(Andre Chung for The Washington Post)

Jon Stewart cares less about his legacy than you do

On the eve of entering the comedy hall of fame, the former host of ‘The Daily Show’ is already in his second act

17 min

Jon Stewart could talk about poop all day. Actual animal feces. Manure load. The comedian who was the country’s moral compass during the Bush and Obama years, the guy with the fake news show on Comedy Central who in a 2009 Time poll was named America’s most trusted newscaster — and who is now, as he loves to point out, very, very old (at 59) and completely ravaged by age — spends a lot of his spare time thinking about pigs and cows and horses and where they take a dump.

“Generally, they are not particularly careful about where they make their bowels,” he explains.

Seven years after he retired from hosting “The Daily Show,” just as Donald Trump was starting what seemed in 2015 to be a kind of a joke of a campaign, Stewart is calling by video chat from Hockhockson, N.J., where he lives near a 45-acre animal sanctuary he runs with his wife, Tracey, a veterinary technician. The town regulates how much animal waste is allowed to accumulate on certain pastureland. “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,’ ” says Stewart.

Stewart has called himself a “turd miner” in his comedy work, too. For 16 years as the host of and creative force behind “The Daily Show,” he was panning for truth and laughs through the sludge of politics and cable news — while also co-creating “The Colbert Report” and racking up 22 Emmys, five Peabody Awards, two Grammys and two New York Times best-selling books along the way. When he started in 1999, no one expected him to turn a satirical riff on the news into appointment national television, and on Comedy Central, no less.

But he was funny and gave catharsis to a country (well, mostly liberals) grappling with 9/11, the Iraq War, the financial crisis and the rise of 24-hour punditry — in an age before social media, or even YouTube. As distrust in government and media grew, Stewart was where young people turned to make sense of the world.

“He created a genre,” says Trevor Noah, Stewart’s successor at “The Daily Show.” “Everyone thought for a very long time that comedy was an escape from seriousness. ‘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.’ ”

The show worked because “he built it in his image … it was so uniquely about him,” says Lorne Michaels, creator and executive producer of “Saturday Night Live.” He picked the satirical targets, he brought in correspondents who made him laugh, he interviewed serious people without being a bully, Michaels explains. It’s what Michaels and David Letterman did to build successful shows: “You build it around the things you’re really interested in.”

On Sunday, Stewart will become the 23rd recipient of the Mark Twain Prize for American Humor from the Kennedy Center. It’s essentially an induction into the comedy icons’ hall of fame, alongside Michaels, Tina Fey, Eddie Murphy, Bill Murray. Stewart gave speeches at the Twain Prize ceremonies for both his buddy Dave Chappelle and his hero George Carlin, so he knew what it meant when the Kennedy Center called. But still, it was weird. All this? For turd mining?

“I remember thinking like, Oh, that can’t be. I’m a young comedian,” says Stewart. “And it took me a little bit to go like, Oh right, I’m old. I get it now. I’m that guy. I’m the guy they want to be like, ‘We’re gonna throw you a party because we don’t know how long this is gonna go.’ ”

Thing is, Stewart is young, at least relative to other big-time comedians who’ve left their history-making shows. And he’s not done. In fact, he just started experimenting with a second act in streaming TV that’s a lot like the show that made him famous. It’s an open invitation for comparisons and criticisms — a red cape in the Internet bull ring — that seems to demonstrate a total lack of concern for preserving his legacy.

Which makes this an odd time to receive a legacy award.

Stewart, a lot like your dad on Zoom, has positioned his camera so that I am either closely examining his pores or frequently talking to the top of his head. He’s in his home office and has on glasses and a gray sweatshirt. But talk to anyone who worked with him on “The Daily Show,” and they’ll say he wears the same outfit every single day: a T-shirt, khakis and a Mets cap, like Steve Jobs and his turtlenecks. “It’s possible that he had 20 different versions of the same T-shirt and pants combo,” says Samantha Bee, who was “The Daily Show’s” longest-running correspondent. As a joke, the staff bought him that exact outfit for his 50th birthday.

