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Jay Leno needs no introduction. After years of working his way up in the standup scene, the comedian became a household name when he took the reins of NBC’s The Tonight Show in 1992. This March marked the beginning of his 18th season as host of The Tonight Show with Jay Leno.

Leno recently made headlines when he reclaimed the late night spotlight from Conan O’Brien and returned to host The Tonight Show after a brief six month move to primetime. Despite taking some flack in the media, Leno is regarded as one of the nicest and hardest workers in show business.

Usually the one asking the questions, Leno took some time to answer our questions leading up to his visit to Chicago for JUF’s Vanguard Dinner this Sunday, Oct. 24.

The iconic funnyman shares an odd experience in the Catskills, tells us his take on Jewish humor, and explains why he loves working with his famous collection of cars and motorcycles.

Oy!Chicago: We’re going to see you here October for a Jewish Federation dinner. Do you tailor your stand up routine based on your audience?
Jay Leno: I remember years ago, I had an agent in New York City and he says, ‘oh you’re going up to a resort in the Catskills, I booked you up there.’ He didn’t tell me it was a Chasidic resort. I pull up and the marquee says ‘Jay Leno, Jewish storyteller.’ This agent had booked me as a Jewish storyteller. And I go there and everybody’s Chasidic and they’re all speaking Yiddish and I walked out on stage and first, they were surprised that I’m speaking English, and I was like ‘um guys, I’m not…I’m Italian and the agent uh kind of…, and they were very nice they were really nice people and I was a kid—I was like 20 years old. It’s just very funny. It’s just one of those sort of odd things.

It just seems like an important event to do. I like people who are proud of what they are, whatever group it might be. I like people who take care of their own and are proud of what they do and everyone should be proud of who and what they are. Organizations that do that are good organizations, whether it’s Jewish or any other.

You once told a colleague that there's no such thing as a stereotypical Jewish mother because all mothers are Jewish mothers. Is there such a thing as Jewish humor?
Any people that have gone through hardship—the best way to deal with it is through humor, so I think there obviously is sort of a Jewish sense of humor. I’m not quite sure how you would define it. Jewish people put such a heavy emphasis on family and education, and that type of thing, and there are stories in the Jewish culture about how important that is, and those tend to be funny stories, in terms of being protective or whatever it might be. To me, Jewish mom is just another word for good mom. So if you call someone a Jewish mother, you’re giving them a compliment. But yeah, of course there is Jewish humor. It’s one of those things, it’s cultural, it comes from where you grew up; it comes from constantly living in one world and having to deal with another.

Who is your favorite Jewish comedian of all time?
Well when I was a kid, my mother loved Myron Cohen. My mother had a very hard life—she came to this country by herself when she was 11. My mom’s natural inclination was not necessarily to smile. She wasn’t a depressed person, but whenever I’d look at my mom as a kid, my inclination was always to do something to try to make her laugh. Whenever Myron Cohen was on TV, my mother used to laugh out loud and I used to think, ‘I wanna be like that Jewish guy.’

I think my mother’s favorite Myron Cohen story was the one about a Jewish grandmother who takes a kid to the beach. She’s been trusted with watching the child and she puts the child down on the sand. She takes a couple of steps [back] and a big wave comes in and washes the baby into the ocean. Right away the Jewish grandmother [begins to pray]: ‘Oh my God. I was left with this child, my only grandchild, please God I’ll do anything, I’ll do anything, I’ll go to temple,’ and on and on… Finally a big wave comes back and drops the kid on the beach totally unharmed and she walks over to the kid and looks up at the sky and says, ‘he had a hat.’

Jackie Mason, Alan King… The best comedians are always the Jewish comedians…

In your autobiography you say you are incapable of taking a vacation. Is that why you continue performing standup on your time off from The Tonight Show?
If you’re doing what you like, it’s not really work. I like to tell jokes; it’s fun. The stage is not a normal place to be, so the more you’re on stage the more natural it becomes to you and that’s really the key. If you’re a runner you can’t just do marathons, you’ve gotta run every day and it’s the same thing with comedy. You’ve gotta perform at least two or three times a week to keep yourself sharp and keep on the ball.

What is your favorite Tonight Show segment?
To me I like the Jaywalking and the Headlines.

Who is the coolest person you’ve interviewed to date?
Coolest interview would have to be President Obama.

Do you have a favorite car or motorcycle in your collection?
If I had a favorite I wouldn’t have all those cars! When you work with your hands you get a sense of perspective. Comedy is very subjective; some people thinks it’s funny and some people think it’s not, and neither one of them is correct. It’s what works for you. But when you have something that is broken and you repair it, and it actually runs, no one can say you didn’t fix it. Plus, when you work with your hands and you put a transmission in or you put in an engine, and you realize the average person made $100 bucks for that, you realize how fortunate you are to be in show business.