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

Cornell grad Keith Olbermann started his broadcasting career as a sportscaster, working in Boston and LA before moving east in 1992 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 longstanding 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. Naturally, 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. However, Olbermann got into some hot water himself in 2010 when he donated large sums to Democratic candidates, breaking company policy. He was quickly suspended and then left MSNBC in 2011 for the much smaller Current TV, where Countdown continues with the same basic format.

Sadly, the love affair was not to be; Al Gore gave Olbermann the boot on March 30, 2012, less than a year after he began his stint Current TV. He was replaced replaced by former New York Governor and fallen sex-angel, Eliot Spitzer.
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