Photo by Tyler Demogenes/Retna
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Jay Leno's Chicago
By Monique Burns, September-October 2003
After a lifetime on the road, every city is a blur for Jay Leno. But Chicago is his favorite blur of all
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When we decided to launch a new series asking well-traveled Americans to tell us about cities they love, Jay Leno was a natural choice: The Tonight Show host performs on the road 150 days a year. He's even headlining at AARP's big national event September 5-7 in Chicago, the very city he says is his favorite town to visit. Leno's Windy City recollections—quick-bite eateries, a club or two, a smattering of drive-by sights—reflect a performer constantly on the run. Not only did we get a glimpse of Chicago as we'd never seen it before, we got a surprisingly personal look at Leno's pedal-to-the-floor lifestyle.
Q.So, your favorite city is…
A. Well, I love Los Angeles. But, my favorite city to visit is Chicago. I'm in Chicago at least seven or eight times a year to perform. We've taken The Tonight Show there for weeks at a time. Chicago's a cool town. The buildings are not so tall that you get lost in those canyons. And, of course, to me, it's the best food town. It's a real good blue-collar food town.
Q. Well, we know that you've sent out for Fluky's hot dogs.
A. Yeah, those guys. They were pretty good. Then there's Demon Dogs—Demon Dogs under the El. That's a good one. And Billy Goat Tavern. Yeah, a verrry good burger. Then there's Mr. Beef, which is my favorite place to eat. Good Italian sausage. Al's Beef is pretty good. So's Portillo's.
Q. If you were going to take people out and really impress them, where would you dine?
A. Well, the kind of people I want to impress? I don't think I've ever been to a fancy restaurant in Chicago. That's why I like Chicago—you can eat standing up.
Q. When you take your wife out for a romantic dinner in Chicago, is it Billy Goat Tavern or Fluky's?
A. No, I like Papa Milano. One of those old Italian places, been around for years and years, looks like a little family restaurant. I order the same thing every time I go there. They have these giant meat raviolis. They look like pancakes. I have, like, five of them. So, I tell people, "I just had five raviolis—that's all I ate." But they're as big as your head! I'm not much for the fancy, you know, the fried quail on a bed of leeks or something. Just regular old cooking.
Q. Your dad was Italian, right?
A. My dad's Italian, my mother's from Scotland.
Q. Did your mom cook Italian cuisine?
A. Oh, yeah, my mom was a very good Italian cook.
Q. What about Scottish cuisine?
A. Scottish cuisine? I don't think there's any such thing. You know, Scotland is the heart-attack capital of the world. Because everything is deep fried. When you get a slice of pizza in Scotland, they put it in the deep fryer. Did you know that? And when you buy a Mars bar, what they do is take frozen Mars bars and then they dump them in hot oil. [In Scottish accent] "That's a treat. A delicious Mars bar." Like a Mars bar isn't bad enough for you—now it's fried. You see 28-year-old guys walking down the street in Glasgow—uh, uuuh!—they just fell over dead from a heart attack.
Q. Which Chicago landmarks do you really love?
A. There's still a lot of cool old buildings around Chicago with hidden treasures. Be they antiques, be they old car stuff, be they old bookstores. You know, the colder it is the better the bookstores, because people read in cold weather. It's a great city for knocking about in those types of situations. There's a lot of old machine shops hidden around in Chicago that I kind of like to poke around in.
Q. Is that just to get a feel for the place—or do you get parts for your cars?
A. Oh, a little bit of both. You talk to old guys, and they go, "Hey, lemme show you something."
Q. Have you been to The Museum of Broadcasting in Chicago?
A. No…that's my job. I don't go to work on my day off. Please.
Q. Stroll down State Street?
A. Like looking in store windows?
Q. Yeah.
A. No, 'cause, you know, I'm not interested in a Gucci hat.
Q. Well, then, other than looking around in antique places…
A. Junk shops.
Q. Junk shops. Other than that, do you like to go shopping?
A. No. Since I started The Tonight Show, I can honestly say I have never gone shopping. I give the wardrobe guy here money to go down to Banana Republic and buy me 15 pairs of jeans and 30 shirts. That's my personal shopping for the year. I don't own a suit. My suits all belong to NBC. So, I come in here, and I go, "What am I wearing today?" "Here you go." God, I haven't been in a store in, geez, it's been 10, 11 years.
Q. Do you ever get a chance to go out to Wrigley Field?
A. You're asking if I've seen a sporting event?
Q. Uh-huh.
A. No.
Q. How about golf? Do you ever play any golf?
A. Oh… golf… Is there enough money in the world to get me to play golf? I mean, is that fun...golf??? Hit the ball and just walk over here and hit the ball again. No, I don't get that one. Oh, I understand it's a wonderful game and people are fascinated by it, but gee…
Q. Well, what do you do to relax?
A. You know, I don't really relax. I do The Tonight Show every day, plus I do 150 personal appearances a year. I mean, I'm not much of a relaxed guy. I've never taken a vacation or anything like that: "Oh, let's just go sit in a foreign city for two days…" That would drive me batty. Truth is, I don't really travel for pleasure. I land at 3:30, look around for a little bit, grab something to eat, gig's at 8, come home at midnight. I'm not much of a sleeper. If I sleep more than four hours, I feel horribly guilty. So, you know, going out and doing sports and vacationing, those kinds of things don't really interest me very much.
Q. If I were writing Jay's travel book…
A. There'd be no such thing. My wife loves to travel. I send her and her mom anywhere in the world. Like Venice. But for me it's like a bad day at Disneyland, you know?
Q. Any favorite hotels in Chicago?
A. [Laughs] No, not really. I mean, you know, my life is, you go in the back door. They take you up the freight elevator. "Here's your key." And then you leave.
Q. Okay, well…
A. [Helpfully] Listen, Chicago has some great blues clubs. I can pretend to like blues.
Q. Do you like blues?
A. It's all right.
Q. What's your favorite blues club there?
A. Oh! Oh! You know, we went someplace and we had a good time. Because I used to tour with Muddy Waters and a bunch of those old blues guys. I think Muddy had a club there in town.
Q. What do you think of the Water Tower, that little castle?
A. Yeah, yeah, I think I was in that.
Q. Was it an architectural highlight?
A. Yeah, yeah, put that down. That's a great idea. Architectural highlight. Yeah, that'll work.
Q. If you say so…
A. Put me down for two of those.
Q. [Awkward silence]
A. So, this story's gonna be pretty much a paragraph, isn't it?
Monique Burns is a former senior editor at Travel & Leisure magazine.
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