John Oliver and Monica Lewinsky Bond Over a Shared Hatred of Jay Leno

As most people are already aware, Jay Leno recently took a break from joyriding around Los Angeles in vintage death traps and nursing suspicious injuries to weigh in on the state of modern late-night comedy. 

The former Tonight Show host made headlines for his suggestion that hosts shouldn’t “alienate one particular group” with their polarizing political comedy. “I don’t think anybody wants to hear a lecture,” he theorized.

The statement was blasted for being wildly hypocritical — not just because Leno’s argument against taking political sides was made during an interview with the literal Ronald Reagan Presidential Foundation, but also because Leno himself has a long history of “alienating” political comedy.

One person who clearly wasn’t a fan of Leno’s interview was Last Week Tonight host John Oliver, whose undesirable lectures have earned 30 Emmy Awards (so far). “I’m going to take a hard pass on taking comedic advice from Jay Leno,” Oliver bluntly informed The Hollywood Reporter earlier this month. 

The subject of Leno came up again when Oliver guested on the most recent episode of Reclaiming with Monica Lewinsky. While on the topic of regrettable jokes, Lewinsky brought up Oliver’s previous takedown of Leno. 

During a 2019 segment on public shaming, Oliver interviewed Lewinsky and highlighted the late-night comedy industry’s regrettable history of horrifically cruel jokes made at the 22-year-old civilian’s expense. Oliver didn’t omit himself from this criticism, citing an unfortunate Daily Show episode commemorating “10 suckin’ years” of the Bill Clinton scandal. But he singled out Leno as the worst and least-apologetic host to target Lewinsky, airing a supercut of vicious Tonight Show jokes to back up his claim. 

On her podcast, Lewinsky called Oliver her “champion” for “calling out Jay Leno and making that amazing Dr. Seuss mash-up. I think it was ‘Oh the Places You Can Go Fuck Yourself Jay Leno by Jon Oliver.’”

Oliver was especially peeved at Leno in 2019 because he had, again, criticized contemporary comedians for their impolite political takes. “My particular problem with him at that time as well, was that he had just been, if I’m remembering this right… on TV calling for more civility in comedy.”

Oliver told Lewinsky that he was "irritated" that Leno“ had taken a moral position that week against the other late-night shows,” adding, “none of us are perfect, but I did not like being lectured by him.”

“Neither did I,” Lewinsky agreed. 

Lewinsky also recalled that she was on the list of Leno’s top 10 most frequent Tonight Show targets, but was conspicuously “the only person on there who had not chosen to become a public person.”

“When you sort of called him out for me, it felt meaningful to me, and to my family,” Lewinsky told Oliver. “I, of course, didn’t hear from him,” she noted.

Well, at least he’s apologized to a bunch of anonymous Canadians for someone else’s bad behavior.