A Brief History of Jon Stewart’s Side Projects

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This week marks the release of Rosewater, Jon Stewart’s flawed but interesting feature filmmaking debut. As a serious-minded political thriller, it’s a bit of a departure for Stewart, who is primarily known as a talk-show host and stand-up comic — but his CV is more diverse than you might think. We took a look back at a few of his lesser-known (or, in some cases, all but forgotten) side projects.

Caroline’s Comedy Hour / The Sweet Life / Short Attention Span Theater

Stewart’s first TV gigs, landed when he was still a struggling young stand-up comic, were not as a host or performer, but a lowly writer. A&E’s Caroline’s Comedy Hour, a stand-up showcase taped at NYC’s famed comedy club, was a favorite for all of us late-‘80s comedy nerds (you know who you are); Stewart got his first credits as head writer for that program, which presumably meant penning the intros and host patter and the like. From there, he got a writing job on The Sweet Life, a sketch and talk show starring singer Rachel Sweet. It aired on The Comedy Channel, one of two cable networks that launched simultaneously in 1989 with all-comedy formats. A year later, the two channels merged to form Comedy Central (which would later play a key role in Stewart’s career); before that happened, Stewart made his first on-camera appearances, first in Sweet Life sketches and then as host of the compilation show Short Attention Span Theater (which would make the transition to Comedy Central).

You Wrote It, You Watch It

When the Comedy Channel merged with HA!, it came under the purview of MTV, which quickly went to work making Stewart into a network personality. It would have some success with The Jon Stewart Show, his first major showcase, but before that came You Wrote It, You Watch It, one of the lowlights of the network’s ‘90s programming (and that’s saying something). The premise was this: viewers would send in stories from their daily lives, which Stewart would then turn over to a sketch troupe to act out. The host did his best, as did the sketch players — a little crew called The State — but neither could rise above the premise, and the show was canceled after 13 weeks. But it led to better things; both Stewart and The State landed their own MTV series shortly thereafter.

George Carlin: 40 Years of Comedy

The Jon Stewart Show had a respectable run at MTV, only to tank when corporate overlords Viacom attempted to remake it into a syndicated series, filling the hole left by the end of their Arsenio Hall Show. In the years that followed, Stewart honed his stand-up (culminating in a special, Unleavened), signed a development deal with David Letterman’s Worldwide Pants, and moderated this 1997 special honoring one of his comic idols, George Carlin. The special is a mash-up of new material, clips, and a Stewart-Carlin interview; in the latter, Stewart displays his knowledge and passion for Carlin’s work, and provides an early example of the comedians-talking-shop format that would dominate the current podcast landscape.

The Late Late Show With Tom Snyder

As part of the Letterman deal, Stewart would frequently sit in as guest host for The Late Show With David Letterman’s lead-out, The Late Late Show With Tom Snyder (also produced under the Worldwide Pants banner). His Daily Show interviews are hit and miss — for every riveting O’Reilly or Jim Cramer conversation, there are two or three phoned-in movie star chats — but he flourished in this low-key, lengthy format. In fact, he fit in so comfortably that there was serious talk of Stewart taking over the slot when Snyder retired in 1999. Alas, the job went to Craig Kilborn, but all was not lost; to take the gig, Kilborn vacated The Daily Show, which became infinitely better after his tenure. (Subsequently, The Late Late Show become infinitely better after his tenure there. We look forward to the next show that he exits.)

The Larry Sanders Show

Garry Shandling’s savvy, brainy, and brilliant satire of the entertainment industry in general and late-night talk shows in particular debuted in 1992, right around the much-reported “war” between Leno and Letterman for The Tonight Show (and the subsequent bumper crop of competitors, sniffing blood in the water). Over the course of its run, it would continue to mirror developments in the industry — so as Stewart was circling the Snyder show, he was added to the Sanders recurring cast as himself, being courted by Larry Sanders’ network as a younger, hipper replacement for the aging host. Stewart appeared in several memorable episodes; the best, “Adolf Hankler,” showed “Jon Stewart” struggling with the woes of doing a hip show without running afoul of network standards and practices, who are inflamed by a Nazi sketch and his choice for musical guests (above).

Playing By Heart / Death to Smoochy

There was a time, shortly before his version of The Daily Show took off, when the idea of Stewart as a movie star seemed not only possible, but inevitable. In the mid-1990s, he (via his Busboy Productions shingle) signed a development deal with Miramax Pictures, to develop and appear in films for the indie studio. He did four films for them; the most interesting was the Magnolia-lite ensemble romantic comedy/drama Playing By Heart, an uneven but likable picture in which Stewart quite convincingly plays romantic leading man (opposite Gillian Anderson, also very good). The notion of Stewart juggling TV and movie stardom pretty much came to an end with the loud failure of Death to Smoochy, in which he played a key supporting role, but it must be said — for all of the criticism of the film (most of it coming from Stewart himself), he’s not half bad in the movie, and it has, in recent years, been championed by cult film lovers as a misunderstood but ultimately successful dark comedy.

Naked Pictures of Famous People

Stewart’s two books penned with the Daily Show staff, America (The Book) and Earth (The Book), were critical success and huge sellers, but his finest achievement as a writer arrived a year before he began his Daily Show tenure. Naked Pictures is a collection of satirical essays, firmly in the mold of Woody Allen’s early books (like Getting Even and Without Feathers). Every damn piece is funny, but the highlights are “A Very Hanson Christmas” (a series of increasingly depressing Christmas letters from the matriarch of the “MMMBop” clan), “The Recipe” (a scathingly on-target “recipe” for how to put together an awards show — which Stewart would soon learn more about firsthand), “Martha Stewart’s Vagina” (advice on a very personal bit of decorating), and “Adolf Hitler: The Larry King Interview” (which you can probably figure out yourself; hear Stewart and radio host Mike O’Meara perform it above).

25 Lame

Just a few months after taking over The Daily Show, Stewart appeared on this one-off MTV special alongside Chris Kattan and old pals Janeane Garafalo and Denis Leary. The premise was simple: MTV viewers voted on the 25 worst videos in history, with the top ten airing for the last time ever (they said) on the network. The special entered MTV lore for the freak-out, set-smashing special appearance of Vanilla Ice (whose “Ice Ice Baby” was number nine on the list), but that wasn’t what made the show great — it was the opportunity to see four (OK, three; sorry, Kattan) very funny people popping up to riff on the videos, MST3K-style.

Three Strikes

Stewart’s deal with Comedy Central included an opportunity to develop other shows for the network via his Busboy Productions. Most have been, at their essence, Daily Show spinoffs: The Colbert Report, Important Things With Demetri Martin, the forthcoming Minority Report With Larry Wilmore. But in 2006, the company (and executive producer Stewart) produced a pilot called Three Strikes. Written by Alex Gregory and Peter Huyck (alums of Larry Sanders and several other series), it was set in the world of minor-league baseball. Yet Comedy Central passed on the pilot, and attempts to place it at other networks were unsuccessful, though it ultimately made its way online.

Sportsfan / The Naturalized

Busboy has had greater success as a producer of documentaries, with two TV docs to date executive-produced by Stewart — and reflecting his interests. He’s known for his sports fandom (particularly via the ongoing frustration provided by his beloved Mets), and in 2006, SpikeTV aired Sportsfan, director Aaron Lubarsky’s chronicle of one season with the Minnesota Vikings, as experienced by a group of their diehards. And in 2010, History aired The Naturalized, also by Lubarsky, concerning the quest for citizenship as seen through the eyes of several would-be immigrants. In other words, it’s a serious movie about an important issue — so maybe Rosewater wasn’t such a stretch after all.