Angry Optimist: The Life and Times of Jon Stewart

CHAPTER 4

WHEN THE JON STEWART SHOW debuted on MTV on October 25, 1993, it was entering an already crowded field. Just as the market for stand-up comedy was growing when Stewart first entered the fray, when his half-hour show launched, it was part of a talk-show boom that was going on, with actors including Ricki Lake, Chevy Chase, Vicki Lawrence, and Arsenio Hall all offered their own shows.

“There are four other talk shows battling it out out there, and we think Jon is the best shot we can take in that environment,” said Doug Herzog, who served as president of MTV Productions at the time. “Plus, Jon has that MTV attitude. He has a hip, skewed way of looking at things and, even though he can act like a wise guy, he’s also very sweet.”

Both Stewart and MTV executives knew they were going after an audience that was different from the other mainstream network talk shows that were hitting the air at the time, and to clinch the deal, the network scheduled his show to come right after Beavis and Butt-Head, an animated series starring two teenage miscreants whose favorite activity was to sit on a couch while watching music videos and make typically teenage comments about them. From the time the first episode aired in the spring of 1993, the cartoon was a hit, garnering a large audience of teenagers and twentysomethings, the target audience for Stewart’s show.

“This show is a little bit more seat-of-the-pants than what people are used to seeing on network television,” said Stewart. “Anything unpredictable is usually miraculous and much better than what you could have planned.”

“Imagine if you sit there and you’ve seen three morons in one hour: Beavis, Butt-head and me.”

“We didn’t sit around wondering, ‘How do we make a Generation X talk show?’ It just represents my sense of humor,” said Stewart. “How I am on the show is how I am, except, of course, that I’m miked.”

One look at the set and it was clear this wasn’t a typical talk show of the early 1990s. The stage set looked like it came from the back of a grubby auto mechanic’s garage, while the several black-light panels serving as backdrops were nice touches in keeping with the overall industrial theme. Stewart used a wooden tabletop hockey rink—known as Nok Hockey—for his desk, and guests perched on the front seat of an old car that had been pulled from a junkyard.

“We’re a little more casual than some of the other programs,” he added. “The pressure isn’t as harsh. People can check in and hang around. Other shows are very much in a war. We still have that annoying puppy-type quality of just being happy to be here.”

He also realized that if the program was on a more widely watched network, then he would be running a very different show. “If we were doing the show on network, we’d probably have to rein it in a little bit. We can be rougher and it doesn’t appear out of place because of the context of the channel we’re on.”

Case in point was when model Cindy Crawford appeared on the show. After he told her she had very soft skin, she pulled a vial of skin cream from her purse and proceeded to apply it to the top of his hand. When she asked him if it felt good, he replied, “I don’t know, Cindy, when I have cream on my hands, it’s usually on the other side.”

In any case, he admitted he preferred being on MTV because he wasn’t required to put on airs. “The way I dress on the show, that’s what I like, that’s how I live, except the show is cleaner,” he said. “If it were really my life, it would be me and the guest and a pile of dirty laundry next to us. And some cat litter that needs to be changed.”

Improbably, given the juvenile lead-in show, MTV believed Stewart would be able to attract a female audience to the show. “Women will love him as well, which is important because we see this as having broad appeal,” said Herzog. “He’s perfect for MTV without being too MTV.”

“We were an aberration on MTV,” said Stewart. “We actually talked to people seven minutes at a time.”

The cable channel committed to twenty-four episodes, and Howard Stern was the first guest. His book Private Parts had just been published and he was booked on the show to promote it. Stewart was a big fan and he spent hours planning his responses to every possible retort. But the interview didn’t get off to a great start.

“I don’t know who you are and you’re going to be off the air in six weeks,” said Stern. He then proceeded to criticize Stewart while the brand-new talk-show host tried valiantly to hide his shock. “Howard was just nailing me left and right, so I did the only thing I could do. I just flipped open his book and I go, ‘What’s this chapter on lesbians?’ Woo. He was off me.”

With Conan O’Brien making his debut on NBC around the same time, it was natural for critics to compare the two shows. By and large, they preferred Stewart’s approach and style as more refreshing.

“Conan’s show was billed as the voice of Generation X, so there was that expectation, but I don’t think he cuts it,” said Entertainment Weekly TV critic Bruce Fretts. “Conan’s show feels so forced, like they’re trying so hard to be hip and ironic.”

And compared with the other talk-show competitors at the time, Stewart’s show stood out for its length: it was thirty minutes while the others were an hour or more. “The whole point [is] that even when it sucks, it’s only a half-hour,” said Stewart. “So come on, they can sit through that. If they can sit through a half-hour of a Flowbee commercial, they can certainly sit through a half-hour of my show.”

