin and yang, right, when it comes to representational politics.

[Monica Lewinsky]

So did. Did you feel like your. Was your humor at that time? Did that just fit in? People who like Americans. Right. Know him through veep. So.

[John Oliver]

Yes.

[Monica Lewinsky]

Right.

[John Oliver]

I've. Yeah. I actually found it was even before the Thick of It. I loved, I loved a show that he did called the Day to Day, which was an adaptation of a radio show on the hour that was about. That was a representative. It was like a news broadcast, but it was very, very. It was all fictitious, but it was done very straight faced. It was really good. And that watching that as a kid, I think I probably had a kind of reaction that you would have like to hearing a band that you love for the first time thinking, oh my God, I would tape it off. The tv, watch it again and again and again, the way you would listen to a song. So, yeah, he was a massive influence on me. And to the point that actually he actually. This connects a little to what we were just saying. I remember he did this show called Gash for. I think it was for one. One series on Channel 4. And it was just, I think it was like a post mid. Our version of midterm election, kind of. And he invited me to be on it. I remember at one point I made him laugh. I remember watching him laugh and it was a real laugh and thinking, oh, if I just made like my Jimi Hendrix laugh. Yeah, I think I'm good now. Like, I think. I think I'm playing with the house's money from here.

[Monica Lewinsky]

Okay.

[John Oliver]

Because if I've made that guy whose comedy was so important to me, if I can genuinely make him laugh.

[Monica Lewinsky]

Yeah.

[John Oliver]

I don't think I'm crazy to be doing this.

[Monica Lewinsky]

It's funny because that's how I felt when you laughed in our interview and then you said I was funny and I put it. It's in my, I think my Instagram bio.

[John Oliver]

Oh, really?

[Monica Lewinsky]

Uh huh. I have the quote, something about me being funny. John Oliver.

[John Oliver]

Yeah. I think.

[Monica Lewinsky]

Yeah, but it is. Yeah, no, that kind of humor. I think while I liked Veep, the thick of it for me was, I don't know, Malcolm. And what's the actor? Peter Capaldi, I think. Right.

[John Oliver]

He swears symphonically.

[Monica Lewinsky]

Right. Which I do too. I try to curb myself, but. Which I love to do. But there's.

[John Oliver]

Yeah. I'm at the point now our kids get an age where you definitely. They definitely shouldn't be swearing. But I think we're about to shift into the point where my advice with cursing is going to be that if you curse, you should do it really well. Yeah. Like, don't do it in a lazy way. Do it in a way that has some music behind it and. Oh, man.

[Monica Lewinsky]

How old are your kids?

[John Oliver]

They are now nine and just turned seven.

[Monica Lewinsky]

Okay. That's. My niece and nephew are seven and nine.

[John Oliver]

Okay. Yeah. So I'm not saying they should be swearing now. I'm just saying they should be thinking about it for the time at which it's.

[Monica Lewinsky]

I've had two funny experiences. So one is I have a plate, like a painted plate that has, in this sort of cursive writing, and it says home sweet fucking home. And my niece was like, home sweet. What's that word?

[John Oliver]

Yes. We have a different relationship to the C word in.

[Monica Lewinsky]

Oh, okay. Yes.

[John Oliver]

I have been sent like key rings or, you know, things with that word on it that as they became able.

[Monica Lewinsky]

That is the word we're talking about cunt. We're gonna say cunt.

[John Oliver]

We're gonna be talking about cunt. There is. And I do, I will never forget, I at least have a key ring with the word. It was from, you know, it was from the woman who runs do you know that place Tea and Sympathy in the West Philly.

[Monica Lewinsky]

Yes, yes, of course.

[John Oliver]

I walked in to get some cris crackers from there one year and she said, I've got something that is absolutely. Makes me think of you every time I see it. And she handed me this key ring with the word cunt written it in wood. So I loved it, put it on my desk at home and it was. I realized that they were getting better at reading when one of them walked up and said, dada, what is this car? Oh, shit. Oh, there's another one.

[Monica Lewinsky]

That'S actually my favorite. The thick of it scene was when it was. Was it Malcolm's birthday and the PM gave him. Prime Minister gave him a cake and it's happy birthday, cunt. And then Malcolm says, well, this could be from a lot of people.

[John Oliver]

Yeah, well that's just objectively very good.

