by Lisa Rogak
He also served as executive producer of the new version of the show, and he regularly skirmished with those from the executive suite. “When it comes down to content, that’s where I choose my battles,” he said. “If they say, well, we’d love it if you’d wear a black sweater tonight, I’ll usually do that, but if they say, well we don’t think that bit’s funny, we don’t want you to run it, I say, ‘Well, we do,’ so we put it on.”
Also, filling one hour was a lot harder than just gabbing with minor and frequently unknown guests while occasionally punctuating a question by hurling a puck around the Nok Hockey table. Syndication also meant that individual stations decided when to air the show, and in some markets the only time they deemed to be available was three in the morning, which made it difficult to build an audience.
The stress and hours were beginning to take their toll. He was responsible for people, whereas with him doing stand-up, he only had himself to worry about. “The first four or five weeks, it was like every episode was Broadcast News. Ten seconds before it went on, somebody was sprinting down a hallway with the fat-guy tape,” he said. But after the first month, he and the rest of the staff finally fell into a comfortable rhythm.
“We have to get comfortable with not running as fast as we can,” he said. “I think it’ll help the show actually. There were a lot of times on MTV when I thought we gave our guests short shrift and now we won’t have to. We just have to find the balance between short shrift and ‘OK, that’s enough, we get it.’
“A guy brought trained condors and one flew out in the audience, and we stood there dumbstruck while it bit an audience member’s back,” he said. “I was staring at this huge bird gawking in the audience while the trainer says, ‘Hey, man, maybe you should go to commercial.’ And I said, ‘Hey, maybe you should get your bird.’ The next night, Marilyn Manson was on and they ended up lighting the stage on fire. I really thought somebody was going to be killed that week.”
Even though he and the staff adjusted, the audience in many cases didn’t. “People did get used to our half-hour pacing, so when they watch it now, they think, ‘Hey, this is supposed to be over! Make him stop!’” And even he had trouble with the hour-long format. “There are times when I’ll just be sitting out there, thinking about my laundry.
“Trying to make a talk show compelling is the most difficult thing in the world,” he said.
The pressure continued to build as the ratings dropped. What was worse was that in markets where the show aired in late-night prime time—at 11:30—he was up against not only Letterman, his hero, but also Jay Leno and The Tonight Show.
“Doing this gig is like when you see pictures of the presidents when they first get into office, and then two years later they look like shit,” he said. “That’s what’s going to happen to me.”
He also realized a surprising thing: with all of its hassles and risks, he actually missed performing live in front of an audience by himself. “One of the nice things about stand-up is you work on material” … and “give it time to breathe and live,” he said. “When you’re doing a monologue [on TV] every day, rather than discussing things that matter, it’s, ‘Hey … a guy fell into a vat of macaroni. [W]e can do something with that!… You start to lose sight of what you actually think.”
Paramount pulled the plug and the last show aired on June 23, 1995. That day, Stewart and the production crew passed out margaritas to members of the audience and paid for their cab rides home.
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“When it ended, I was blown out and exhausted, emotionally raw.”
Stewart decided to take a few weeks off. However, unlike many New Yorkers in the entertainment business, he thoroughly disdained the chic summer getaway of the Hamptons. “The Hamptons are the most Hollywood place in New York, filled with all the people in New York you’re trying to avoid,” he said.
Instead, he retreated to his beloved Jersey shore. “You go down to the Jersey shore, lick your wounds for two weeks, and come back kicking,” he said. “You can’t just fold up the tents, you’ve got to refocus yourself and get back in it.”
It was clear that doing the show had helped him to grow up, a lot. “When the show got canceled, I still knew how to write jokes the next day,” he said. “That was a huge revelation. Because at first you think, ‘I won’t have any shelter! What am I gonna do?’
“I shed a lot of the bullshit, the neuroses of earlier years. I still have my moments of abject panic, but I’ve been able to control it more as I’ve gotten older.”
His mentor also gave him a few words of wisdom after the show ended. “Letterman said something that stayed with me: ‘Never confuse cancellation with failure.’”
“As long as I don’t end up hosting a skin care commercial with Cher, I’m happy,” Stewart joked.
He returned to New York, refreshed and ready to make plans, when he was thrown for a loop: a month after the show was canceled, something even bigger happened than landing another show: he met the woman he’d end up marrying.
Though neither Stewart nor Tracey McShane, a veterinary assistant, had been on a blind date before, they arranged to meet at a Mexican restaurant after getting fixed up by one of Tracey’s friends. And it almost didn’t happen.
