Lisa Rogak - Angry Optimist

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.

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.