[Monica Lewinsky]

No, no, it was. The other one I had is. I have a. So my best friend from college, we have that with. Oh God, now I'm really going to get it with the word dick. So we got these mugs in LA that said don't be a dick. And I was drinking from my mug when I was FaceTiming with my niece and my sister in law was there and my niece goes, don't be a dick. And we're like, millie, where did you learn that? And she goes, auntie Monka's. It was like, oh, okay, one more thing now to think about.

[John Oliver]

It's not the worst life lesson, right? Don't be a dick. You can try and soften it with less punchy words, but the lesson loses something from just the, you know. Yeah, yeah, don't be a dick. Helpfully monosyllabic. You could, if you were British say, don't be a cunt. Yeah, the rule applies. I just don't know if American ears.

[Monica Lewinsky]

No, no.

[John Oliver]

Ready to hear that.

[Monica Lewinsky]

They don't we. No, no, no. It's like, we'll take away all rights, all women's rights to their body and all their things. Do not. Do not call women cunning. Do not use the C word. That is just too offensive.

[John Oliver]

That's right.

[Monica Lewinsky]

Too dumb to make your own, you know, decisions about your body and all sorts of other. But no. Are your kids, like. Are your kids funny? You know, if you're comfortable talking about some people. Yeah, yeah, yeah.

[John Oliver]

They. I think so. Hope so. God, if they weren't, that would be a problem.

[Monica Lewinsky]

Yeah. Wow. That would be really hard. That would be really hard if you were a comedian and you're like, fuck, my kid is not.

[John Oliver]

Yeah, that's right. Holy shit, this kid. And the worst thing is he thinks he is, and it's brutal to watch.

[Monica Lewinsky]

Yeah.

[John Oliver]

I think also, I guess the reason why it will be such a nightmare is it is in so many ways, the way that I communicate with people. Because you can cut through. You can communicate faster and deeper. I think if you are both laughing at the same thing. I do like, a residency at the Beacon with Seth Meyers.

[Monica Lewinsky]

Yeah.

[John Oliver]

So we see each other once a month. We tend to just laugh a lot when we're talking to each other. Because you're almost going fast. Like, I haven't seen him for a month. You're gonna laugh as much as you can. Make fun of as many things as you can. That feels like a deeper connection to me, similarly with my kids, I think, you know, when you were saying, like, you feel best when you're laughing. I think you want to feel that way with your kids or anyone that you're close to. Right. I think it's the same instinct as saying climbing out of a window when my granddad was dying. I would rather that we laugh together. If this is the last time we're gonna be together, I'd rather that we laughed, because that's.

[Monica Lewinsky]

I mean, I've had moments, I think. I can't think of an example, but I can think of the feeling where I've just gone. Something funny will come in my head and I'll think, oh, but it's too funny. It's too funny now. Like, they'll appreciate the. You know, the humor there. And that's what the phrase. Too soon. Yeah.

[John Oliver]

You know, too soon is subjective. I'm not sure. Too soon to who, exactly.

[Monica Lewinsky]

Yeah, yeah, yeah. No, no, no. It's. And then you're. So now. Is Kate your wife? Do you guys have similar sense of humor?

[John Oliver]

Definitely. And also, like, she was in the Army. Right. So she fought in a way. So they're. They have a dark sense of humor as well. Because, again, how are you going to get through a war? So she tends to, like, each Veterans Day can be a tough day. Right. And I can't understand the things that they went through viscerally. I. Like, I could. I. It helped. I went on a USO tour years ago to at least get the sense of the camaraderie over there. And then I could see why it was so addictive to her, that world. And, yeah, on Veterans Day, they just get together and they just sit in a sequence of bars and laugh.

[Monica Lewinsky]

Yeah.

[John Oliver]

It's not. It is both a somber thing to do. And they'll normally have sore throats from laughing the next day. Right. That feels to me like a good way to deal with something incredibly dark. Have people that you fully understand each other. At which point, if you fully understand each other, why not just laugh and have the most fun you possibly can?

[Monica Lewinsky]

Yeah.

[John Oliver]

Her relationship with comedy is similar in that way, is that she's been drawn to it at moments of darkness. Probably not to the extreme that I am.

[Monica Lewinsky]

Yeah. Yeah. But that's probably a good thing for you.

[John Oliver]

Yeah, I think it's probably safer that way. But, yeah, I totally empathize with the way that her and her veteran friends deal with difficult dates.

[Monica Lewinsky]

Yeah. It's interesting. Do you feel like her sort of coming to understand patriotism through her lens, has that impacted.

