Retirepocalypse 2015: What You Can Learn From Jon Stewart’s Career Non-Indecision

Noooooooooo! Okay, people, let’s get through this together.

Retirepocalypse 2015: What You Can Learn From Jon Stewart’s Career Non-Indecision
[Photo: Kevin Fitzsimons, courtesy of Comedy Central]

Note: this story originally ran the day after Jon Stewart said he would be leaving The Daily Show. The post still offers fresh insights and works well as a tribute to Stewart’s incredible run and sui generis approach to comedy, so we are re-surfacing the piece today to celebrate (and, let’s face it, mourn) his last day at the DS.



Last night, just before throwing to a clip of a chimp washing a cat, Jon Stewart announced that he will be retiring from The Daily Show after 17 years at the faux-anchor desk. It may not have been as dramatic as Howard Beale announcing his imminent suicide on air in Network, but Stewart’s decision sent a ripple across the media, social and otherwise, and is likely to be discussed for months to come.

A journeyman stand-up and character actor when he joined The Daily Show, it’s interesting that Stewart framed his announcement as a referendum on work: “Seventeen years is the longest I have ever in my life held a job by 16 years and five months,” he said. “The upshot being, I am a terrible employee.”

Stewart called working on The Daily Show “the honor of my professional life,” and expressed his gratitude to the executives who hired him 1998 and the team he worked with, as well as his audience. The host’s graciousness didn’t feel tactical (praise up; praise down; thank the customers), but rather an expression of a genuine humility he’s managed to hold onto even as his show has won 20 Emmy Awards, played host to sitting presidents, former heads of state, and Jennifer Lawrence.

Not for nothing is Stewart’s production company called Busboy and its “vanity card” features the sound of Stewart whispering his apologies for spilling a drink. This is a guy who remembered where he came from and understood that work—busing tables, telling jokes in godforsaken Ha-Ha Holes in Bumfuck, or hosting the Oscars—is its own reward.

What else can you learn from Jon Stewart’s career? For this, we turn to Fast Company‘s bullet points.


It’s OK To Be A Late Bloomer

Before Stewart took over as host of The Daily Show with Jon Stewart in 1998 (the show’s name suddenly making a whole lot more sense), he’d bounced around comedy and acting for a decade. Perhaps you remember his short-lived MTV show or his turn as “Bob the Jewish Doctor” on The Nanny. Stewart’s name had been bandied about for several high-profile gigs, including replacing David Letterman (before someone named Conan O’Brien was given the job), but nothing seemed to last very long until he was tapped to replace Craig Kilborn, The Daily Show‘s original host who’d famously flamed out in 1997 after making sexist comments about the show’s co-creator and producer, Lizz Winstead. Suddenly, at 35, Stewart had a steady gig and history—or at least a lot of good comedy—was made.

The takeaway: It doesn’t matter if your resume has more weird descriptions than a Greek diner menu: When you find the right job, it’ll be right, even if you’re practically middle aged.

Be Humble

In a 2002 New Yorker profile, writer Tad Friend described Stewart this way: “Though he quit his fraternity at William & Mary after six months because he hated the enforced friendships and the hazing, he still exudes a fraternal ‘Need a hand with that keg?’ air. He calls his colleagues ‘chief’ and he shakes the cameramen’s hand after each show.”

Stewart seemed to understand that every job is just a gig and that the way you treat the people around you is as important as what you do. Sure, he had some early missteps (there’s a story about Stewart throwing a newspaper or a script at show co-creator Madeleine Smithberg’s head,) but by all accounts, Stewart was a respectful and decent to his people and worked hard. In the same piece, Stewart told Friend, “When I tended bar, after college, I was always happier behind the bar, not out rocking to the band.”

The takeaway: Do the work. Be good to people.

President Barack Obama, Jon StewartPhoto: PictureGroup

Surround Yourself with Talent

Yes, his name was in the show’s title—which was probably so weird when Craig Kilborn hosted—but Jon Stewart was merely the first among equals. He helped boost the careers of Stephen Colbert, Steve Carell, John Oliver, Rob Corddry, Samantha Bee, Wyatt Cenac, Olivia Munn, Henry Kissinger, and countless others. Whenever he won an Emmy (which was often), Stewart brought up his writers—a rumple of bespectacled nebbishes who’d just barely managed to adjust their comb-overs before galumphing on stage—and shared the spotlight with them. He did this for many reasons having to do with pity, but also because he understands that without a team, he’d probably be galumphing alone into his agent’s office asking if Fran Drescher called about a Nanny reunion special.


The takeaway: Writers are losers. Also, talent respects talent.

Keep It Interesting

In his departure announcement, Stewart said he had “a lot of ideas… I got a lot of things in my head.” In November he’d turned 52 years old (that’s 364 in comedian years) and he’d just released his directorial debut, Rosewater. Perhaps the anchor chair had gotten a bit too comfortable for him and he’s ready for the next challenge. There is an election coming up in 2016 and he was already drafted to run once. Whatever he decides to do, he’ll be doing it on his own terms, something we all can learn to do more. No job, no matter how great or how many times it lets you interview Jennifer Lawrence, should keep you complacent. Jon Stewart has ideas! How exciting is that? The smart money says we’ll hear from that kid, and I don’t mean a postcard.

The takeaway: Thanks, Jon.

Jon Stewart’s Best Moments: