Oprah: In the early nineties, I realized I'd been imitating others because I thought I needed to. I now know that the show has to come out of me.
Jon: Otherwise, how could you sustain it? When I first got on Letterman five years into my career, I thought, This is it—the end of my rainbow. He was the Carson of my generation. On the show, I did as well as I could. When I woke up the next morning, I wasn't any taller, I had a head cold, my apartment still had roaches. That's when I realized, This isn't about moments; this isn't about getting to the next place. It's just about being good. Then I got a show on MTV.
Oprah: What was that called?
Jon: Such an original title—The Jon Stewart Show. That did well enough for me to get Arsenio Hall's job after he quit. I was scared shitless. About four months into it, I thought, "Wow, this unbelievable opportunity will be taken away from me, and when someone asks, 'Did you even enjoy it?' I'm going to say no." I remember the night when I just exhaled.
Oprah: That happened to me when I was onstage dancing with Tina Turner. The song was only three minutes and 27 seconds long, and I was so nervous. Suddenly, a voice in my head said, "You've already wasted a minute. You'd better enjoy this!"
Jon: If this were Hollywood, the story would be that I relaxed and then built an empire, and 30 years later, that show is still going strong. Well, I relaxed, and five minutes later they locked my door and didn't let me back in the building. I got fired. But I had a hell of a time. I woke up the next day and it was the opposite of the Letterman experience. I thought, "Okay, my apartment is no worse and I can still write jokes." In that moment, I realized I had suddenly become competent. I had lived through the loss I feared.
Oprah: That's a pivotal adult moment.
Jon: A month later I met Tracey.
Oprah: How did you meet?
Jon: On the only blind date either of us had ever been on, at a Mexican restaurant.
Tracey: The date wasn't blind for me.
Jon: Tracey had seen me on TV.
Tracey: It's a fairy tale from my end. I had just gotten out of a seven-year relationship. I was depressed, and my friends were trying to set me up all the time. After a bad date, they'd ask, "What are you looking for?" I had discovered The Jon Stewart Show, so I said, "Someone funny and sweet, like Jon Stewart." My roommate was working on a movie set, and Jon knew someone who worked on that set. So Jon stopped by to say hello. They were all sitting around talking about how they weren't having much success with dating. My friend said, "I have a roommate who thinks you're cute. She saw you on TV." And, of course, Jon immediately thought...
Tracey: Right. Because my roommate was always setting me up with actors, I'd said, "No more performers." So she told Jon, "Actually, it goes against you that you have a television show." Then she told him more about me. Jon said later that he'd never heard someone talk in such a loving way about a friend.
We Hear You!