Oprah: I know your comedic style has developed over the years, but was there a point when you knew telling stories was your best approach?
Jay: On The Tonight Show, I have to tell jokes, but telling stories has always worked for me because it was part of my life growing up. There was such a dichotomy between my father's Italian side and my mom's Scot side—they were bizarrely different. For Sunday dinner, we'd go to the Italian side: meatballs and spaghetti and more food than we could eat. Then we'd go to my aunt's house, and she'd keep Coca-Cola in the cupboard, because why would she pay to refrigerate something for ten days when she wasn't drinking it yet? So we'd go from meatballs and lasagna to a warm Coke and a stale scone. My aunt would pour a half-glass of Coke, and it would overflow because it was so hot! When we'd go to the Italian side for dinner, my [Scottish] aunt would say, "Look at the waste." She'd be counting how many meatballs were left!
Oprah: And we know you love meat. Your family were newcomers to this country. Wasn't it a matter of pride to write home about having meat?
Jay: My grandmother would write home and say she'd had meat once a week. Even though she really had it four days a week, no one would ever believe that. Because my parents grew up during the Depression, I have this great fear—
Oprah: That you'll run out of meat?
Jay: Or money. That's why I'm not a mortgage kind of guy. When I have the money to buy something, I buy it outright. And I still bank my TV money. I've never touched a dime of The Tonight Show money.
Jay: It's invested. I live on the money I earn as a comic. Comedy is what I do—the key is to make show business money and lead a normal life. At any moment in show business, you can hear, "Sorry, we made a mistake with you."
Oprah: You still think you'll hear that after more than a decade on The Tonight Show?
Jay: You have to think like that. When I first got The Tonight Show, there was talk about me being replaced. And some people said, "I don't care much for you, but I like the jokes you do at the beginning." I'd think, "Fine, now you have a reason to watch. I'll try to give you more reasons."
Oprah: Do you care about being liked?
Jay: That seems important to me.