HBO Last Week Tonight host John Oliver recently joined Monica Lewinsky for her Tuesday Reclaiming podcast, and together the two came to an agreement that LWT is the kind of “good trouble” that holds powerful people accountable despite all the evidence to the contrary.

After Lewinsky asked if Oliver was particularly active on social media and Oliver said no, Lewinsky added, “So, I mean, I think something I had to learn was you have to be really mindful if you clapback at people, of just, you know, if you've 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, you know, the punishment’s not worth the crime, and so, when you can bring attention to something, right—”

While Oliver claimed to not be a big social media guy, he admitted to using his TV show in a contrary way, “You're totally right. That’s 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, but 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 to get in trouble.”

The problem with the whole “punch up” idea of comedy is that who is up and who is down is entirely dependent on the view of the comedian. As such, Oliver will never “punch up” at liberals unless it is demanding they be even more left-wing. At the same time, Oliver is a New York elite, and so mocking the average conservative couple, as he did on Sunday, as the kind of people who demand cashiers say “Merry Christmas” in June or get sexually aroused by political violence is punching down.

Lewinsky, however, was amazed at Oliver’s answer, “Yeah. Oh my god, that's an amazing quote, “I do like to get in trouble. Good trouble, right?”

Oliver concurred, “Good trouble, yeah, that’s right, that’s a strong John Lewis drop there… 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 like they are over comfortable. And two, like, you can get away with more sometimes in comedy than you can without it. As you have found, like, in terms of, like, in terms—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.”

Before he became just another hyper-partisan Democratic congressman, John Lewis bravely marched for civil rights in this country and was beaten for it. Let’s not suggest the 1960’s Civil Rights Movement is comparable with hosting a partisan HBO show.

Here is a transcript for the August 11 show:

Reclaiming with Monica Lewinsky

8/12/2025

MONICA LEWINSKY: Are you really active on social media at all?

JOHN OLIVER: No.

LEWINSKY: Okay. So, I mean, I think something I had to learn was you have to be really mindful if you clapback at people—

OLIVER: Yeah.

LEWINSKY: — Of just, you know, if you've 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—

OLIVER: Yeah.

LEWINSKY: — and said something horrible, that it's just kind of the—

OLIVER: Yes.

LEWINSKY: — you know, the punishment’s not worth the crime, and so, when you can bring attention to something, right—

OLIVER: 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.

LEWINSKY: Yeah.

OLIVER: And I probably make, I think you might be a better person than me there, but 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.

LEWINSKY: Right.

OLIVER: I do like to get in trouble.

LEWINSKY: Yeah. Oh my god, that's an amazing quote, “I do like to get in trouble.”

OLIVER: I do. And—in when it comes to work—

LEWINSKY: Good trouble, right?

OLIVER: Good trouble, yeah, that’s right, that’s a strong John Lewis drop there.

LEWINSKY: Yeah.

OLIVER: Yeah, 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 like they are over comfortable. And two, like, you can get away with more sometimes in comedy than you can without it. As you have found, like, in terms of, like, in terms—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.