McShane had recently ended a long-term relationship and she didn’t hold out much hope that she’d meet someone new, even though her friends were constantly playing matchmaker for her. Because her roommate worked in the entertainment business, she had been set up with a number of actors; unfortunately, the dates always bombed. Even though McShane had told her roommate, “No more performers,” she had once mentioned that she would like to go out with someone like the host of a talk show that had just been canceled because she thought he was “funny and sweet.”
With his schedule freed up, and because he was starting to entertain offers for acting jobs from Hollywood, he started to frequent movie sets in Manhattan, where he met McShane’s roommate. One thing led to another, and the two arranged to meet. The initial reaction didn’t go well.
They agreed to meet again, and within a few weeks they were inseparable.
CHAPTER 5
WITH HIS SCHEDULE changed from working seventy-hour weeks to zero, Stewart finally had a chance to think about what he really wanted to do. He decided to take his time figuring it out. He toured the country performing stand-up at the kinds of hole-in-the-wall comedy clubs that he had appeared at before he hit the big time. He also started to sift through the increasing number of offers that came in, ranging from movie deals to subbing for talk-show host Tom Snyder, who was at the helm of The Late Late Show.
Despite his new relationship with McShane, he decided to move to Los Angeles in order to develop these new opportunities, though he was understandably reluctant about leaving the New York area, where he had spent his entire life aside from college. He liked the fact that for the most part, New Yorkers didn’t much care about celebrities.
“Everybody’s got their own shit to worry about,” he said. “I think that as long as I keep the music down, they’re fine.”
But sooner or later, Hollywood beckons many New York–based comedians and actors, and Stewart was no exception. And when Snyder offered him the chance to occasionally substitute for him on his late-night show, Stewart decided to head west.
Snyder was a veteran talk-show host who had hosted Tomorrow with Tom Snyder from 1973 through 1982. With his background in hard news, the show had an inquisitive, thoughtful style, though his pointed questions were also interspersed with Snyder’s opinions and comments; it was almost like watching two people hold court in a living room, punctuated with occasional sparring. Then, after more than a decade away from sitting behind a talk-show desk, Snyder had signed on to The Late Late Show in 1995, which was launched by David Letterman’s production company Worldwide Pants as a way to hold on to viewers after his own show ended at 12:35 A.M. The irreverent Snyder was a great choice for that time slot and he would helm the show until the spring of 1999
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Stewart first sat in for Tom Snyder in the fall of 1996, and did so well that he became a regular substitute host, filling in every three or four months, usually for a week at a time. The difference in height between the two hosts—Snyder was six four to Stewart’s five seven—provided for some memorable moments.
“The cameras [and furniture] were designed for his frame, so when I got there I looked like [Lily Tomlin’s] Edith Ann character sitting in the chair,” said Stewart. “They had to give me a booster cushion. So whenever I was working that show, I was actually sitting on a children’s pillow.”
And he sometimes acted like a kid, breaking into The Price Is Right studio with his friends after hours, where they took turns spinning the big wheel that served as the cornerstone of the game show.
Yet he felt like he could never totally relax and be himself while guest hosting. “When I was doing The Late Late Show with Tom Snyder, it was like house-sitting. So while it’s nice, because it’s a nice place to house-sit, you’re still a little worried like, ‘Oh my God, I just got ashes on the couch. Now what am I going to do?’ You don’t want to be the guy to fuck it up for when the other guy comes back and goes, ‘Who drank all my whiskey?’”
Even though it was common knowledge that Snyder wouldn’t stay on more than a few years because he wanted to retire, and some speculated that Stewart would make an ideal replacement, Stewart let it be known that it wasn’t in the cards. He was hesitant to commit to another talk show so soon after the failure of The Jon Stewart Show at Paramount.
He took advantage of being in Los Angeles to branch out in his entertainment career. And just like after all the odd jobs he held after college, Stewart figured he might as well try everything. He hit the ground running, and then some.
He signed a deal with Miramax Films with his recently launched Busboy Productions company, which he named for one of the many part-time jobs he had held through the years. The pact committed Stewart to star in at least two film projects per year and offered him the chance to write and produce as well.
And even though he said he’d never do a syndicated show again, Stewart also signed a development deal with Letterman’s Worldwide Pants company to eventually host and produce his own late-night talk show, one which would be totally on his terms where he wouldn’t have to kowtow to a large entertainment company’s executive brass.
