Conan Calling
O'Brien Relives His Windy City Past
by Matt McGuire

Published May 8, 2006

Conan O'Brien remembers crying during the summer of 1988, the summer he spent living across the street from Wrigley Field.

"Crying the way someone would cry if their cat was crushed by a steamroller," he recalled during a recent phone call with metromix.

It was the summer the Cubs installed lights at Wrigley Field, though O'Brien wasn't crying because the city's loveable losers were breaking with Wrigley's daytime tradition and entering the twilight zone.

He wasn't crying because the Writer's Guild of America was in the middle of a 153-day strike, which meant O'Brien wasn't collecting a check from NBC, where he worked as a writer for "Saturday Night Live."

And most of all, he wasn't crying because the sketch-comedy show he co-wrote with fellow "SNL" writers Robert Smigel and Bob Odenkirk "Happy Happy Good Show," which played at Chicago's Victory Gardens Theatre was getting poor reviews. ("Most of the skits in this show fall flat, underdeveloped and incomplete," wrote a Tribune reviewer.)

O'Brien was crying because he couldn't take the heat. Literally.

"It was so hot that summer," O'Brien said, "I had a '72 Plymouth Valiant; that was my car, and it had air conditioning. There was no air conditioning in the apartment. [O'Brien's roommate and future 'Curb Your Enthusiasm' co-star] Jeff Garlin had air conditioning in his room. But my room had no windows. It was so hot in that room that I remember weeping."

"One night I walked down the stairs in my underwear gym shorts and no shirt, and climbed into my '72 Plymouth Valiant and turned on the car and just sat there with the engine running and the air conditioning on. I think it looked like I was trying to commit suicide."

"My roommates may have called the police. 'It looks like he's had it! He's running a hose into the car!'" O'Brien joked.

The writer's strike ended in August, and O'Brien left town shortly thereafter. Five years later, at the age of 30, O'Brien took over David Letterman's old NBC time slot.

Now, almost two decades after his last extended run in Chicago, O'Brien is returning as a king for a four-night run at the Chicago Theatre. He recently called us from his ninth-floor office at 30 Rockefeller Center and told us why.

Why Chicago?
Hawaii was too expensive. [Laughs] No, Chicago has been looming for us for a long time. We don't travel the show that much because it's incredibly expensive, which no one thinks about. They always think: "What do you mean? You jusy come to town and dance around like a chimp. You do that in New York. What could the difference be?"

We went and saw the Chicago Theatre a few months ago, and I think it's the nicest theater I've ever seen. I can't wait to ruin it with our nacho cheese bomb. I didn't tell you about that bit? A 30-kiloton nacho cheese bomb will be detonated the first night, shooting hot nacho cheese over the run entire city. I can't wait.

Several of your writers are from Chicago. Should we expect their best material for their triumphant return?
You know, I would have thought so, but no. [Laughs] They're all saying: "We're going to Potbelly's. Then we're going to the Twin Anchors." And I'm saying, but, c'mon, write something! Nah, really though, everyone's excited about it, but our Chicago guys are on their best behavior. So the minute they knew it was real, they've been coming up with funny ideas, all of which I've turned down. [Laughs]

Plan to hit the town after the shows?
I'm going to every strip club you've got. I'll be up there with the strippers. My goal while I'm in Chicago is do do the shows, make them as good as I can make them, but then I'm really going to make an effort to be out and around; I want crazy sightings of me in Chicago doing weird things.

I want people calling your paper saying, "I'm telling you, the guy was naked on a bicycle that looked like it was made of beef jerky, and it looked like he had a mining helmet on." And you'll be all, "No, no." Then a minute later you'll get another call: "I saw him. He was in the Loop. Hr was wearing a loincloth made of ham. And he was firing a pellet gun wildly into the crowd and shrieking."

Seems like meat and nudity play pretty heavily into your plans.
It always does. That probably should tell you something.