Oprah: Were there any scandals that gave you your funniest material?
Jay: The Monica Lewinsky scandal was the golden age of comedy. A lot of people don't understand the Middle East or Iraq, but everybody knows a guy like Bill. I have a theory on why certain women like Clinton. He might try to have sex with you, but at least he'll also try to help you get your childcare bill through.
Oprah: So it's not his charisma?
Jay: It's that, too—but think of how many men really don't like women.
Oprah: You're in your 11th year of The Tonight Show. What's next for you?
Jay: More of the same. I'm pretty good at this type of piecemeal factory work. It's a young man's game, so I can't imagine another 20 years. By then I'll probably be doing the condos in Florida, entertaining the old people. But I don't really care what the venue is.
Oprah: Do you get anxious or feel threatened by new people coming on?
Jay: I feel threatened, and I welcome them. There's this big pie in show business, and you physically can't eat the whole pie. If you give everybody a slice of pie, you will still have more than enough. The real trick is not to try to get the whole pie, but to keep the biggest slice.
Oprah: Because you like winning, don't you?
Jay: I love winning! I'm a very competitive person. But I don't have to beat people into submission. I don't need to be the highest-paid guy on TV—that really doesn't matter to me. You can't spend all the money you make, anyway.
Oprah: I heard you've asked for less vacation.
Jay: I'm not a vacation guy. If I lose this job, I don't want it to be because I was lazy. I want it to be because I was incompetent or not very funny. When I was a kid, laziness was the worst crime. Once when I called home to talk with Ma, I found out that my dad had fallen off the roof and was in the hospital. So I hopped on a plane and flew home. When I got to the hospital at, like, 8:30 in the morning, I went to the front desk, chatted with the receptionist, and finally said, "Do you have a doctor's outfit?" So I put on the lab coat and hat and mask, and I walked into my dad's room and said, "What are you in here for?" He said, "You know, I've got this little thing...." I said, "We get a lot of guys like you in here." "What the hell does that mean?" he said. "I don't like your tone, fella." With my back to him, I said, "We get a lot of guys in here who've never worked a day in their lives, looking for a free meal and a bed." He jumped up and grabbed me by the throat and screamed, "You son of a bitch!" I said, "Pop, it's me!" It was hilarious! I'd said everything to push his buttons. Dad was just furious!
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