25 Years After Joining ‘The Daily Show’, Could Jon Stewart Win Another Late-Night Emmy?

Peter White
·5 min read
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January 11, 1999, 25 years ago to the day, was Jon Stewart’s first night hosting The Daily Show.

The comedian took over from Craig Kilborn, who had hosted the Comedy Central show from July 21, 1996. Stewart’s first guest was Michael J. Fox, promoting Spin City.

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The Daily Show with Jon Stewart went on to win the Emmy for Outstanding Variety Series for ten consecutive years between 2003 and 2012, before losing to The Colbert Report, a show that he exec produced, for a couple of years, and then coming back to win in 2015 in his final season.

It’s a run that Last Week Tonight with John Oliver looked like it might replicate with seven wins in the category – then known as Outstanding Variety Talk Series – starting in 2016.

However, Oliver is now competing on Monday night at the primetime Emmys in a new category, Outstanding Scripted Variety Series, up against Saturday Night Live and A Black Lady Sketch Show, while Stewart is back in the Emmy race – for Outstanding Talk Series – with The Problem with Jon Stewart.

Could Stewart win another late-night Emmy next week?

He’s up against The Late Show with Stephen Colbert, another interesting battle between two old friends, as well as his old show, The Daily Show, competing with Trevor Noah’s final season. Elsewhere, Jimmy Kimmel Live! and Late Night with Seth Meyers are also in the mix.

Stewart’s show was axed in October, reportedly due to creative differences between him and his team and Apple, which was thought to be worried about his take on issues such as China and A.I, a move that prompted members of a special House committee to fire off a letter to Apple, questioning whether the decision to end The Problem with Jon Stewart was due to concerns over the company’s relationship with China.

However, that will have very little impact on the Emmys race as the voting window was in August, before that news came out, and a few months after season two of The Problem with Jon Stewart aired.

Regardless, The Late Show is the odds-on favorite to win on Monday, with Colbert’s old Daily Show correspondent partner Oliver now out of the picture, but some suspect Jimmy Kimmel Live! could also nab the top prize. Kimmel is a popular figure among awards voters and is seen as someone who plays the game nicely, hosting the Oscars, for instance, but can crack an acerbic, inside joke about the industry.

Noah, who left well over a year ago and has yet to be permanently replaced at The Daily Show, and Meyers feel like outsiders, but it is also hard to judge given Oliver’s run of wins.

JON STEWART: 25 YEARS ON

The timing of it all is interesting for Stewart, half a century on from essentially shaking up the late-night universe.

He had previously hosted The Jon Stewart Show, initially as a 30-minute show for MTV and then in syndication for an hour-long show but it was canceled and ended in 1995.

Stewart then went on to appear in a few movies including Dave Chappelle’s Half Baked, Playing By Heart and Wishful Thinking, hosting a short-lived talk show in the UK for the BBC called Where’s Elvis This Week? before recurring as a talk show host on The Larry Sanders Show.

Then Craig Kilborn left The Daily Show to replace Tom Snyder on The Late Late Show, leading to Stewart taking over, persuaded by Doug Herzog and Eileen Katz at MTV and exec producer Madeleine Smithberg.

“I was relatively cool on the idea,” Stewart said in The Daily Show (The Book): An Oral History. “My last foray in the real world of television hosting (fake hosting with Larry Sanders not withstanding) had ended with my face on a dartboard in the New York Post with the headline ‘Stewart Joins Late Night Losers’. That’ll leave a mark.”

But he took the job, he said, thanks to his wife Tracey.

“I definitely advocated for him to do it,” added his manager James ‘Babydoll’ Dixon in the book. “I just said to him, ‘You can put this through your prism. You can make it smarter and different than what it’s been’. Now, I definitely didn’t see the show becoming the political lightning rod that it evolved into.”

His first joke on January 11, 1999 was that Kilborn was on “assignment in Kuala Lumpur” and his first headline was ‘The Final Blow’ about President Bill Clinton’s impeachment trial in the Senate.

But things weren’t particularly smooth at the start with Stewart ruffling feathers with some of the Kilborn writers. Jen Flanz, who started as a production assistant and is now the showrunner and exec producer, said, “It didn’t necessarily feel like Jon was in charge right when he got there. When Ben [Karlin] came in, that felt like more of a shift in the universe.”

But it all worked out and Stewart ended on The Daily Show on August 6, 2015.

“My wildest dream for The Daily Show when I started was, ‘This will be fun. Hopefully we’ll do it well.’ Success for me wouldn’t been feeling like I figured it out. That I got to express the things I wanted to. It was never ‘I want this to be a cultural touchstone… but only for a very small portion of America’. And I was hoping to stay on TV longer than nine months this time.”

Stewart certainly did that.

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