[John Oliver]

Oh, that's a great question. I'm trying to think what the really honest answer to that is. Cause I find certain representations of American patriotism borderline psychotic, to be honest.

[Monica Lewinsky]

I get that.

[John Oliver]

And I think there is a danger in thinking of yourself as the good guy all the time, because it doesn't reflect who you are as a country. It doesn't reflect who any country is. That said, when I became an American citizen, it was a meaningful moment to me. I did feel like I wanted to be. Be in American cities because I felt like I belonged here. That's a very dangerous thing to feel if you don't legally, fully belong here.

[Monica Lewinsky]

Right.

[John Oliver]

I remember I used to go back and forth between London and New York a lot early on in the Daily Show. Every time we had a break, I'd go home, see Friends. And I remember landing in New York thinking to myself, literally, as the wheel slows down, oh, it's nice to be home. And then you realize, oh, shit, if that's true, I might need to think about what that means. And it was incredibly tense. That immigration experience is tough even if you have the best version of it. And there's no doubt I had the best version of it. I had Viacom lawyers at that point when I was in the Daily Show. Then I finally got my citizenship in 2019 at the end of 2019. But I realized I thought about it every day. Somewhere at the back of my head was my immigration status. At no point was it not somewhere in my mind. And I have to remind myself now, with all these stories going on, it's so hard. It brings something out of it. Right. It's there, that anxiety that I thought I'd moved past that day that I got my citizenship. I thought it would be gone then. It didn't feel that the relief didn't feel enough.

[Monica Lewinsky]

I've had a sense of understanding a tiny, tiny bit that I empathize with the immigrants who are going through the crisis right now. Right. ICE fuckers.

[John Oliver]

Yep.

[Monica Lewinsky]

Yeah. And just of feeling hunted, like, of feeling unsafe, of like something could happen at any moment now, for me, the hunting was. The consequences of that were nowhere near what they're suffering. I see what you mean, you know, but I've had that of, you know, whether it's being recognized or a paparazzi or there's. There's something. A feeling of unsafety wherever you are. And probably a lot of women feel that in general. I'm not sure I'm making sense right now, but.

[John Oliver]

No, I think you're making total sense. I think that idea of, like, attention being weaponized, that feels like there's a lot of crossover there.

[Monica Lewinsky]

Do you, like, has that being an. An immigrant, being someone who's now gotten their citizenship here, do you feel differently about what's happening or.

[John Oliver]

I don't know if I feel differently about it. I, like, I feel. I. I find that when I talk to immigrants, I was literally talking to the parents of a little kid that I know yesterday, and we very quickly were ended up, like, talking about forms, experiences, what interviews. It's really hard. And so I. I can get sent back to the anxiety that I felt for a long time. Very quick. It is not far from the surface.

[Monica Lewinsky]

Yeah.

[John Oliver]

And it does feel personal. I get. It's one of the things I get really mad about and therefore want to use on our show. Our show to show Americans who may have heard things like come in the right way, just do things the right way, and not fully understand just how antithetical that is to the process that actually exists and that has been either designed or neglected into the state that it's in. It feels worth trying to show people how hard it is.

[Monica Lewinsky]

I also feel, too. I feel so much frustration. Maybe I don't read enough news or listen to enough things, but I feel like we don't hear enough about the Fact that there was a fucking bipartisan immigration bill ready to pass last year. And so that feels like that. That was. I don't even know what the details of it were, so whether I would have been politically aligned with it or not. But to me, anytime I hear bipartisan, I sort of get tingly because it's just so rare. And so you just sort of think about that. We were close to finding something that would have been a step forward. So it's not like.

[John Oliver]

Step forward. Yeah, it wasn't going to end up where you wanted, but, yeah, a step forward is better, always better than where you are.

[Monica Lewinsky]

Right where we are right now, I mean, which I think is pretty unimaginable for many. I mean, at least it was unimaginable to me that we would be rounding people up in our country like this.

[John Oliver]

Yes, I think it was. It felt imaginable to me. Partly because they, like, weirdly, in. In the Trump administration's defense, they've said all of this out loud. Like, they've said it. And I think, I think it's very convenient for people to not believe it because then it feels like you can vote for them and think, yeah, I didn't. Sure, I voted for you, but I didn't vote for.

[Monica Lewinsky]

For that.

[John Oliver]

For people. Yeah, for that. For people being chased across fields. Well, no, you did, though, because they. Okay, I can't believe I'm defending them. But they did say this. They said all of it. You just chose not to believe some of it.

