Who

Olbermann is a wisecracking sportscaster-turned-wisecracking political pundit and left-leaning counterweight to his Fox News opponent Bill O'Reilly.

Backstory

Cornell grad Keith Olbermann started his broadcasting career as a sportscaster, working for CNN and WCVB in Boston before moving to Los Angeles, where he spent time at local affiliates KTLA and KCBS. In 1992, he moved east to join ESPN and spent five years hosting the enormously popular SportsCenter with Dan Patrick. Ready for something new, in the late 1990s Olbermann joined MSNBC to host The Big Show, only to defect to his future punching bag, the Fox empire, soon after, hosting The Keith Olbermann Evening News on Fox Sports Net. In 2001, he left Fox to work in radio for a spell, before settling into his current position as the host of Countdown on MSNBC in 2003. He started the week the U.S. invaded Iraq.

What started out as a conventionally plain-vanilla evening cable broadcast evolved into something with bite, as Olbermann injected more and more anti-Bush jabs into his speedily-delivered countdowns of the five biggest stories of the day. These days Olbermann is MSNBC's biggest success story, not that he has much competition on the third-place news network. His broadcasts average a million viewers, his show performs especially well with the 25-to-54 age demo, and he's become the face of the channel's effort to position itself as a less geriatric, left-skewing alternative to the Fox News Channel and a livelier alternative to CNN. NBC News has been busy trying to fortify the Olbermann brand as of late—the network has debuted several Olbermann specials on NBC proper and has been aggressively promoting Countdown in ad campaigns.

Grudge

Olbermann has an ongoing battle with Fox News's Bill O'Reilly, whose show shares the same 8pm time slot as Countdown. Among other jabs, Olbermann frequently includes O'Reilly (or "Bill-o") in his nightly segment entitled "The Worst Person in The World" (often alongside Rupert Murdoch), and takes enormous delight in squeezing in frequent mentions of the Fox host's 2004 sexual harassment brouhaha. For his part, O'Reilly has tried on numerous occasions to get Olbermann fired, and once threatened to send Fox security guards to the home of a caller who had the audacity to mention Olbermann's name on the air. The O'Reilly-Olbermann conflict isn't just entertaining. It's good for ratings, too. Since taking on his much bigger rival, Olbermann has seen his viewership edge upwards and he now presides over the most popular show on the network.

Keeping score

Olbermann raised some eyebrows in late 2006 when he asked NBC to quadruple his salary to just over $4 million per year. In February 2007, NBC announced that it had re-signed him to a new four-year deal but didn't disclose the terms.

Drama

Olbermann learned about the danger of email the hard way. Once known for replying to the messages sent by fans, he got into hot water when several of the emails were posted publicly. "Rita's nice, but dumber than a suitcase of rocks," he wrote of fellow MSNBC reporter Rita Cosby. He also had a one-night stand with a fan, a thirtysomething Cuban woman with whom he'd corresponded for 18 months. Much to his embarrassment, she subsequently blogged about how unsatisfied she was with the encounter, and either was "given" or "stole" one of Keith's ties, depending on which party you ask.

Personal

Olbermann has never been married. In 2007, he moved in with his girlfriend, aspiring television journalist Katy Tur, who is 25 years his junior. The couple live in a 40th floor condo in the Trump Palace on East 69th Street; Olbermann paid $4.2 million for the pad in April 2007. One of his neighbors is Carrie Chiang.