A Timeline Of Jon Stewart’s ‘Daily Show’ Years, From Nearly Quitting Until Announcing His Retirement

As you’re all aware by now, Jon Stewart will be leaving The Daily Show sometime later this year (July, September, or December, depending on how it works out with Comedy Central). Twitter is rightfully weeping over the loss of, frankly, the best newsman of this generation (though, we are already considering worthy replacements).

For a guy who has been in the public life for as long as Jon Stewart, it’s remarkable, really, that he’s never been a part of a huge scandal, his personal life has managed to remain personal, and for 16 years, he’s not only been a steady, guiding force of not only The Daily Show, but he’s been the biggest cheerleader for the people that have come out of it (The Daily Show spins out nearly as much talent as Saturday Night Live these days).

Granted, it’s not always been easy for Stewart. There have been a few lows to go along with the many highs along the way. Let’s take a quick look back at the highlights during his tenure on The Daily Show.

January 1999 — After toiling away for years with a couple of failed talks shows, getting passed over for Late Night by Conan O’Brien and The Late Late Show by Craig Kilborn, Stewart finally settled in for the longest job of his career, as host of The Daily Show. It was a rocky start for Stewart, however. In fact, he nearly quit The Daily Show over his contentious relationship with the Kilborn holdovers

“What I did not realize is, a lot of the people who worked there were assholes,” Stewart said. He ultimately decided to stick around for the job although he said that it took him about two and a half years to get comfortable. But his decision to stay came after much resistance from Kilborn’s previous staff, many of whom Stewart inherited.

Things eventually settled for Stewart after a while, as the show began to shed the “assholes” he’d inherited, although he would hang on to a few, including Stephen Colbert.

Indecision 2000 — Two years after he’d taken over from Kilborn, Jon Stewart had ditched many of Kilborn’s segments (though, he would hang on to “Your Moment of Zen.” Kilborn took “5 Questions” with him to The Late Late Show). Stewart had transformed the show from a character-driven fake news program to a news-driven fake news program. It was his coverage of the 2000 election and the election recount between George W. Bush and Al Gore, however, that elevated Jon Stewart to one of the leading voices in politics and journalism. In fact, the Indecision 2000 coverage would win The Daily Show the first of its Peabody Awards.

September 11, 2001 — While the election coverage established The Daily Show as one of — if not the — leading voice on television for politics, it was Jon Stewart’s first show after the 9/11 attacks that cemented Stewart as one of the leading voices in all of late-night television. It was in that September 20 monologue that Stewart truly became a trusted national figure.

The Crossfire Appearance — By the 2004 election, Jon Stewart had more than tripled the ratings of The Daily Show under Craig Kilborn to over a million viewers a night (it’s around 2.5 million now). In the midst of the 2004 presidential campaign, however, Jon Stewart appeared on CNN’s Crossfire and delivered such a withering attack on the Crossfire hosts for their brand of toxic, divisive punditry that he essentially took down the program. Stewart begged them, during the appearance, to “Stop hurting America.” Crossfire was cancelled three months later.

The Colbert Report — In 2005, The Daily Show launched its first spin-off, featuring Stephen Colbert. The Colbert Report would run after The Daily Show for nine years, until Colbert left to replace David Letterman on The Late Show (ironically, it was Jon Stewart who once had a holding contract to replace Letterman).

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The Writer’s Strike — In 2007, The Daily Show went on hiatus for two months during the writer’s strike, though it would return in 2008, more than a month before the writers returned. During this time, The Daily Show was called A Daily Show, and it was entirely ad-libbed. It also featured one of my favorite segments in the show’s history, where Stewart, Colbert, and Conan O’Brien all got into a fake fight (it was then that I realized — after years watching Leno and Letterman feud — that late-night rivals could actually like one another).

The Rally to Restore Sanity and/or Fear — In 2010, Jon Stewart and Stephen Colbert led a rally on the National Mall in Washington, D.C. that was attended by more than 215,000 people. The rally, which was designed to give a voice to those who didn’t represent the extreme views on either side of the political spectrum, managed to raise nearly $200,000 for charity and for a few minutes, at least, restore some sanity to the world.

Chaos on Bullsh*t Mountain — I don’t know that you could call it a turning point in the 2012 election, but the way that Jon Stewart ripped Fox News for covering the leaked Mitt Romney video certainly influenced public opinion and may have ultimately hurt Romney’s election chances.

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Stewart’s Leave of Absence — In the summer of 2013, Jon Stewart left The Daily Show for three months to direct Rosewater. That time away from the daily grind may have played a role in Stewart’s decision to ultimately retire from The Daily Show. Importantly, it also truly launched John Oliver’s career, leading to Oliver’s long-form news HBO program, Last Week Tonight, which has — in a way — taken The Daily Show to its next logical place.

February 10, 2015 — Jon Stewart announced that he would retire from The Daily Show after 16 incredible years as the host, selflessly making the decision to leave before the 2016 Presidential election campaign, which will no doubt put his eventual successor in prime position to help The Daily Show‘s continued success. As Stewart once told Craig Kilborn as a guest on The Daily Show the month before Stewart took over, he’s just a “monkey in the machine,” and while that is far, far from the truth, The Daily Show machine will certainly go on — for better or worse — without him.