Can Jon Stewart’s New Apple Series Outrun the Shadow of ‘The Daily Show’?

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“What he’s up against is competing with his old legacy,” Syracuse professor Bob Thompson says


Jon Stewart’s celebrated run as host of Comedy Central’s “The Daily Show” birthed the current politically charged late-night TV landscape. Now he’s competing against his own legacy.

On Thursday, Stewart launches “The Problem With Jon Stewart,” a biweekly current event series for Apple TV+ that promises to be much more serious and thought-provoking than what viewers may remember from the former late-night host. Each episode will focus on a single issue, which will then be expanded upon further in a companion podcast.

But the question remains: Can Stewart ever escape the domineering shadow of his culture-defining, award-winning, 17-year run on “The Daily Show?”

“What he’s up against is competing with his old legacy. And by that I mean the legacy of all the other people who took Jon Stewart’s style and ran with it,” Syracuse professor and media historian Robert Thompson told TheWrap. “What Jon Stewart begat is going to be his biggest competition.”

Stewart is largely credited with upending the late night world and pushing it from the mostly apolitical days of Johnny Carson and Jay Leno into the current world where every single commentator in the late night sphere has to have some kind of political opinion — or be punished in the ratings if they don’t.

“‘The Daily Show’ has had more influence on late night than anybody else has,” Robert Smigel, a longtime comedy writer for “Saturday Night Live” and the early days of Conan O’Brien’s “Late Night” run, told TheWrap back in June. After Stewart took over from Craig Kilborn as host in 1999, the Comedy Central series helped to redefine the late-night genre by “combining news and entertainment and people really getting their news from these comedy shows and forming opinions from them, or having their opinions reinforced.”

A look at the current crop of shows includes three that built their fame alongside Stewart on “The Daily Show”: John Oliver (who won his sixth consecutive Emmy for Outstanding Variety Talk Series for his weekly HBO series “Last Week Tonight”), Samantha Bee and Stephen Colbert.

“He changed so much in late night, and so many people then took a page from his book and went out and ran with it, including so many of those people that were on ‘The Daily Show,’” Thompson said. “He got that all started, and now he seems a lot more old-fashioned.”

Stewart has kept a low profile since signing off from “The Daily Show” in 2015, save for the occasional appearance on Colbert’s “Late Show” or his work writing and directing the 2020 political comedy “Irresistible,” which got middling reviews and bypassed theaters for an on-demand release. He was more successful arguing on behalf of 9/11 first responders during a 2019 Congressional hearing. (The Senate would eventually renew the 9/11 Victim Compensation Fund for the next 70 years).

Stewart, who declined to be interviewed for this story, has explained his decision to come back to television — on his own terms. “It was thinking about the parts of working on ‘The Daily Show’ that I found frustrating. We spent so much time trying to fend off the day-to-day that we didn’t have that much of a chance to sit back and have a more considered analysis,” Stewart told the New York Times Wednesday. “The ‘Daily Show’ process was relatively eccentric. It’s ephemeral and I love the forgiving nature of that: You go in on a Tuesday show and miss all your marks, but then there’s always Wednesday and there’s Thursday. There’s other parts that can be less satisfying.”

Stewart added that he’s aware of the current late-night landscape is not only more crowded than ever but looks a lot like it’s playing his own greatest hits.

“If you begin to view what you make as a function of external processes — whether it’s other shows that traffic in a similar sensibility, or internet commentary or expectations — I think you can’t win,” Stewart told the Times. “Because you won’t create something that’s authentic. Imagine saying to someone who plays guitar, ‘Lotta guitarists out there, man.’”

And it remains to be seen exactly what Stewart has in mind for “The Problem” — especially since he’s tapped “CBS Evening News” veteran Brinda Adhikari as his showrunner and “Daily Show” alum Chelsea Devantez as head writer.

Thompson fears that Stewart can’t hit the same high notes on “The Problem” as he did with “The Daily Show,” but that’s only because his first act was so successful.

“He is in the pantheon of some of the most, not only influential people in American television, but also in the political, the American conversation,” Thompson said. “His best work has been done. He totally transformed late night, he totally transformed the political conversation. I go so far as to say he almost invented serious TV satire. Johnny Carson told jokes about politics, but he was far from a political satirist.”