Tracey did the decorating, he says, “because she knows that left to my own devices, my office would be milk crates.” Behind him are photos of his kids, Nate and Maggie, black-and-white photographs of the Jersey Shore taken by his good buddy Bruce Springsteen, and, most prominently displayed, a large blowup of the 1972 New York Knicks championship squad with Clyde Frazier and Bill Bradley.

“That’s up there to remind me that they did win once, like 50 years ago,” he says.

That Jon Stewart still lives in New Jersey is very Jon Stewart. At one point in his younger life, he says, “the only band that I had seen more than Bruce was a band called Backstreets, which was a Bruce tribute band.”

He comes from a long line of Jewish immigrants. One grandmother lived through the pogroms in Russia. One grandfather, from a Jewish community in Inner Mongolia, fled Japanese invasion. Stewart and his older brother Larry were raised in Lawrenceville, N.J., near Princeton. Their father, Donald, a physicist, left their mother, Marian, a teacher, when Stewart was 11. Eventually, Stewart and his father became estranged.

It was on his second night doing stand-up in his 20s that he became Jon Stewart. He’d been born Jonathan Stuart Leibowitz, as Trump once helpfully reminded the world on Twitter. But the emcee had trouble pronouncing it and, as Stewart said in his Twitter war with Trump, “Can’t an overrated Jew have a complicated relationship with his dad without being accused of hiding his heritage?” (They reconciled by the end of his father’s life.)

Repeated failure is the backbone of any showbiz beginning, and Stewart had a pretty spectacular run.

“I always felt estranged from the world,” Stewart says. “I always felt like, this is a brain that would like to be in the world but not participate in it. It doesn’t work right. There’s something wrong that is not valuable to what appears to be normal society.”

He’d dreamed of being a professional soccer player but knew it was a long shot and, anyway, blew his knee out in college at William & Mary.

So he moved back to Jersey and tried real jobs, only to get fired again and again. Porter in a bakery. Autoclave guy at a cancer-research lab. Sorting live mosquitoes for the New Jersey Department of Health. His own brother fired him from his first job as a stock boy at Woolworth’s. Later, in New York, he drove a catering van and managed to get it towed with the food he was supposed to drop off at a holiday party still inside. “I had to chase that f---ing van all the way from Midtown to the impound lot,” he says.

That comedy might be the answer, he says, “I’d always had that in my head.” But it wasn’t until he started bartending at City Gardens, a legendary punk club where he’d watch Joan Jett, GWAR and Butthole Surfers that he could see a possibility of a different life. Maybe on a stage. Not behind a bar. Not in Trenton. Drinking himself into oblivion at the other bar where he worked, which was located under a liquor store, he had an epiphany. “I was like, ‘Okay, this isn’t how I’m going to die.’ ” He got a six-week lease in New York, “and just said, like, ‘I’m going to go where I think my brain will feel at home.’ ”

Things you learn about Jon Stewart from talking to him and his friends

“Jon was a broken-down soccer player who thought he was funny, and he was funny,” says Denis Leary, who came up in the clubs with Stewart, alongside Colin Quinn, Chris Rock and teenage Dave Chappelle working for beer money at Catch a Rising Star or a plate of hummus at the Comedy Cellar. His gift, says Leary, was being so charming you didn’t realize he was also this angry, ranting guy. “He can be really goofy, and at the same time, before you knew it, you’d be like, ‘Oh wow, that’s a complete obliteration of the Reagan AIDS policy he just did.’ ”

It took six years, but in 1992, Stewart did the first of many stand-up sets on “Letterman” — his ultimate goal — with jokes about famine in Russia, immigrants, bigotry, nuclear war, Israel, and imagining Jesus, Moses and Muhammad as rivals on the same high school swim team. Then he went home and the high ended. “I was like, I still live in a hovel,” Stewart says. “It was an illegal sublet with a hole in the floor where you could see rats running around.”

