Jon Stewart Talks Media, Masturbation, and Making Friends With Pete Davidson

Entertainment icon Jon Stewart joined the Stern Show on Tuesday, sitting down with Howard for the first time since returning to the world of late-night TV. The comedian, filmmaker, and long-time “The Daily Show” host opened up about an array of subjects, from his Apple TV+ series “The Problem with Jon Stewart” to his thoughts on the state of media since leaving his vaunted satirical news show behind in 2015. He also spoke candidly about his friendship with comedian Pete Davidson, how he feels about the successes of former colleagues like John Oliver and Stephen Colbert, and even more intimate topics, like aging and masturbation.

“Getting older is humbling. The other day, I was masturbating, and I had to get my reading glasses,” the 59-year-old guest told Howard. “When you can’t see and you’re like, ‘Why would I masturbate to two people fixing a car?’ And then you’re like, ‘Oh wait, hold on.’”

 “Do you have a certain type of pornography that you watch?” Howard asked.

“I don’t really go for genres. I’m not a plot guy,” Stewart laughed.

“So, you take whatever is on the feed?” co-host Robin Quivers wondered.

“That’s right. Here’s the thing: Why not let the curators at Google do their job. Let me trust the algorithm,” Stewart said, adding, “Howard, you have to keep an open mind as you get older.”

A Paternal Figure for Pete Davidson and Other Young Comedians

Actor, comedian, and Stern Show veteran Pete Davidson’s star has risen to unimaginable heights these past few years, thanks both to his career successes and a string of high-profile relationships with superstars ranging from exes Ariana Grande and Kate Beckinsale to his current partner, Kim Kardashian. Jon, who was recently photographed alongside Pete and Ben Stiller at a Knicks game, said he and the “Saturday Night Live” star turned cultural icon have become fast friends.

“I know Pete real well. He’s just a kid trying to live his life. He’s one of my favorite people,” he told Howard. “I think he’s doing as best he can in that situation when you’re dealing with something that’s so explosive and loaded with all kinds of other things, and I just love that kid.

“How do you know him?” Howard asked

“I think because I’m incredibly hip and with it,” Jon joked. “A lot of times, I walk down the street and people will say, ‘Who’s that Ernest Borgnine motherfucker? I’d like to hang out with that guy.’”

Kidding aside, he and Pete became acquainted on the road while performing stand-up alongside comedians like Dave Chappelle and John Mulaney. “We just became friends from that, and I always have a very paternal instinct [with] those guys because I’ve seen too many of my friends get in trouble and some of them die,” Jon said.

Stewart said it wasn’t unusual for comedians to bond with and even support each other in the workplace. “It’s that back table at the club, and everybody’s doing their sets. It’s the fun of why we got into [comedy] … to not have a real job, to dress like shit, to go out at night and drink and eat lousy food and hang out with other, hopefully, very funny people,” he said, adding, “I do think there’s a stereotype about the comedy world as being sort of not supportive … it is cut-throat to some extent, but there’s a real comradery.”

On John Oliver and Stephen Colbert’s Successes

Speaking of supporting his colleagues, Jon offered nothing but love for “Daily Show” correspondents turned successful late-night hosts Stephen Colbert and John Oliver. “I’ll come downstairs, and my daughter will be watching John Oliver,” he said. “I’m like, ‘Holy shit, Oliver is raising my children. This is awesome!’”

“Did you find yourself getting envious of those guys?” Howard wondered.

“No, no, no,” Jon insisted. “I love what they do, and I love those guys … We had so much fun working together. I don’t have regret or envy or any of those things because I’m astonished at how well shit has worked out for me.”

“I never had that sense that someone else’s success is to the detriment of mine. It leads to such bitterness,” Stewart continued. “I’ve always felt that everybody’s success expands opportunity for you or for anybody.”

“Late Night with Jon Stewart”?

Jon turned late-night TV on its head after taking over “The Daily Show” in 1999, but as he told Howard on Tuesday his career nearly took a very different trajectory. In 1993, David Letterman left NBC’s “Late Night” for CBS’s “Late Show.” His departure left a gaping hole in NBC’s late-night lineup, and Stewart was among a select group of entertainers considered to fill it.

“They got it down to [about five or ten] people, and I was one of those people,” Stewart explained, saying NBC flew the group out to Los Angeles and had them perform a stand-up set at a comedy club. “It was kind of the final round of the auditions and, ultimately, I think it kind of ended there.”

Howard was mystified as to why the network would ask potential late-night hosts to do stand-up comedy, but as Jon pointed out there might not have been too many better options.

“What’s a real audition for a talk show other than [have someone] do it?” he asked. “And everybody sucks at it for the first six months. It’s an art form.”

The “Late Night” gig eventually went to Conan O’Brien. “Conan was not really a performer—he wasn’t a stand-up or anything—but man he created like a very iconic and unique kind of show,” Jon said, adding, “[Late-night] shows are fucking reductive … It’s very hard to do something original.”

Years later, NBC invited Stewart to throw his hat in the ring for “The Tonight Show.”

“Back in that whole Leno era before Conan took over ‘The Tonight Show,’ [then-NBC Universal President] Jeff Zucker had me out to dinner and told me he wanted me to guest host ‘The Tonight Show,’ to be their permanent guest host,” Jon told Howard. “I was like, ‘Does Jay Leno know about this?’ He was like ‘Absolutely. He loves the idea!’ As it turned out, no, he didn’t know, and he didn’t like the idea, and [Zucker was] making the whole thing up.”

Of course, things worked out pretty well for Stewart on Comedy Central where he hosted “The Daily Show” for 16 years, winning over the hearts of millions and amassing countless Emmys in the process. As Howard praised his guest for his achievement, Jon was sure to credit “Daily Show” predecessors, who he said laid a lot of groundwork for what the satirical news show would eventually become.

“They built a nice car, and we were able to modify it to our liking [and] take it in another direction,” Jon concluded.

“The Problem with Jon Stewart” airs Thursdays on Apple TV+.