The marquee of the Chicago Theatre the last time, in 2006, Conan O'Brien played a show there.
Let it begin: The Chicago Theatre in 2006, the last time O'Brien appeared at the venue



Photo gallery: Conan O'Brien performs at Chicago Theatre

Conan O'Brien performs at Chicago Theatre

Dear Conan, I love you the most. Sincerely, your number one fan.

COMEDY There are two kinds of Conan O’Brien fans in the world: the kind that scream “Woo!” when they hear the words “masturbating bear,” and the kind that love the swirly-haired comedian for the deep intellect underlying his asinine antics.

Then there's me: I’m not your average Coco-lover. Is it weird to say that I love his soul? Yes. Yes, it is.

My creepiness aside, the ousted Tonight Show host brings his Legally Prohibited from Being Funny on Television Tour to town this week, putting on “a night of music, comedy, hugging, and the occasional awkward silence” at the Chicago Theatre tonight and tomorrow. Despite the steep prices—ranging from $39.50 to $79.50—tickets sold out almost immediately. But there are plenty for sale through sites like Craigslist and StubHub.

In May 2006, long before the NBC-Jay Leno fiasco that sent O’Brien packing for TBS (his new show launches in November), he taped four episodes of Late Night with Conan O’Brien at the Chicago Theatre. I attended a Friday show that included Wilco and then-Senator Barack Obama, and I can assure you, the one-hour taping was a rollicking good time. I can only imagine what a longer show without the FCC regulations might mean. His tour blog and Twitter updates suggest that Conan will be playing his guitar and singing quite a bit, as well as introducing new characters such as the “Self-Pleasuring Panda”—to replace their NBC-copyrighted counterparts.

Many familiar faces will join him at the show, including Andy Richter, the old band, and some of his former TV writers. Performances in other cities have included cameos by Eddie Vedder (Seattle) and Jim Carrey (Los Angeles). Not sure who’ll drop by on Wednesday and Thursday nights (guesses include Jeff Garlin and Bill Murray), but I’ll be happy just to gaze upon the pale, beady-eyed Coco as he croons to me in his bleating, nasal voice.

GO: May 19 and 20 at 7:30 p.m. $39.50 to $79.50. Chicago Theatre, 175 N. State, 312-462-6300.

  1. Conan’s 60 Minutes interview
    In the O’Brien’s first television interview since the NBC controversy, he talks about his post-Tonight Show depression, the comedy tour, and his new beard. BONUS: O’Brien’s wife, Liza, appears in the piece. I only grudgingly admit that she is sweet and pretty and perfect.
  2. Dinner with Jordan Schlansky
    O’Brien dines with a seemingly humorless metrosexual staffer and makes fun of him throughout the meal.
  3. Conan’s favorite clip
    When asked what video encapsulated him and his humor best, he named this Late Night clip in which he visits a park on Long Island where a group of history buffs re-enact old-time baseball games.
  4. Conan in Ireland
    Early in this talk-show-host career, a still-boyish-looking O'Brien visits County Kerry, Ireland, his ancestral homeland. He wears a newsboy cap, has a few beers, and interacts with the locals.
  5. @Google & YouTube Present: A Conversation with Conan O’Brien
    On the power of the Web: “The groundswell of Internet support from a lot of young people . . . completely took [NBC] by surprise. They don’t know what hit them. I think there are a lot of people in broadcast television that are very dismissive . . . about the Internet. And they’re also afraid of it. And they tend to deride what they don’t understand. . . . By the time we launched the tour, or announced the tour, I didn’t spend one penny on advertising. I sent out one tweet that directed people to a website where you could buy your ticket. That was it, and the show sold out in a couple of hours across the country. And that’s got a lot of people rethinking how things are marketed. There’s not one billboard, I didn’t have to go to one radio station. It was one tweet. I think people are starting to understand that the world has completely changed.”


Photograph: Esther Kang