"Mr. Bush, the question is no longer, 'What are you thinking,' but rather, 'Are you thinking at all?'" he said in a now famous commentary.
That diatribe against the president and the war in Iraq spiked the ratings of Olbermann's show, "Countdown." Its viewership is up 85 percent in the last year.
"Funny things happen sometimes," he told 48 Hours correspondent Susan Spencer. "The wages of sin are sometimes not what you expect."
In his case, the "wage of sin" for being outspoken, opinionated and irreverent, is "Countdown," a one-hour rollercoaster ride of a newscast every weeknight on MSNBC. It's not just politics; Olbermann counts down the day's top stories, from soup to nuts — the whole wacky world as he sees it.
His background hardly explains the wackiness. He grew up in the New York City suburbs. His dad was an architect and his mom was a schoolteacher, but he did pick up their take on politics.
"There wasn't any particular political conversation going on. There was a kind of broad-based assumption that they were all idiots," Olbermann said.
He picked up his mother's take on his other passion, baseball.
"My father detested sports — had no interest in it whatsoever," he said. "I would go to Yankee games with my mother, and we were the baseball fans."
But it was his father who accidentally steered him down his current path. His father told him he could listen to baseball games late at night on the radio, only if the lights are off and the room was dark.
"That's gonna inspire any kid's imagination," Olbermann said. "And so, this took me to far off, Kansas City, in my mind. Exotic places like Washington, D.C. And I became a fan of the announcers, as much as of the players."
In 1992, after stints in Los Angeles and Boston, Olbermann made it to sports nirvana: ESPN and "SportsCenter." However, it wasn't providing everything he really wanted out of his career.
"When you're actually on the air, and doing what you have sort of trained your entire career to do, obviously that part is exhilarating, but there were some drawbacks to it," he said. "One of them being, 'When are we going to talk about something besides sports?'"
After leaving ESPN in 1997 he bounced between news and sports until 9/11. Olbermann, who lives in Manhattan, was sleeping when it happened and didn't learn about it until he heard a voicemail from a friend asking if he was alright. A friend who ran a radio station in Los Angeles asked Olbermann to go on the air.
"So, I did. And, for 40 days, I was their street reporter," he said. "Best kind of therapy that you could get, as you know."
That therapy won him awards and swung the career pendulum back to news and eventually to "Countdown."
"You need to make a newscast that looks like life," he said. "Very serious, very angry, very stupid, very silly, very snarky — very much about pop culture."