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How did a nice Italian boy like you end up getting into comedy?
When you grow up in Massachusetts, you aren’t really encouraged to go into show business. I always remember my neighbor lady saying, “You can’t be a comedian unless your father was a comedian — that’s how it is in Hollywood.” But my dad was a salesman, and once a month, he would put on a show and play records and have contests to motivate the salesmen. He enjoyed writing the jokes and telling stories, and I thought it might be fun to be a salesman and put on these little shows too. And I was quite lucky because I had an English teacher, Mrs. Hawkes, who stopped me in the hall one day and said, “I always see you telling these jokes. Why don’t you take my creative writing class? You can write your jokes and stories, and I will give you English credit for it.” It was actually the first time I enjoyed doing homework. When I read my jokes in front of the class, I was curious to see where the laughs were. I was always quite grateful to Mrs. Hawkes for seeing something more in a kid who was kind of rambunctious — and for encouraging me and guiding me to find something I really enjoyed doing.

The first time I told a joke, I was in fourth grade with my friend Ben. We had decided to be a comedy team. We only had one joke, and it took quite a bit of effort. I wrapped him in bandages from head to toe like a mummy and took him into class. He had a sign in front of him that said 3000 BC, and someone said, “What does that mean?” And I said, “Oh, that’s the license plate of the truck that hit him.” That was the only joke we had.

As a kid, I was always really aware of the reactions of adults to anything funny I said. I had a lot of Italian aunts, and they were always a good audience. I remember when I was only four years old, I said, “Why do women have humps like camels?” And my aunts all started shrieking with laughter, and I liked the reaction. I thought, I’ll have to remember to say that again. Another teacher of mine, Mrs. Allen, whom I am still in touch with today, was talking about Robin Hood in class, and she said Friar Tuck was boiled in oil. I said, “Was that because he’s a friar?” And she said, “Oh, Jay, stop it!” But I saw her laughing and knew that she thought it was funny. Then one day, I went to the movies by myself and saw Elvis singing — and all the girls and women screaming — and I thought, Forget about being a salesman. I’ve got to figure out how to do this show-business thing. This is the way to go!

Who are your favorite guests?
I like the guests who are real. Actors are fun as guests, but ultimately, they are playing characters. Real people who have done something extraordinary are the most fun to interview. American heroes are always great guests. One of my favorite guests of all time — and I’ve told this story before — was John Glenn. When I was in fifth grade, I had to write a paper about John Glenn because he had first circled the earth in 1962. I wrote that paper, and I think I only got a C on it. So when John Glenn went back into space in the ’90s at the phenomenal age of 77, I thought it would be a great opportunity to improve my grade. This is one of the advantages of having come from a small town. I called my fifth-grade teacher and asked if I interviewed John Glenn, could I get some extra credit 40 years later and improve my grade? I told John Glenn, and he liked the idea — and after the interview, my teacher raised my grade to an A, which thrilled my mom.