It didn’t take long before Stewart picked up small roles in popular TV shows like The Nanny and NewsRadio, and taped a couple of live stand-up performances that were later broadcast by HBO, including Jon Stewart: Unleavened. He also appeared in a number of small parts in movies where he appeared alongside some of the biggest stars of the time.
He thought his first big break would come in the 1996 movie The First Wives Club playing opposite Goldie Hawn, but his scenes ended up being deleted from the film. He followed that up with a role opposite Drew Barrymore in the romantic comedy Wishful Thinking, which also came out in 1996. The story was told by jumping between several different points of view—including Barrymore’s and Jennifer Beals’s, the other female lead—and turned mixed and missed signals into well-trodden jokes. Stewart played a nebbishy third or fourth wheel who in the end became Beals’s love interest. To no one’s surprise, least of all Stewart’s, the film went straight to video.
Half Baked came next, where Stewart had a cameo role—billed as “Enhancement Smoker” in the end credits—of the cult stoner movie starring Dave Chappelle. The movie is about a group of pot-smoking friends who have to come up with the money to bail a buddy out of jail after he accidentally kills a diabetic police horse by feeding it junk food. Reviewers regarded it as the ultimate pothead film. Stewart followed up that role with another small part in Since You’ve Been Gone, a made-for-TV movie starring David Schwimmer about a disillusioned group of friends attending their tenth high school reunion.
Next up was the romantic comedy Playing by Heart—the original title was Dancing about Architecture—which featured a series of interlocking stories and a top-notch cast, including Sean Connery, Angelina Jolie, and Gillian Anderson. Here, Stewart’s role was a bit meatier, as he played an architect named Trent intent on courting Anderson’s man-shy character.
Jon Stewart and Drew Barrymore at the premiere of Wishful Thinking in November 1995. (Courtesy REX USA/Rex)
In all of his roles, Stewart’s lack of acting chops was evident. It wasn’t until he got the chance to play a different kind of role in the 1998 movie The Faculty, a flick about a group of high school students attempting to stave off an alien invasion, that it appeared he finally loosened up and looked like he was enjoying himself. Stewart played a biology teacher named Professor Edward Furlong who along with fellow actors Salma Hayek, Bebe Neuwirth, and Usher, of all people, is transformed into an alien after being infected with worms from space. One reviewer advised viewers to “Think of it as Invasion of the Body Snatchers enacted by the cast of Scream, an enjoyably dumb B movie.”
Stewart and actress Gillian Anderson, his co-star, in a still from the 1998 movie Playing by Heart. (Courtesy REX USA/Moviestore Collection/Rex)
Stewart’s performance in all of these movies was unremarkable, a fact that he fully recognized. “The truth is, I’m not a good actor, but it’s fun to try,” he admitted.
“I trusted these people. I was hoping that they knew what I could do, and that was okay with them. I didn’t go from being a talk-show host to being Sean Penn, I just went to being in a movie. I really felt like I didn’t mess up, but I am really proud of it because I feel that I didn’t mess up. I wasn’t the burnt kernel in the popcorn. In that sense, I felt really proud of it that I held my own in this situation.
“[A]ll you can do is show up on the set,… and hope it works out. And then you go home and write your own stuff.”
Some felt that Stewart’s background as a stand-up comedian hurt his chances at succeeding in the movies. “While it’s something that a lot of comics try to do, it’s really hard to be able to play a role when people look at you and think of you as yourself,” said Joey Bartolomeo, a senior writer at US Weekly. “If you look at someone like Jerry Seinfeld, his only role has been as Jerry Seinfeld on TV. You don’t see him in movies playing other parts.”
At the same time, Stewart credited his talk-show experience with helping his acting more than doing stand-up. “When you do stand-up, so often you’re the only person on stage and it’s all your thing,” he said. “It’s very gladiatorial. Obviously, when you’re in a scene with somebody, you’re supposed to listen and react—and that’s a bit of a transition.”
“As a stand-up comic, you don’t work with other people,” he noted. “As host, you’re hanging on to every word people say because you have to react to it.”
“It’s nerve-racking to be with people who know how to act,” he added. “Most comedians are doing themselves, ten percent angrier or happier. I like being able to do a little stand-up and do something else and also try acting. It’s that neurotic vision: the more things that I can do, the more employable I’ll be in the future.”
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 misg
ivings 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.”