Jon Stewart Daily Show's most Stewart-esque moments: From squaring off with Chris Matthews to the 2013 government Shutstorm.

The Most Jon Stewart Moments in the History of The Daily Show With Jon Stewart

The Most Jon Stewart Moments in the History of The Daily Show With Jon Stewart

Brow Beat
Slate's Culture Blog
Aug. 6 2015 8:02 AM

The Most Jon Stewart Moments in the History of The Daily Show With Jon Stewart

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Jon Stewart.

Photo illustration by Lisa Larson-Walker. Photos by Getty and Reuters.

Many moments from Stewart’s Daily Show have already become cultural touchstones: his 9/11 monologue, his Jim Cramer smackdown, his rants about New York pizza. But which segments best capture the exact atmosphere and attitude of this Daily Show? As his time as host winds down on Thursday night, Slate staffers recall the most Stewart-esque moments from the past decade and a half. (There’s a reason so many of these moments are from 2004: If any political year felt custom-built for the Jon Stewart treatment, that was it.)

Playing straight man to Produce Pete, March 2003:

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Some of the greatest Stewart-era Daily Show correspondent bits were the “Produce Pete” segments in which Steve Carell played a local-newsish fruit-and-vegetable enthusiast whose segments inevitably culminated in his revealing some disturbing fact about his life as a deeply unhappy, divorced alcoholic who was unpopular with his co-workers. “A lot of people spend their summers vacationing with their family,” Produce Pete said during the segment on canning. “But I spend mine in the basement, putting things in jars!” Stewart was successful at the Daily Show in some part because he was so good as a collaborator and emcee/straight man, and to me those elements of his tenure are best represented by future megastar Steve Carell, in 2003, playing an idiot grocer who is despondently describing how he plans to make borscht for a mail-order Russian bride and her two brothers. –Slatest editor Ben Mathis-Lilley

Making Jennifer Love Hewitt uncomfortable, June 2004:

The first half, when Stewart and his guests do chitchat, shows how good he could be as a traditional talk-show host: quick, funny, aggressive, flirty, in control. Halfway through, the topic turns to Garfield: The Movie, the pointless 2004 live-action film Hewitt was there to promote—but Stewart has no interest in helping her promote it. He suggests that Bill Murray, who provided the eponymous cat’s voice, “must be some kind of crazy whore for money right now.” “This has been lovely, by the way,” Hewitt says near the end, with the look of a woman about to fire her publicist. —Gabriel Roth, Slate senior editor

Skewering Texas Republican Henry Bonilla, August 2004:

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In 2004, a GOP talking point brandished against John Kerry and John Edwards was that they were the No. 1 and No. 3 most liberal members of the Senate. While it was true that Kerry was a quite liberal senator, he was never really the MOST liberal, and Edwards was far from the third most liberal, but they were judged to be so because of weird quirks in the way the scores were determined by National Journal. I reported on it while covering the 2004 campaign; I also remember getting into it during a post-debate “spin room” session with John Cornyn when the Texas Republican repeated this “fact.” Though today this all must seem like unconscionable political pettiness, then it was one of those say-it-enough-it’ll-be-true charges that can never be killed. The rhetorically undead. Well, in this interview with Texas Republican Henry Bonilla, Jon Stewart takes the talking point doomed to walk the Earth, fashions it into a stake, and impales the undead. Charmingly. But relentlessly. As only Stewart could do. –The Gist host Mike Pesca

Also skewering Sen. Zell Miller, September 2004:

So much was farcical about the 2004 Bush-Kerry race, otherwise known as “Indecision 2004”—Kerry’s wind surfing, Bush’s words, and the way an election in midst of a disastrous war that we went into on false pretenses got turned into a referendum on Kerry’s Vietnam record. It was all perfect Daily Show fodder. Perhaps the most ridiculous moment of many, though, came after Democratic Sen. Zell Miller delivered a ferocious attack on Kerry during the Republican National Convention’s keynote speech. What happened next was an unhinged rant for the ages, one that seemed like it was designed to be taken down by Stewart’s trademark over-the-top impressions, razor wit, and perfect chyron puns. —Slate senior editor Jeremy Stahl

Squaring off with Chris Matthews, September 2004:

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The relationship between Jon Stewart and Chris Matthews wasn’t always so contentious—just look at this 2004 clip in which the two (mostly) commiserated about politicians being too afraid to answer actual questions. But a few years later, Matthews came on the show to promote his book Life’s a Campaign, and the spirit was considerably less friendly, as Stewart challenged what he deemed as the Hardball host’s “recipe for sadness.” The highlight: When an exasperated Matthews deems the moment “the worst interview I’ve ever had in my life,” as a nonplussed Stewart tries his best not to burst out laughing. It’s Stewart doing one of the things he does best—coolly and confidently winning an argument against an over-worked, bumbling guest. —Aisha Harris, Slate staff writer

