61 Trivia Tidbits About Jon Stewart on His 61st Birthday

61 That Time He Was on ‘The Nanny’

A throwback to 1997 — two years before he’d helm The Daily Show — when Stewart appeared in The Nanny as Bob “the short Jew.” “That was one of my favorite episodes,” Drescher once told Vogue. “I really love working with really talented comics because I think that they lend themselves to being really fine actors, too.”

60 Always a New Yorker

Jonathan Stuart Leibowitz was born at Doctors Hospital in New York City’s Upper East Side. He grew up in New Jersey and moved to New York to pursue his career. He’s lived there ever since.

59 Growing Up Jewish

Stewart remembers getting punched sometime during seventh grade and being called names like “Leibotits” and “Leiboshits” at school. He once said during an interview, “I didn’t grow up in Warsaw, but it’s not like it wasn’t duly noted by my peers that’s who I was — there were some minor slurs.”

58 He Loathes Deep Dish Pizza

57 Estranged Father

Stewart’s father, Don Leibowitz, left the family when Jon was 11. He struggled to find common ground with his dad, a physicist, and the two eventually became estranged.

56 He Wanted to Be a Professional Soccer Player

A soccer player in high school, Stewart wanted to go pro after college. He joined the College of William & Mary’s team (where he studied psychology). “Jon was very feisty as a player, very high-energy sort of guy,” his coach Al Albert told Moment magazine. Albert would recruit Stewart for the Pan American Maccabi Games in 1993 (basically the Jewish version of the Olympics), and Stewart played on the U.S. team, where he was known as the “locker room joker.”

55 Marred By Injuries

His hopes of playing soccer full-time were crushed, thanks to injuries. His father said that Stewart blew out his knee by the end of his sports career.

54 America’s Most Trusted Newsman

In 2009, a poll done by Time named Stewart, then the host of The Daily Show, “America’s Most Trusted Newscaster.”

53 His First TV Appearance

According to Lisa Rogak, author of Angry Optimist: The Life and Times of Jon Stewart, he was just 9 years old when he made his television debut playing trumpet in a school band on an episode of Captain Noah and His Magical Ark.

52 His First TV Job

Stewart got his first TV writing gig on the 1989 show Caroline’s Comedy Hour.

51 Working for Comedy Central Pre-Comedy Central

Stewart’s biography reveals that Stewart was then hired as a writer on The Sweet Life. The show ran on HBO’s Comedy Channel, which would eventually morph into Comedy Central. 

50 His First Hosting Jobs

The Comedy Channel had “host segments” involving actors or comedians introducing clips of stand-up performances or scenes from classic comedies. Their clip show, Short Attention Span Theater, went from no physical presenter (only dubbing) to Stewart (and others) presenting these culled clips and, later on, even doing a mock news show.

49 Working With Mosquitoes

After graduating, Stewart did some odd jobs before getting into comedy. He worked as a puppeteer for special needs children, briefly as a bartender at places like City Gardens (a punk club where he got to see Joan Jett, GWAR and Butthole Surfers perform), and, at one point, found himself sorting live mosquitoes for the New Jersey Department of Health.

48 Working With The State

In 1992, MTV roped Stewart in to host You Wrote It, You Watch It, a show where viewers sent stories to be acted out on television by the comedy troupe The State. “Jon has that MTV attitude,” Doug Herzog, MTV’s former senior vice president of programming, told The New York Times. “He has a hip, skewed way of looking at things, and even though he can act like a wise guy, he’s also very sweet.”

47 He Almost Replaced David Letterman

When Letterman jumped from NBC to CBS in 1993, Conan O’Brien filled the late-night talk show slot at NBC — but not before the network seriously considered the young Stewart. The Jon Stewart Show was launched on MTV when he didn’t get the job.

46 He Was Offered ‘The Tonight Show’

Stewart told Howard Stern that Jeff Zucker called him and offered being the guest host of The Tonight Show alongside Jay Leno. It turns out, however, that Leno knew nothing about the offer and didn’t approve of it (even though Zucker claimed he did), which was the end of that.

45 He Helped Shape Stephen Colbert

“I didn’t enjoy political humor until I started working with Jon,” Stephen Colbert is quoted as saying in Stewart’s biography. “And then I found I had a stronger (political point of view) than I imagined.”

44 His Film Debut

Stewart is credited as a rollerblader alongside Parker Posey in the 1994 dark comedy Mixed Nuts — his first feature film.