Hosting gigs came and went, until in 1993, MTV gave him “The Jon Stewart Show,” its version of a late-night talk show. Stewart wore a leather jacket; interviewed MTV VJs; did goofy sketches, like a version of Orpheus in which a puppet Tori Spelling is rescued from Hades; and showcased musical guests like Faith No More, Ol’ Dirty Bastard, and “Weird Al” Yankovic, who were too hip for the networks. If he was bored or had greater ambitions, he didn’t show it.

“The secret of Jon is to not be living in the future, but to be living in the present and enjoying the now and not going, ‘Why do I have to interview this dumb person?’ ” says Steve Higgins, a writer on “The Jon Stewart Show” and now a longtime writer-producer on “Saturday Night Live.”

When Stewart took over “The Daily Show” in 1999, from its inaugural host, Craig Kilborn, he was that guy from MTV who’d had his eponymous talk show canceled after Marilyn Manson burned a Bible onstage.

It was going to get canceled anyway, but that’s the better story.

Expectations were low, and freeing. “We were these hacking pirates launching ourselves into legitimate news circles and making fun of everything around us,” says Colbert, describing the experience of running around the 2000 presidential conventions as a correspondent, ambushing delegates and pushing out four or five shows. Steve Carell, meanwhile, managed to talk his way onto John McCain’s bus.

Stewart talks often about being raised on the tenets of “The Emperor Has No Clothes.” And that philosophy permeated the show. He laid it out in his “Bull---t is everywhere” rant on his final show: “If you smell something, say something.”

That’s why Stewart went on CNN’s “Crossfire” in 2004 and famously eviscerated co-host Tucker Carlson, telling him that the show was “not just bad, but hurting America,” and that he was doing theater, or performing “partisan hackery” in a bow tie, instead of actually fostering debate. And when the show got canceled three months later, CNN’s president said Stewart’s appearance was a factor.

Cut to 18 years later and Carlson is the biggest star on Fox News, with 3.4 million viewers a night. His pro-Russian stances are being distributed as Russian propaganda. He’s called the Ukraine crisis a mere “border dispute” and asked what’s so bad about Vladimir Putin (“Has Putin ever called me a racist?”).

Does Stewart think that, by knocking him down, he may have inadvertently given Carlson the incentive to rise and be more Tucker Carlson-y?

“There’s mythologizing as far as, like, a villain origin story,” Stewart says. “Not even close. Like that dude has been that dude forever and just found his place. It’s not that the crystal found the right home and suddenly the Fortress of Solitude was built. I don’t think he’s any different than he’s ever been.”

Other late-night hosts have been missed when they left, but none with the urgency of Stewart during the Trump years. He was greeted with raucous cheers and standing ovations whenever he came on Colbert. There was lamentation, sometimes anger among liberals who thought he’d abandoned them in their time of need.

In his stead, though, was a political comedy landscape dominated by people whose careers he’d either started or nurtured: Colbert, Samantha Bee, John Oliver, Trevor Noah, Michael Che on “Weekend Update.”

For the most part, since he left the show, Stewart has led a groundhog-like existence, puttering away in happy seclusion with Tracey and their now-teenage kids and popping his head out every once in a while to do stand-up gigs with Dave Chappelle or rant about Trump’s “gleeful cruelty” on “The Late Show with Stephen Colbert.” His running gag was to physically pop out from under Colbert’s desk — his hair white, having grown that classic beard of a former late-night host gone feral — claiming he’s been living there this whole time.