From the start, the bulk of guests were bands with music videos currently on heavy rotation on MTV, which made sense given who was footing the bill. “It was important to get people the MTV audience recognized.” But at least Stewart had a passing familiarity with the bands and so could hold a halfway interesting conversation with guests.

“The bands we have on the show play the music I listen to,” he said, but as for the nonmusical guests, given that he was on a cable channel with little to no budget, he essentially had to book B- and C-level stars who were already in New York. “The guests are more of a potluck of who’s in town,” he said. “Letterman sits down to feast, and then we ask, ‘Are you gonna finish that?’”

That said, some higher-caliber celebrities did appear on the show from time to time. Both Cindy Crawford and William Shatner visited and Stewart made an effort to convince some of the stars from The Brady Bunch to come on the show. But he quickly learned that the best approach to the show was to essentially wing it, instead of scheduling it down to the second.

“You can’t plan this kind of show in advance,” he said. “We spent four months designing the show, and the first week we were on the air it was evident that seventy-five percent of the stuff we thought would work didn’t.”

The late Anna Nicole Smith also made an appearance, and her constant drug-addled state provided Stewart with a bit of amusement. “I was used to viewers falling asleep during the show, but this was the first time we had a guest do it,” he said. “I’d ask a question and then she’d begin to try to answer. About halfway through it she asked, ‘What was the question?’ When we went to commercial—I had never seen this before—she had an Indy pit crew with her. All of a sudden eight guys come out and twist her head and slap her around, and there’s one lady in the front going, ‘Come on, you can do this.’ We came back and she was a little fresher.”

Finally, after years of working the wee hours at clubs all over the country in front of drunks and hostile people, he could relax… a little. Plus, he started to be recognized in public.

“It’s completely weird,” he said. “I was at this Denny’s in New Jersey at two thirty in the morning, and a bunch of kids home from college spotted me. They were like, ‘Wow! What are you doing here in Denny’s, man? You’re on MTV!’ They just were so exuberant, it really blew me away.”

After years of obscurity and still getting booed regularly, it was taking a little bit of time to adjust to television fame.

His increased visibility put him in demand in other entertainment venues. Now that he had a TV show of his own—albeit on a cable channel—other talk shows clamored to book him as did some of the comedy clubs that had blown him off when he was unknown. Hollywood also started to consider him for movies.

And he started to phase out a vision of his future being a miserable existence that he had carried around for years: “The prophecy I’d created for myself was one room without a bathroom, [where I was] a miserable old guy who will never love or be loved.”

With his fortunes rising, he was able to upgrade from his cramped studio apartment—it was so small that, in his words, he could “touch all four walls while perched on the toilet”—to a one-bedroom in Greenwich Village. He could have moved to a much larger apartment in a more expensive neighborhood, but the experience of his parents’ divorce and the financial challenges that followed were still fresh in his mind: the rug could be yanked out from under him at any moment. So he decided to play it safe.

“This is a business built on quicksand,” he said. “But I’m trying to get more perspective and allow myself to enjoy things. Occasionally, I’ll think, gee, this really is a lot of fun.

“It’s the little things in my life that have changed,” he said. “I don’t have to worry any more about taking a cab or buying a new CD.” Always an animal lover, he brought his two cats with him, one of which was blind. It took the cat a while to adjust to the new accommodations. “He kept walking into the walls, poor guy.”

He also thought his luck with women would improve once he got his own TV show—especially since a number of models, actresses, and even Playboy Playmates appeared on the show. “They come on, I feed them cheese, and they go, ‘Well, thanks a lot. I have to go now and have sex with a big construction worker–looking guy.’”

To his great dismay, the reverse actually happened, and he referred to his love life as stunted. “I’m finally in a position where women would find me more appealing, but I don’t really have that much time,” he lamented. “I’m basically really isolated, ’cause I work on the show all the time. And it’s sort of boring. A career is a lovely place to hide from your social life,” he said, adding that the top qualities he looked for in a woman were “compassion and a sense of joy.”

But even if he wanted to pursue women romantically, it was clear that they often regarded him in a different light. Once, after actress Tawny Kitaen appeared on the show, she revealed her true thoughts about Stewart. “You want to take Jon home with you, like a puppy,” she said.

He also discovered that hosting and planning four shows each week was worlds away from showing up at a nightclub, doing a twenty-minute routine, and then maybe having a beer with the other comics before heading back home or to a lonely motel room, with pros and cons all around.

“For me, coming from the comedy clubs, this is a very relaxed atmosphere,” he said. “Nobody’s drunk. It’s not one o’clock in the morning. I don’t have to shout. Everybody seems to be listening. It’s a really good environment.”

