Lisa Rogak - Angry Optimist

While busy acting, he also started to miss doing stand-up. “I think comedians have this Pavlov’s dog response when it comes to jokes,” Stewart said. “You tell a joke, you get a laugh—and I miss the immediacy of that. With a movie or a book, you have hours of wringing your hands, wondering if people thought it was funny.”

He was more of a natural in his occasional appearances on Dr. Katz, Professional Therapist , an animated show that ran on Comedy Central from 1995 to 1999, but that was only because the show revolved around comics performing their routines while sitting on a psychiatrist’s couch.

And then his most natural role appeared on the horizon in the form of The Larry Sanders Show on HBO, where he essentially played himself, a younger comedian who was being actively groomed and encouraged to replace an older mentor on a late-night talk show, played in the series by Garry Shandling.

Though he welcomed the steady gig, Stewart had misgivings about playing the role. “It’s really one of the most uncomfortable places you can be,” he said of his real-life predicament. “I think I realized I’d rather satirize who I am than be who I am.”

Stewart appeared on several seasons of the show from 1996 through the last episode in 1998, and along the way as Shandling-as-Sanders spoke about leaving the fictitious show on some of the episodes, Stewart’s character was rumored to step into the host’s shoes on the show. Though Stewart played himself on the show, he acknowledged that the show’s version of himself was rougher and ruder than how he presented himself on his own talk show on MTV and Paramount.

“But to play that character, I really couldn’t play myself. I needed the protection of the character to do the awful things the character would need to do.

“At first, I was playing me, but not well,” he said. “Then, in the last season, I got a full-blown story line and a chance to go outside myself. And to make it work, I really had to stretch.”

Instead of just showing up for a segment or two for a few episodes each season, since the network executive characters on the show were trying to push Sanders out while grooming Stewart to succeed him, the real Stewart not only had to spend more time on the set but he also had more lines. Lines that required him to act rather than just crack jokes, which was what most of his movie roles had consisted of so far. For instance, once Sanders and his producer Artie—played by veteran actor Rip Torn—got wind of the executives’ plans, several episodes revolved around the two backstabbing Stewart while they pretended that it was business as usual.

After his movie roles had gone nowhere Stewart started to sift through the deals he had made with both Miramax and Worldwide Pants. Though Miramax had broached the concept of a weekly sitcom, Stewart nixed it. “I was of the mind that, unless it was a great idea, I didn’t want to do it,” he said. “Just to do it for the sake of doing it wasn’t a good idea. No one needs another halfhearted attempt.”

With Letterman’s company, talk turned again to a late-night talk show to come after The Late Late Show with Tom Snyder . But he was hesitant to try to replicate what he had done previously. He was thinking of writing a book, and just didn’t want to tie himself down to another long-term television commitment. In the end both the Miramax and Worldwide Pants deals expired. Afterward, he went back on the road, on Comedy Central’s nationwide Stand Up for Sanity tour.

Stewart had found that he liked pursuing several different projects at the same time rather than having one full-time gig. “Admittedly, at some point I’m probably going to have to settle down and sort of pick a discipline and stay with it for a little bit of time, but right now it’s kind of nice to be able to float around and do a bunch of different things,” he said.

As a result, one magazine writer called him “the celebrity equivalent of lint: he pops up in interesting and unlikely places.”

There was also his growing discomfort in Los Angeles. A diehard New Yorker, he missed his girlfriend, Tracey. Their long-distance relationship had turned more serious. So he began to pull away from Hollywood with an eye toward returning to the East Coast.

The year 1998 would turn out to be a pivotal one for Stewart, and not just because he hosted a Sesame Street TV special called Elmopalooza, where he helped a variety of Muppets celebrate the thirtieth anniversary of Sesame Street .

For one, he was filming Big Daddy, a movie with hit potential that was shot in New York; it would hit theaters in June of 1999. When the project first came along, he didn’t think much of the part, or the movie, for that matter. But it did give him a chance to work alongside his old stand-up buddy Adam Sandler, who had come up in the clubs of New York at the same time.

“I always used to try to borrow money from Adam when he was making fifteen bucks a night,” said Stewart. “He was a soft touch.”

Stewart played the role of Kevin Gerrity, roommate to Sandler’s thirtysomething slacker Sonny Koufax. One day, Kevin surprises Sonny by dumping his five-year-old son at their apartment while Kevin flies to China for a business trip. Stewart turned the part from what could have been an extremely unsympathetic character into one with depth and wit.

“Jon had the trickiest part in the movie,” said director Dennis Dugan. “He’s in the first twelve minutes of the film and in that short amount of time, he has to make enough of an impression… so that when he returns at the end, they’ll go, ‘I’m so happy that this guy came back!’ And Jon achieved that.”

Also in 1998, Stewart put the finishing touches on his first book. Though some expressed surprise at his desire to become an author, to him writing a book that consisted of a collection of comic essays was very similar to writing a series of interrelated stand-up routines.

“I get the sense that it’s all the same thing, just in different forms,” he said. “I don’t look at it as that different.”

Naked Pictures of Famous People would hit the New York Times best-seller list when it was published in September. But a month before that, Stewart received even bigger news:

He actually appeared first on a list to take over a talk show. Not second.

His old guest-hosting position on Tom Snyder’s show was coming to an end: once Snyder announced his retirement, Letterman scouted around for a replacement. As usual, Stewart’s name appeared on the short list, but in the end, Letterman chose Craig Kilborn for the job. Kilborn, who was then hosting a Comedy Central show called The Daily Show, accepted the position. Yet again, Stewart was second banana. However, with Kilborn’s move the Daily Show spot had opened up.

“I always had my eye on [ The Daily Show ],” said Stewart. “But it’s kind of funny, it’s musical chairs. There are only five of these jobs available.”

Kilborn had hosted the show since the launch of the half-hour program, designed to “report” on news of the day by giving it a satirical twist. He’d cut his teeth as a sports anchor, first at a Fox station in Monterey, California, and then as an anchor on ESPN’s SportsCenter . Comedy Central had ordered The Daily Show into production to replace Bill Maher’s show Politically Incorrect , which had switched networks to ABC.