Oprah: I love it when you take the mike out onto the street. Don't people say the funniest things?

Jay: It's amazing what you get. It's not that you're so smart; it's just that most people are really kinda dumb. We can go to the most upscale areas, like Melrose, and ask, "Who was the first president?" The answer we get: "Lincoln." And here's my favorite question: "How was Mount Rushmore formed?" You know what the most common answer is? "Erosion."

Oprah: No!

Jay: Yes! Over thousands of years, the wind and the sky not only picked out four of our greatest presidents but knew to put the beard on Lincoln!

Oprah: When you're talking to people now, do you ever think back to your first time on Tonight?

Jay: Sure. Your first Tonight Show is a bit like your first girlfriend. You're not very good at it, it's over very quickly—but you want to do it again!

Oprah: Do you remember what you felt like standing behind the curtain, waiting to go out?

Jay: It was actually more nerve-racking afterward. I'd bought this enormous VCR, for like $2,000, just to tape it. So I remember being more nervous waiting to see the tape than I was during the real show.

Oprah: Does it get easier or harder?

Jay: Probably easier. Show business is like high school. It's hard to be the class clown when you're a freshman; you're just a smart-ass nobody knows. When you're a senior and you're the class clown, everyone says, "Oh, that's just Jay!" Even now when I embarrass a big star, it's like, "Oh, that's just Jay being stupid."

Oprah: Do you still feel compelled to work as hard as you did in the early days?

Jay: For so long, I worked for no money. I lived through "Boo, you stink, get outta here." I remember flying all the way to New York from Los Angeles, driving up to a theater, and finding it all boarded up. I was broke! They didn't even call me to say they were closed. Being a famous comedian gives you the first ten minutes free. New comics say things like, "It took me almost 20 minutes, but I got 'em." Once people know who you are, you have them from the start—but then you have to keep them.