[Monica Lewinsky]

Yeah, yeah.

[John Oliver]

It's rough to watch.

[Monica Lewinsky]

Yeah.

[John Oliver]

Yeah.

[Monica Lewinsky]

Do you. It's interesting. I, you know, with. Come up, for me a little, is thinking about when I moved to the uk, one of the things that I found really surprising and interesting and maybe a little bizarre was just how implicit the culture is. Like, to fit in, you have to observe, Right? Like, that's how I felt. And I feel like the States, it's very explicit. Do this, don't do this. There's a sign that will tell you. And then like in the uk, right, Somebody, when I moved there and someone said, oh, when someone says, you must stay for another drink, it means you've overstayed your welcome. You know? And so, like, that was, you know, or you could get food to go, you could get takeaway, right? But at the time when I was there, so pre Olympics, right, nobody would. You wouldn't see people drinking their takeaway coffee or eating their takeaway food. I would eat my takeaway food on the bus or the tube and I'd be like, oh, nobody else is doing this.

[John Oliver]

Yeah.

[Monica Lewinsky]

Know that. Because if you. If you look around and so that's.

[John Oliver]

A really fair criticism.

[Monica Lewinsky]

I'm not saying it's a criticism per se. It's just, it's. It was like the observation, right? It was the observation. And so I just wonder about with like the difference in politics and. Do you. You know, I don't.

[John Oliver]

I think that might be more to do with just centuries of repression. No one feels like they can tell anyone what to do. It's just that you should already know, which is, you know, passive aggressive in its own way.

[Monica Lewinsky]

Okay. Because.

[John Oliver]

Yeah, you're right. That is a crazy to say to someone, you must stay for another drink using the word must and then be disappointed when they do that feels like that's a you problem, not a their problem. But that's. Yeah, I think there are. There are just like incredible gradations of subtlety with British repression where you're supposed to try and find your way through it as an outsider. I speak British repression fluently, so it all makes sense to me, but as an outsider, I can see that that is completely incoherent.

[Monica Lewinsky]

Yeah, well, it's just it. I mean, it's just. I think if you're someone who has a lot of social anxiety, which I do, that you want to fit in, you know, so you want to make sure you're doing the right thing. And I've, you know, I do.

[John Oliver]

You know what, actually, I found that's interesting. That was your experience as an immigrant. I found coming here almost calming in that way, because I didn't feel like I necessarily fit in in England. So if you go somewhere where you're not supposed to fit in, all of a sudden it doesn't feel like you're right fault anymore. You're not supposed to. So therefore you can just exist in it. No one should. The problem is you went to Britain where the assumption is actually, no, you should. You should go out of your way for this to be a seamless transition in America. I found it much easier because no one expected you to fit in. The moment you open your mouth, you're an outsider. Right.

[Monica Lewinsky]

I think as we wrap up, I wanted to know, how is the sewage plant going?

[John Oliver]

It's still. It's still there. That was the first time I'd seen members of my staff that joined the pandemic.

[Monica Lewinsky]

Oh, really?

[John Oliver]

At all?

[Monica Lewinsky]

Oh, okay.

[John Oliver]

I was in that contagion space and that was.

[Monica Lewinsky]

You bought a. I can't remember what.

[John Oliver]

The show was about. And one of our Writers. Owen had just written a drive by joke about Danbury and then the mayor responded and said that they were going to rename it. That's right. They were going to rename it the Memorial Sewer Plant. Which is very good.

[Monica Lewinsky]

No, no, the John Oliver.

[John Oliver]

That's right. John of Memorial Sewer Plant. And. And I think at that time we were trying to find ways to launder HBO's budget to various charities as well. And so it felt like that that was another opportunity. And I remember being so disappointed in myself by being surprised by how bad that place smelled. Oh, yeah, you really. You don't get to say. This is surprisingly unpleasant to be around when you're standing inside a sewage plant. But yeah, it's still there. It's still there.

[Monica Lewinsky]

And then now Russell Crowe also. Right. He. As a joke. Right, As a joke. Something. Chlamydia ward.

[John Oliver]

John Oliver. That's not a memorial thing. She's John Oliver. Koala Chlamydia Awards.

[Monica Lewinsky]

Koala. I forgot the koala.

[John Oliver]

Monica, Chlamydia is a massive problem with koalas. That's the. No, really, It's a huge issue which is both funny and dark. Yes, they are. Koalas are under existential threat due to chlamydia. Yep. So there is a ward at the Sydney Zoo in my name that is treating koalas for chlamydia.