Welcoming Steve Carell back to the show, August 2005:

In 2005, Carell returned as a guest to promote his first big movie, The 40-Year-Old Virgin. For the first few minutes of the interview, they sit in uncomfortable, theatrically awkward silence. Theatrically awkward happens to be one of the modes Carell works in best. But the best part is how well it showcases their rapport—it’s like watching two former bandmates sit down to play and realizing they still know the old songs. It’s funny and charming moment, even a little sweet. And it’s a great reminder of Stewart knack’s for cultivating, and then catapulting, talented comedians. —Panoply Web developer Paul Smith

On the media’s weird Sarah Palin coverage, September 2008:

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Sure, Stewart’s roll-clip-and-roll-eyes routine came to feel like a tic over time. But still: his Daily Show really did master the art of the media mashup—using deft cuts and curation to force talking heads to neatly debunk themselves. Not only does this 2008 segment on the media’s early coverage of Sarah Palin memorably describe as Karl Rove as “an analyst with a head like a lump of unbaked bread dough,” it also captures Stewart’s exact brand of cable-news parasitism. Here, with little more than some prime mugging and chin-stroking, Stewart takes apart a Rove rant about Palin and allows Bill O’Reilly to demonstrate his own inconsistent views regarding pregnant teens. The fact that it all feels, at this point, like boilerplate Stewart is why this clip is a classic. Slate senior editor Laura Bennett

Jezebel thinks I’m a sexist prick,” June 2010:

Stewart will be remembered as the face of progressivism in the early 2000s. And early 2000s progressivism looks pretty good! It’s funny, reliable, passionate, self-deprecating, white, male, and super super defensive about those last two things. Jon Stewart may be wittier and hotter and way more successful than the average brogressive, but when his commitment to race or gender equality are questioned, he reacts just as weirdly as any liberal Twitter rando. Former Daily Show writer Wyatt Cenac recently recounted what happened when Cenac, the only black writer in the room, advised Stewart against doubling down on a Herman Cain impression some saw as racist: Stewart allegedly stood up at the table and screamed obscenities at him. When the writer Alison Kinney attended a taping of The Daily Show in 2008 and asked Stewart in an open Q-and-A why his warm-up comic made ethnic jokes targeted at members of the crowd, she says he screamed and swore at her, too. This 2010 clip is classic Stewart, at his best and worst: In the middle of a delicious rant about the latest unhinged conservative talking point, Stewart veers off into a self-reflective fantasy, drops in a trite acknowledgment of a recent Jezebel report questioning the status of women on the show—“Jezebel thinks I’m a sexist prick!”—then returns to his regularly scheduled programming. A self-pitying throwaway joke in a fantasy sequence is as close as Stewart ever came to acknowledging the critics on the left. —Slate staff writer Amanda Hess

On the government “Shutstorm,” October 2013:

Stewart’s particular satirical formula is especially potent when aimed at hypocrisy, which was in ample supply during the two-week-long government shutdown of 2013—particularly in the bit that starts around 3:05 here. Exhibit A: Rep. Tim Walberg—a Republican from Michigan who called for the shutdown and later voted against ending it—bemoaning from the House floor the interruption of federal services. It seems Walberg was put out by the shuttering of the Panda Cam at the National Zoo. It’s a segment that capitalized on a particularly ridiculous, self-defeating moment in American politics and pinpointed exactly what made it so absurd. —Lexicon Valley podcast host Mike Vuolo

Read more in Slate about Jon Stewart:

Laura Bennett is Slate’s features director.

Amanda Hess is a David Carr fellow at the New York Times. Follow her on Twitter.

Aisha Harris is a Slate culture writer and host of the Slate podcast Represent.

Ben Mathis-Lilley is Slate’s chief news blogger. Follow the Slatest and Mathis-Lilley on Twitter.

Mike Pesca is the host of the Slate daily podcast The Gist. He also contributes reports and commentary to NPR.

Gabriel Roth is a Slate senior editor and the editorial director of Slate Plus. Follow him on Twitter

Paul Smith is an Emmy and Webby award-winning creative technologist with almost 20 years’ experience writing code for the web. Follow him on Twitter.

Jeremy Stahl is a Slate senior editor. You can follow him on Twitter.

Mike Vuolo is a radio and podcast producer and the host of Lexicon Valley.