In character, Colbert created apparent dyspepsia among some portion of his Washington A-list political and media audience. The dinner draws more than 2,500 and is a very curious function, underscoring the depressingly incestuous relations between the political establishment and a few too many journalists, some of whom so deeply crave the acceptance of whoever's in power. It's morphed from a rather staid gathering into a smoochy celebrity gang bang and sucking up to politicians, with media organizations inviting both people they cover and famous actors and other pop culture stars as guests, and doing so with competitive fervor in their search to look hip.

(Full Disclosure: As Chicago Tribune Washington bureau chief, I finally succumbed to virtual Abu Ghraib-like pressure from colleagues and scraped our traditional resistance to this silliness, inviting "Law And Order" stars Jill Hennessy and S. Epatha Merkerson in consecutive years. And I had a fine time. But I did exhibit limits, and Patton-like decisiveness, in telling one famous actor, who can afford to buy much of the construction debt in Dubai, to take a hike after he insisted that I also fly his girlfriend from Seattle and put him up under a pseudonym at the Willard Hotel).

That year brought President George W. Bush to the dais, with his discomfort obvious as Colbert's right-wing character theatrically tried to offer support. Colbert's show host said the two of them weren't "brainiacs on the nerd patrol." He talked about some Bush White House staff changes as "rearranging the deck chairs on the Titanic." He cited Bush's declining poll numbers and said, "We know that polls are just a collection of statistics that reflect what people are thinking 'in reality.'"

The Internet was abuzz for days, with some mainstream media outlets then criticized for catching up with the story very late. In Chicago three and a half years later, Colbert left no doubt that his recollection of the night is sharp, starting with correcting a questioner about the dinner's date.

"April 29, 2006," he said at the Second City reunion, eliciting laughs. "I still wake up with a pain in my shoulder."

Colbert said he was genuinely surprised that he'd been invited to the affair and, with his colleagues, "worked very hard on it and the actual performance." It was an honor, a rare opportunity. "The actual performance was enjoyable for me. I really liked the jokes and was eager to do it."

Tom Purcell, a Second City alum and the television show's co-executive producer, explained the tactical rationale: Bush, he said, was the typical "Big Man" one might find in innumerable institutional settings. "We thought it was the Big Man. He hires somebody to make fun of him, and he chuckles. You see it at office Christmas parties. You say the boss is so cheap that....and he laughs and everybody laughs. That's what we thought we were doing. They wouldn't have brought us in if they didn't know what jokes we did."