[Monica Lewinsky]

Russell Crowe.

[John Oliver]

Russell Crowe.

[Monica Lewinsky]

Right.

[John Oliver]

That was again, a moment of incredible connection. We had bought his. He was having a divorce auction.

[Monica Lewinsky]

Okay.

[John Oliver]

And we bought his jockstrap from the movie Cinderella Man. And he responded to that by using the money to start sponsoring this. And I was so impressed.

[Monica Lewinsky]

Yeah.

[John Oliver]

Was Russell Crowe.

[Monica Lewinsky]

Was that before or after the sewage plant?

[John Oliver]

Before.

[Monica Lewinsky]

Okay. So he started the trend.

[John Oliver]

He started the trend.

[Monica Lewinsky]

Okay.

[John Oliver]

He did that.

[Monica Lewinsky]

I'm going to have to figure out how to top them.

[John Oliver]

Yeah, it's pretty difficult.

[Monica Lewinsky]

Like, here's your Alan Oliver mug.

[John Oliver]

It's a really. That koala chlamydia is just. It's the perfect use of money. Especially because it's such a genuine problem. It's such a funny, awful problem. Exactly. And only through this petty sniping across a divorce auction. And it was so great. And. Yeah. Similarly, the mayor of Danbury. I did not think that they were gonna handle that as well as they did.

[Monica Lewinsky]

Yeah. Well done.

[John Oliver]

It's kind of weirdly, life affirming.

[Monica Lewinsky]

Yes. Yeah. So the last question I ask everybody is if there is anything that you are working on reclaiming. And, you know, we use a really elastic definition on the show of, you know, Getting something back that was lost or taken. Oh, no.

[John Oliver]

I was just thinking, asking a British person what they're thinking of reclaiming is a very dangerous road to take. Wait, I mean we lost India. I think there's a whole bunch of places that we. We lost two thirds of the world's landmass. I think if we're playing the long game, we're looking to reclaim that India.

[Monica Lewinsky]

I think that, that you personally. India. You know what's going to happen. They're now going to call it John Oliver's India. Get a call from the.

[John Oliver]

I don't know if I'm trying to. I don't know if reclaiming. I don't think so.

[Monica Lewinsky]

Okay, fair enough.

[John Oliver]

I think anything that I've lost is better gone. I was gonna say dignity, but again you lose.

[Monica Lewinsky]

Yeah. Dignity is. I was just having a conversation with someone about why we don't like why we don't anchor things in our world around dignity more.

[John Oliver]

Really?

[Monica Lewinsky]

Yeah. I just think. I wish we did. You know, it just feels so important to me.

[John Oliver]

Yeah. There's a. I guess one of the things you learn in. I remember there was a stand up in England years ago that said to me something on the way to a gig when I was starting off. He said, once you've bombed 100 times on stage you'll be fine because there is nothing an audience can take from you after that. And I gotta say he was kinda right because I think to lots of people watching a stand up bomb is you get that awful sense of oh my God, this is a nightmare.

[Monica Lewinsky]

Yeah.

[John Oliver]

But there is nothing, there's nothing left. Like your dignity has been so shredded from doing standup that it weirdly kind of slightly inoculates you to the audience loses their power to hurt you. Does that make sense?

[Monica Lewinsky]

Yeah. Yeah. You know what? I had Sarah Silverman on the show and she was talking about how she was a bedwetter like till really late in her. And that the humiliation that came from that inoculated. She was like, oh, stand up. This is.

[John Oliver]

I think that. I think it's kind of true. I think that it gives you this weird false bravado because you just can't. I've lost my dignity on stage so many times that there's either nothing left or there's nothing left to take. Yeah.

[Monica Lewinsky]

Yeah.

[John Oliver]

So I'd say I'd reclaim dignity, but I think I might have lost that above a pub in Mosley years ago on the 99th gig that went horrendously wrong.

[Monica Lewinsky]

Oh, John Ellen Jackson Oliver this has been so great. Thank you so much. Thanks for doing this.

[John Oliver]

Of course. This was an absolute pleasure.

[Monica Lewinsky]

Oh, good. We cleaned. Claiming 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 is Megan Donis for Wondery. Eliza Mills is the development producer. Our managing producer is Taylor sniffin. Nick Ryan is our senior manager, managing producer. Senior producers are Candice manriquez, Wren and Emily Feldbrake. And executive producers are Dave Easton, Erin o' flaherty, and Marshall Louie.