Oprah: Would you rather be liked or be thought of as funny?
Jay: Probably liked. I think high self-esteem is overrated. A little low self-esteem is actually quite good. Some people with very high self-esteem tend to be criminals or egomaniacs, you know? I do understand that children should have good self-esteem, but there's nothing wrong with feeling like maybe you're not the greatest. Maybe you're not the best, so you should work a little harder. That was my mom's thing. Because I was dyslexic, she would say, "You're going to have to work a little harder than the other kids to get the same thing." My guidance counselor once jokingly told my mom, "You know, education's not for everyone. Have you thought of taking Jay out of school?" My mother goes, "No, why would he quit school?" She was furious at the guy!
Oprah: It's wonderful that your parents lived to see what you became.
Jay: Yes, but they never quite understood it. Back in 1986 when I was performing at Carnegie Hall, I got my parents two seats four rows back, dead center. So I'm onstage, and I see these college kids laughing during my performance, and my mom is going, "Shhh! Shhh!" I stop and go, "Ma, you don't shush people at a comedy show! They're supposed to laugh!" Remember that this was my mother's nightmare—to be singled out in a group of people. My mother was stunned. Then when I was on the cover of Time back in 1992, I called my mother and said, "Ma, go uptown and get a copy of Time." She said, "Now, which one is that?" I said, "It's Time magazine, Ma—one of the biggest." She said, "And you're on the cover?" I said, "Call Aunt Faye in New Jersey and everybody in New York, and tell them I'm on the cover." There was this long pause. Then she finally said, "I don't think you'd be on the cover there, Jay. They just put you on the cover here in Andover because they know you're from our area." That's what I mean when I say they never quite got it.
Oprah: Over the years, you've met almost every big star in the business. Have you seen stardom change people?
Jay: I've seen how brief a career in this business can be. There are people I'd never heard of when I started on the show who became stars three years later. We had worked like dogs to get them on the air, and the next time we'd hear, "Sorry, we're booked that week."
Oprah: Hasn't the ascent to stardom sped up?
Jay: Yes, and the heyday is only about eight years now. During that time, they're the handsomest or the prettiest.