43 He Got Cut From His First Big Movie Role

Stewart initially had a substantial role in First Wives Club, but, as director Hugh Wilson put it to Vogue, the film’s first cut “was longer than Gandhi.” They shaved off 40 minutes, including an entire subplot about Elise Elliot (Goldie Hawn) having herself a rebound fling with a younger character played by Stewart.

42 He Helped Get Tucker Carlson Fired From CNN

It’s hard to believe these days that disgraced right-wing political hack Tucker Carlson once had a show on CNN. But, in the early 2000s, he hosted Crossfire, a nightly current events program featuring yammering debates between liberals and conservatives. In 2004, Stewart went on the show and tore Tucker and co-host Paul Begala a new one. When the show got canceled, CNN president Jonathan Klein cited Stewart’s criticism, saying that he agreed that Carlson’s brand of rantings was hurting America.

41 A Botched Introduction Led to His Name Change

During his second night performing stand-up at a Manhattan club called the Bitter End, Stewart (then still Leibowitz) decided to change his name when the host fumbled his introduction. He also did it for fear of being taunted like he was back in school. 

40 Musings on His ‘Death to Smoochy’ Character

“I think my character may have died at the end. Or not. I don’t know,” he told MTV when asked about a possible sequel. And while he didn’t seem keen on another Death to Smoochy at all, he did share a possible prequel idea: “How did Smoochy get to be in the suit?”

39 On His Acting Skills

“I was never a very good actor. I can do myself like 10 percent madder or 10 percent happier,” he continued. “I give props to the craft of acting ’cause that’s not what I do. Or most comedians. Although there are some that are really good at it.”

38 Inspired By Eugene Debs

Stewart said that, back in high school, he was greatly influenced by American socialist Eugene Debs and was, himself, “a bit of a leftist.”

37 ‘He Created a Genre’

So said Trevor Noah to The Washington Post about the fact that Stewart took the news, satirized it, and turned it into the place young people went to get and process their news before the advent of social media and YouTube. “Everyone thought for a very long time that comedy was an escape from seriousness,” Noah explained. “‘No, we just make the jokes. Don’t say anything real.’ And I think what Jon Stewart successfully did was he inverted that idea and he said, ‘No, comedy, and especially satire, will be the home of authenticity and difficult subjects and ideas.’”

36 An MTV Hit

The Jon Stewart Show was one of MTV’s most popular TV shows, second only to Beavis and Butt-Head in ratings.

35 His Modus Operandi

When asked during an AMA on Reddit how he and the writing staff of The Problem with Jon Stewart came up with topics for each episode, he shared: “It generally begins like Festivus with an airing of the grievances. We try to separate personal pet peeves from systemic fuckery. And then, and I cannot stress this enough, you’re going to need index cards.”

34 On Why He Quit ‘The Daily Show’

“It’s not like I thought the show wasn’t working anymore or that I didn’t know how to do it,” Stewart said after 16 years of running The Daily Show. “It was more, ‘Yup, it’s working. But I’m not getting the same satisfaction.’ These things are cyclical. You have moments of dissatisfaction, and then you come out of it, and it’s okay. But the cycles become longer and maybe more entrenched, and that’s when you realize, ‘Okay, I’m on the back side of it now.’”

33 Post ‘Daily Show’

Never forget that Stewart’s first public appearance following his departure from The Daily Show and subsequent retirement from the limelight (if only ever so briefly) was to get body slammed by John Cena at WWE’s SummerSlam simply because his kid’s a huge wrestling fan.

32 A Favorite News Source

By the time Stewart was done with The Daily Show, Pew Research reported that 12 percent of online United States citizens claimed they got their news from his talk show. It was the same number of folks who relied on USA Today as their go-to news source.

31 The Susceptible Boy

That was, as reported by The New Yorker, what staff members called him during The Jon Stewart Show because he was extremely anxious and also extremely prone to catch whatever cold was going around.

30 His Brief BBC Show

Before Stewart hit it big with The Daily Show, he briefly hosted a talk show called Where’s Elvis This Week? that only saw six episodes and aired in the U.K. on BBC Two. 

29 His One ‘Daily Show’ Disappointment

When asked about his biggest regret during his Daily Show tenure, Stewart mentioned his 2011 interview with Donald Rumsfeld, saying he should’ve gone harder on the former secretary of defense. “He just went into the general gobbledegook — ‘Mnah mnah mnah, well, you have to remember, it was 9/11 mnah mnah’ — I should have pushed, but he’s very adept at deflecting,” Stewart told The Guardian. “That interview with Rumsfeld went shitty, but it’s still just an interview. He’s the one who has to live with the repercussions of what he really did, so there’s nothing that could happen on my show that carries that same level of regret.”

