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The many interesting ways Jon Stewart failed before ‘The Daily Show’

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Change is hard. For some of us — admittedly a niche audience — it was really hard in 1999 when the legendary Craig Kilborn left “The Daily Show” to replace Tom Snyder on “The Late Late Show,” taking his smooth-talking silliness with him. And they were going to replace him with. . . who?

The guy from MTV? Way to ruin a good thing, Comedy Central.

The joke was on us, of course. Viewership for “The Daily Show” skyrocketed as Stewart transformed the show from a funny-enough “Weekend Update”-meets-“Talk Soup” to a comedy juggernaut that steered the media-political conversation, spawned spin-offs and launched careers (Steve Carell, Ed Helms). “The Daily Show” was suddenly a new generation’s must-watch so popular that an older generation of people took notice, if only to wring their hands and ask: This is how our kids are getting their news?

But before Stewart became a late-night icon, he was just your run-of-the-mill stand-up comic, trying to find a toehold in the industry after a few false starts.

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Stewart moved to New York in the mid-80s after graduating from William & Mary to try to make it as a comedian. He was a regular at the Comedy Cellar and paid his dues doing late-night gigs for a couple of years before securing some television writing work and collaborating with the comedy troupe The State. Stewart slowly chugged along for years, getting gigs here and there, working on titles few will remember — “Caroline’s Comedy Hour,” “The Sweet Life” — until 1993, when it looked like Stewart might get tapped to replace David Letterman on NBC’s Late Show. Conan O’Brien got the job instead.

But the choice made sense. Stewart was too edgy for NBC, less goofy and huggable than Conan. Stewart needed a platform where he could dabble in darker humor at an hour when producers wouldn’t get too nervous. MTV was a perfect fit, with its younger audience and programming that included “Beavis and Butthead.” “The Jon Stewart Show” first aired in 1993. It was a 30-minute talk show with all the key ingredients you might find on network television — a monologue, musical guests, interviews, silly interludes — but with a hipper undercurrent.

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Watch a clip from 1993 and a few things are immediately clear. First, Stewart, who comes across as shifty and uncertain, hadn’t quite perfected his authoritative delivery. But even then, he was making jokes about political scandals (in this case Gennifer Flowers) that would be too risque for a big network show.

The show was a hit with Gen-Xers channel surfing late-night, and so naturally, the studio wanted more. But when Paramount tinkered with the blueprint, extending the show to an hour as a syndicated replacement for “The Arsenio Hall Show,” it tanked. The show was canceled in 1995.

So, what to do with Jon Stewart? He was really funny and he could act — plus, despite his foul mouth, he was kind of adorable. Could he be the lead in a romantic movie? Writer-director Willard Carroll thought so, casting Stewart as one part of a large ensemble in 1998’s “Playing by Heart,” a romantic drama that also featured Sean Connery and Angelina Jolie, of all people. Stewart played a unicorn of a love interest who, despite his perfection, had to relentlessly pursue a relationship-phobic Gillian Anderson. The movie was fine and Stewart was fine, but it was hard to imagine him having a career as the next Hugh Grant.

Besides, he was born to be an outlandish comedian. A slightly better fit was the bit part of the “enhancement smoker” he played in cult classic “Half Baked,” a guy who feels that everything, from staring at a $20 bill to watching a movie, is always more fun with a little marijuana.

“Did you ever see ‘Scent of a Woman’….on weeeed?” he asks his dealer. (Here’s the clip, though, warning, it contains a few bad words.)

Then he was utterly wasted as the straight man to Adam Sandler’s predictably Sandler-esque character in “Big Daddy.”

None of it was quite right. None of it played to his strengths. If there was one person who could predict what Stewart should do, it was comedian Denis Leary. In a 1994 New York Magazine story about Stewart, when “The Jon Stewart Show” was still alive and well, Leary said: “Jon’s shown more of his nice-guy side so far. . . As this show continues, it will get uglier; eventually it will just be this raging little Jewish man screaming into the camera.”

How prescient. Leary knew what five years later we’d all come to learn. Stewart was at his best when he was getting angry. Because the angrier he is, the funnier Stewart becomes. It’s a formula that has worked for 16 years and could probably work for 16 more.

But Stewart’s interests have expanded. If the last year has taught us anything, it’s that the enraged comedian can also be very serious. He directed “Rosewater,” a drama starring Gael Garcia Bernal about a kidnapped journalist. To make the movie, Stewart took a few months off from “The Daily Show,” letting John Oliver sub in. Maybe that was all Stewart needed to realize that he’d outgrown a job that once seemed tailored just for him.

Whatever he decides to do, which is still apparently up in the air, one thing is certain: “The Daily Show,” which existed before Stewart arrived, will live on after he leaves. Whenever Comedy Central chooses a replacement, people will no doubt be up in arms. There will be fear. There will be anger. That guy? we’ll wonder. (Or maybe even that woman?) But just give it time. Sometimes perfection is hard to spot until it yells in your face.


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