He has also frequently popped up in Washington to shame Congress into “showing a baseline of humanity,” as he put it in a recent Reddit AMA. In 2019, he called out Congress’s “rank hypocrisy” and “shameful” lack of action in impassioned testimony for the reauthorization of the September 11th Victim Compensation Fund. He’s spending the week before his Twain Prize celebration going to rallies in Wilmington, N.C., and Kansas City, Mo., supporting legislation to provide additional funding for veterans dying from exposure to toxic burn pits.

Stewart says he left “The Daily Show” so he wouldn’t miss his kids growing up. And for years he’s stuck to that. His first public appearance after retirement was going on WWE SummerSlam to get body slammed by John Cena, because his son is a wrestling fanatic.

He’s gone vegetarian, is learning Brazilian jujitsu with his son and has taken up drumming. “The fact that he drums for an hour or hours a day and didn’t mention it to you is a little bit odd,” says good friend Jimmy Kimmel.

Stewart easily could have kept up that pastoral pace. He could be getting coffee with comedians in cars like Jerry Seinfeld or starting a travel show like Conan O’Brien.

Instead, he’s Shaun White doing the halfpipe at 35, or Michael Jordan returning to the Bulls after the baseball years.

In January 2021, he started his first Twitter account with the energy of, well, a comedian who hadn’t spent four days a week for the past half-decade thinking about and reacting to Trump.

Tweet No. 3: “So…if I do really well on here I get to be President, yes?”

Then in September, he jumped right back into the turd mines, debuting his new Apple TV Plus show and podcast, “The Problem with Jon Stewart,” which might as well be the fraternal twin of “The Daily Show.” It’s a direct outgrowth of a 2010 episode of “The Daily Show,” when Stewart convened a panel of 9/11 first responders as a way of shaming Congress for stalling on the victims compensation bill. It passed before the end of the year, and firefighters on that panel have largely credited Stewart.

Sure, there are differences. The streaming show isn’t on every night. It’s just eight hour-long episodes, with accompanying podcasts, each devoted to a single issue, like critical race theory and gun control. Every show has a panel discussion with real people and an interview with a power broker (former Disney CEO Bob Iger, SEC Chair Gary Gensler).

But he is back behind a desk, delivering the kind of complex monologues on serious issues that he calls “geometric proofs for fart jokes.”

He’s also resumed his role as a political lightning rod, particularly when semi-conservative provocateur Andrew Sullivan wrote a lengthy Substack saying Stewart “ambushed” him into making him look racist. A quick Google News search will bring up recent articles from Fox News or the National Review about his “sad demise” or how his “super-woke” new show is a flop. On the left, he’s been accused of sympathizing with oil companies and defending Joe Rogan, after Stewart said he’d rather debate him than cancel him.

Even the name of his show, he says, is intentional bait for conservative pundits to see how many write screeds about what his real problem is. (Sullivan took the bait.) “The fun is in watching the laziness, the people who are coming up with their hot takes … and they’re just laying down trope after trope,” Stewart says.

Glory and humiliation are both possible outcomes, a lot like doing stand-up. What he did on “The Daily Show” is complete and untouchable — a 16-year mic drop. How do you follow up being the voice of a generation when the next generation either thinks you’re lame or has no idea who you are? How do you jump back into a game you defined that has evolved without you? And why try?

Perhaps it has to do with how animated Stewart gets telling me about the time he bombed — hard — at Radio City Music Hall in 1999. So hard “I didn’t even know 6,000 people could be that quiet,” he says. So hard that Shirley Jones hugged him. “I don’t even know the woman,” he says.

You take risks. That’s comedy. “Isn’t that what’s seductive about it?”

The bombing?

“No! It’s the uncertainty of it,” he says. The volatility. The thrill of riding that line.

“You know, if somebody said to me, ‘Are you nervous about going out there again with something new?’ It’s like, ‘I mean I guess, but what’s my option? Yeah, I’m nervous about it. So I’m not gonna say anything to anybody ever again?’ ”

Stewart’s trying something new. He’s still got stuff to say.

“This is the life we’ve chosen,” he says. “This is what we do.”