28 Crediting Letterman

Stewart told Vulture that he never really felt like he had arrived until his first appearance on Late Night with David Letterman. It was, in any case, a nerve-racking experience. “When I walked onstage, I blanked,” Stewart remembers. “The audience is dark, and there’s just a little red light. At that moment, you’d realize it’ll be really quiet here if I don’t talk.”

27 On Fact-Checking in Comedy

“We’re just going off our own instinct of, ‘What are the connections to this that make sense?’” Stewart explained to NPR while discussing creating a Daily Show episode. “And this really is true: We don’t fact check (and) look at context because of any journalistic criteria that has to be met; we do that because jokes don’t work when they’re lies. We fact-check so when we tell a joke, it hits you at sort of a gut level — not because we have journalistic integrity. Hopefully, we have a comedic integrity that we don’t want to violate.”

26 He Hosted ‘Elmopalooza!’

In 1998, Sesame Street did a special called Elmopalooza! to celebrate its 30th anniversary.

25 Roommates with Anthony Weiner

Back in the day, Stewart shared an apartment in NYC with the now-former Brooklyn congressman who fell from grace after a string of sexting scandals led to him having to register as a sex offender.

24 Blind Date

Stewart met his wife, Tracey McShane, on a blind date and, according to his biographer, proposed to her via a New York Times crossword puzzle. The two got hitched in 2000 and have been together ever since.

23 Preoccupied With Poop

Stewart and McShane, a veterinary technician, run an animal sanctuary near their home in New Jersey. This means, for most of his days, having to deal with his town’s rules about how much animal poop is allowed to accumulate on a particular size of land. “So you find yourself in a situation where you’re like, ‘Oh, the animal got out on the thing, but, you know, we’re pooped out. We’re at our poop capacity,’” he told The Washington Post.

22 The Voice of the ‘Disenfranchised Center’

In the 2002 interview with The New Yorker, Stewart explained the voice of The Daily Show (at the time) as such: “It comes from feeling displaced from society because you’re in the center. We’re the group of fairness, common sense and moderation.” On refraining from taking sides when it came to polarizing issues, he simply said: “The disenfranchised center doesn’t give a shit.”

21 On Not Casting Iranian Actors in His Iranian Drama Film

Stewart made his directorial debut in 2014 with the political drama Rosewater, based on the memoir Then They Came for Me by Iranian-Canadian journalist Maziar Bahari, which recounts his brief imprisonment in Iran in 2009. Bahari is portrayed by the Mexican actor Gael García Bernal; when folks questioned why Stewart didn’t cast an Iranian actor, he told The Guardian, “If I was Iranian, I’d probably look at (Bernal) and be like, ‘Really? Those Rs? Come on, man.’ But Maziar was our touchstone, and if he wasn’t bothered by it, I wasn’t bothered by it. My original vision was, ‘Maziar, we’re going to do this in Persian and use real prisoners, and it’s going to be only Iranians!’ And he was like, ‘Don’t you want people to see it?’”

20 He Was Originally Offered Jimmy Kimmel’s Spot

In 2002, ABC reportedly offered Stewart a talk show that would run after Nightline. That show eventually became Jimmy Kimmel Live!

19 He Has Two Grammys

Stewart has won numerous awards over the years, including five Peabody Awards and 23 Emmys. He even has two Grammys — one he got in 2005 for America (The Book): A Citizen’s Guide to Democracy Inaction in the Best Comedy Album category, and one in 2011 for his spoken word album, Earth (The Book): A Visitor’s Guide to the Human Race.

18 Not a Frat Boy

Stewart was a member of Pi Kappa Alpha for a full six months before dropping out because it just wasn’t his vibe. “As fun as it was to have parties in that house, it wasn’t worth the pressure of living up to someone else’s expectations as to what you’re supposed to be and going to meetings where they had parliamentary procedure to discuss a toga party,” he once quipped.

17 The Mark Twain Prize

In 2022, Stewart became the 23rd recipient of the Mark Twain Prize for American Humor.

16 On His Apple+ Show

In October, Apple+ announced the cancellation of Stewart’s show, The Problem with Jon Stewart, with insiders claiming creative differences concerning coverage of China. This prompted lawmakers to demand Apple Inc. explain precisely why they were pulling the plug on the show, for fear that it might be perceived as Chinese censorship.