On the other hand, there was a great deal of stress involved. His anxiety levels went through the roof and he became sick so often that around the studio his nickname was Susceptible Boy. “My respect for the guys who [host talk shows] has risen dramatically since I’ve tried to do it,” he said. “There’s a lot to keep in mind while you’re out there.”

After all, Stewart was now directly responsible for a full staff. “I try to give as much preparation as I can,” he said, “but there’s a lot of other things that I have to worry about, not only the comedy but also the fact that we tape two shows in the course of one day, which sometimes puts us behind the eight ball.”

There was another issue that Jon never had to worry about onstage at the clubs: his appearance. He now had to select his wardrobe with an eye toward his audience and sit in a chair before each taping while a makeup artist did her stuff. “You don’t want to see him without makeup,” a Daily Show employee would say years later. “He’s not just sallow, he’s the color of a manhole cover.”

“They have to shave my neck… between tapings,” Stewart admitted. “Is that something I shouldn’t have shared?”

But overall, both host and guests didn’t get too worked up over the specifics. Given the informality of the set as well as the age of the demographic, a certain lack of style was the rule. “We could have the conductor of the Philharmonic on, and he’d be wearing overalls,” said Stewart. “I think everybody takes one look at me and says, ‘Okay, this guy looks like he just stepped out of a hamper. I can go on with grass stains.’”

The show hit big almost from the beginning, becoming the second most-watched show on MTV after Beavis and Butt-Head. The audience grew, and it also didn’t hurt that guests loved doing the show. “Letterman’s got a show he’s doing, whereas this is much more casual,” said Quentin Tarantino after appearing on both shows back-to-back. “This wasn’t like doing a talk show. It was like we were just bullshitting.”

“Usually, it’s not fun doing publicity for a movie or show, but I genuinely enjoyed doing his show,” said Daniel Baldwin, one of the Baldwin brothers, who was touting his role on Homicide: Life on the Street at the time. “He’s quirky, he’s nonchalant, and he lets you let your hair down. I would do his show again in a minute. It was a lot of fun. I even watch it now, and I never watch MTV.”

Despite the pressure of essentially driving blind during his debut, there was less to lose on MTV compared with one of the major networks. “It was much easier to debut on a cable talk show,” said Stewart. “There was no hype. It’s much better when viewers find you as opposed to being told to watch you.”

After six weeks of programs, he proved Stern wrong. MTV renewed the show and ordered another twenty-four shows. The New York Post called him one of the “hot new artists of the 90s.”

The boy from Jersey was finally on his way.

The first season of The Jon Stewart Show was so successful that Viacom—which owned MTV—decided to capitalize on Stewart’s popularity and move it to Paramount, a corporate division that handled syndicated TV shows, to fill an hour-long hole left in the wake of the cancellation of The Arsenio Hall Show. While MTV was indeed a national cable channel, the size of its audience paled next to the programs that Paramount syndicated on the local affiliates of the major networks nationwide. In other words, the size of Stewart’s potential audience was just about to get a lot bigger.

Stewart was thrilled. Not only would his show be syndicated across the country—not just aired on a niche cable channel—but it would be expanded from a half-hour to a full hour starting in September 1994.

He was also wary because the long show would require much more of his time and energy, and he had mixed feelings about that even after signing a five-year contract with Paramount. “I kind of liked my life [before],” he admitted. “I was enjoying myself on MTV. I was starting to branch out. I wouldn’t have taken the gig unless I thought I’d be OK if I lost it. But if you’re going to play it safe, don’t be in show business.”

His exhilaration didn’t take long to wear off. The ratings soon began to tank, largely in part because under Paramount, he had to kowtow to higher-ups in charge of massaging syndicated content to appeal to a broad range of affiliate stations in markets all over America. Previously, at MTV, catering to slackers who were too lazy to change the channel after Beavis and Butt-Head ended had been his primary worry.

At one point, Paramount suggested that he wear a tie on the set. His response: “I guess it would be nice, if someone was getting married on the show.

“It seems a conceit that if you have your own show, you wear a tie,” he said. “We do our show more from the hamper. Whatever we find that day floating on top that doesn’t seem dirty—boom. It’s right out there.”

Comedian Lizz Winstead, Stewart’s friend from the stand-up circuit, was asked to join the staff as talent coordinator. Her job was to find unknown but entertaining guests for the show, and she regularly combed through public-access cable TV shows for possibilities, but admitted it was a real challenge. “Some people are just crazy,” she said. “You can’t have them on because they’re certifiable. There’s this woman who thinks she’s Underdog’s girlfriend.”

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.

“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.