What Jon Stewart's eclectic pre-Daily Show career tells us about his post-Daily Show future

What will the host do after 16 years as the anchor of The Daily Show? Whatever he wants.

Where next?
(Image credit: Ethan Miller/Getty Images for Comedy Central)

With just two episodes of The Daily Show left before Jon Stewart leaves the anchor chair, the internet is littered with eulogies. At a recent taping of The Daily Show, Stewart took the stage to address all his mourners head-on. "Guys, let me make something clear," he said to the audience. "I'm not dying."

It's easy to feel like we're losing Jon Stewart, and in a sense, we are. The Daily Show is as omnipresent and influential as any politically oriented show on television, and loyal viewers have heard Stewart's unique take on the world, four nights a week, for well over a decade. Whatever the next phase of Stewart's career, he will almost certainly be less visible than he is now.

But it's been 16 years since Stewart took over The Daily Show, which makes it easy to overlook how varied his interests were before then. The odd jobs Stewart took on before finding his niche in comedy have become a part of his legend: bartender, soccer coach, puppeteer, busboy. (The latter inspired the name of Stewart's production company, Busboy Productions.) His run at the New York comedy scene in the late 1980s and early '90s led to work as a writer, host, and comedian — and eventually, to a brief and unconvincing push toward a career as a Hollywood actor.

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Today, watching Stewart's earnest performances in already-forgotten '90s rom-coms like Wishful Thinking and Playing by Heart is like falling into a parallel universe where The Daily Show, as we knew it, never actually happened. If he'd stayed on this track, he would probably have become a B-list Richard Gere instead of an A-list political commentator. More eccentric choices — the sci-fi/horror flick The Faculty, the pitch-black comedy Death to Smoochy — hinted at Stewart's range of talents and interests, but it was clear that Hollywood didn't really know what to do with him.

Stewart's eventual ascension to the anchor chair on The Daily Show, which was vacated by Craig Kilborn in 1998, came after several similar hosting gigs, including MTV's failed The Jon Stewart Show. At the time, neither Stewart nor The Daily Show were the network-defining institutions they've become today, and it took time to hone both the host and the show into the sharp political series it became — and above all, an outlet for liberals frustrated with the Bush administration.

It was a massive, career-making role, and Stewart threw himself into it at the expense of almost everything else he'd attempted up to that point. Since taking over The Daily Show, Stewart has channeled the vast majority of his creative impulses into Daily Show-related projects, including a couple of books and the "Rally to Restore Sanity," an incredibly well-attended live event he co-hosted with Stephen Colbert in 2010. Even his non-Daily Show projects tended to be extensions of his persona; as a two-time host for both the Grammy Awards and the Academy Awards, his jokes tended toward the kinds of things you'd hear on the Comedy Central series.

On the few times Jon Stewart did branch away from his Daily Show persona during his tenure as anchor, the results were at best bizarre and at worst disastrous. It's far from the movie's only flaw, but Stewart's voiceover performance as an evil anthropomorphic spring in 2006's singularly awful Doogal is incredibly distracting. Audiences have long been trained to expect a certain tone from Stewart — witty, patrician, occasionally hectoring — and hearing him deliver lines like "I am the lord of the springs!" never stops feeling incongruous.

With that in mind, it's no surprise that the vast majority of Jon Stewart's most recent credits as an actor — American Dad!, Evan Almighty, The Simpsons, The Adjustment Bureau, The Beaver — are for playing "Jon Stewart." It's what an actor would call typecasting; The Daily Show had become so beloved and all-consuming that he couldn't really do anything else.

But the decision to leave The Daily Show has the welcome side effect of giving Stewart more time and energy to try new things. And given his history, it's easy to imagine countless possible post-retirement projects that would hearken back to the range of skills and interests he demonstrated before he became synonymous with The Daily Show.

He has already committed to lobby in September for an extension of health benefits for 9/11 responders — but after that, his options are basically limitless. Stewart's sole extended hiatus from The Daily Show came when he took a break in 2013 to film the respectfully reviewed Rosewater, the based-on-a-true-story drama about the imprisonment of Iranian-born journalist Maziar Bahari. Does he have any interest in returning to the director's chair for a second feature?

Then there's the staggering number of Daily Show correspondents who have gone on to bigger careers, which proves Stewart has an eye for talent — and given the work he put into building the careers of Stephen Colbert, Larry Wilmore, and Trevor Noah through Busboy Productions, there's plenty of room for him to keep seeking talent out.

There are also side projects; he recently bought a farm with the intention of turning it into an animal sanctuary. And if he ever decided to follow in the footsteps of comedians-turned-politicians like Al Franken and run for office himself — well, it would certainly make for an interesting campaign season.

But the diversity of Stewart's interests before The Daily Show — combined with his decision, after 16 years, to leave it — is a reminder that the most influential political commentator of our time has interests that extend beyond politics. With retirement just a day away, Stewart is already showing more range than he has in years. Last week, he joined Louis C.K. for a surprise set at the Comedy Cellar — the New York-based venue that marked one of the key foundations of Stewart's career in comedy, and where his picture now hangs on the wall.

Fittingly, it's on the subject of standup comedy that Stewart made the most definitive statement about his future plans. When asked at a recent Daily Show taping if he ever planned to return to standup, he responded with an emphatic yes. "That's how I started and that's… I'm sure that's how I will end," he said. "Eighty years old, standing on stage, going 'Ehhhhhh? Come on!'"

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Scott Meslow

Scott Meslow is the entertainment editor for TheWeek.com. He has written about film and television at publications including The Atlantic, POLITICO Magazine, and Vulture.