15 On Working Tirelessly to Advocate for the Rights of First Responders

14 A Fan of Stoicism

When once asked why he’s such a staunch advocate for and so charitable toward military and first responders, Stewart said he revered their stoicism. “Members of the military and their families don’t often reach out for help when they need it,” he explained. “And I think too often we depend on them, and yet when the time comes for them to depend on us, we’re not there for them. So I try to help push along the idea that the least we can do for them is repay their service and selflessness with support.”

13 Spring Break Host

Back in his MTV days, Stewart hosted MTV Spring Break ’93 Blind Date from Daytona Beach alongside Melissa Rivers. You can watch him and his hip reverse cap at the 52:36 mark below.

12 Stewart Tried to Create ‘The Colbert Report’ Earlier

Stewart founded his production company, Busboy Productions, in 1998. In 2002, he approached NBC and told them he wanted to create a show for Colbert. They declined, with Stewart eventually getting a deal with Comedy Central and The Colbert Report debuting in 2005. It was Busboy Productions’ first show.

11 He Almost Quit ‘The Daily Show’

Taking over from Craig Kilborn at The Daily Show was no simple task, and Stewart once told Colbert that it was challenging adjusting to working with Kilborn’s team. “What I did not realize is, a lot of the people who worked there were assholes,” Stewart said. “I walk in the door, into a room with the writers and producers, and the first thing they say is, ‘This isn’t some MTV bullshit.’ And then I was told not to change the jokes or improvise.” Stewart went on, saying he immediately called his agent and told him to find a way to get out of the deal. “I had to be talked down from a moderately high cliff,” he said.

10 Two Years

That’s how long it took Stewart to shape The Daily Show to his liking and standard. “He didn’t rock the boat. Instead, he used that first year to gradually make the adjustments necessary to create the foundation for what the show would eventually become,” Daily Show writer J.R. Havlan told The Hollywood Reporter. “I’ve always marveled at his patience, focus and foresight during that time, and I can assure you that I’m extremely grateful for it.”

9 His Miramax Deal

In 1995, Stewart landed a three-year movie deal with Miramax and starred as the romantic lead in Playing by Heart and Wishful Thinking. He also had a supporting role in the rom-com Since You’ve Been Gone.

8 When He Changed the Title of ‘The Daily Show’

During the 2007-2008 Writers Guild of America strike, Stewart changed the show’s name to A Daily Show to symbolize that the show was incomplete without its writing team. 

7 His Least Favorite Guest

Stewart stated that Hugh Grant was his least favorite celebrity guest on The Daily Show. Grant was reportedly terrible with the crew backstage and complained about the clip the show chose to promote his movie, Did You Hear About the Morgans? Stewart subsequently banned Grant from the show afterward.

6 A Favorite Interview

“You know, what I appreciate about him is he clearly believes what he is saying,” Stewart said about interviewing Ralph Nader. “He really believes it. It was nice to see somebody with passion.”

5 His Cameo in ‘Gravity Falls’

Stewart voiced a cartoon kitty in Gravity Falls. Of course, it’s not just any cartoon cat. It’s a hot pink cartoon kitty called Judge Kitty Kitty Meow Meow Face-Shwartstein. “Jon and I talked in the Daily Show coffee room for 15 minutes, and he told me he loved watching Gravity Falls with his kids and even does a Grunkle impression around the house,” creator Alex Hirsch said. “I’ve been obsessed with The Daily Show since high school so to call it a dream come true was an understatement. I’ve been looking for an excuse to get him on the show ever since.”

4 The Lost Animated Show

In 2015, Stewart teamed up with HBO to make “an animated parody of a cable news network with an Onion-like portal.” In 2017, the project was canceled, with the statement explaining that “there were technical issues in terms of production and distribution that proved too difficult given the quick turnaround and topical nature of the material.”

3 He Wants to Direct More

Stewart last directed the 2020 political satire Irresistible, starring Steve Carell, and has expressed his desire to direct more movies in the future.

2 He’s Not Running for President, Okay?

Since his rise as one of the most legendary talk show hosts in television history, many liberals have called for Stewart to run for president because, well, folks get desperate sometimes. Most recently, when speculations of Tucker Carlson running for president in the 2024 election started swirling, there were fresh calls for Stewart to run as the opposing Democratic candidate. However, Stewart made it clear that he’s not even entertaining the idea.

1 He’s a Bruce Springsteen Nut

Stewart has been vocal about his love for The Boss in many, many interviews, so it makes sense that he’s given speeches at not one but two ceremonies honoring the New Jersey native.