The New Yorker has a rollicking good overview of Keith Olbermann, from 2008:
http://www.newyorker.com/reporting/2008/06/23/080623fa_fact_boyer?currentPage=allCBS considered him to replace Dan Rather.
He has restless leg syndrome. He also cannot drive since his equilibrium was damaged after bumping his head in a subway door.
Olbermann on Tweety: "Like an out-of-control sprinkler system."
...Olbermann’s style stood out from the start. He gently mocked the conventions of sportscasting (in his deep broadcaster’s timbre) even while observing them. At UPI, he became famous for drolly tallying the number of times athletes said “Y’know” during interviews. He also had a sometimes overbearing self-certainty. When he was twenty-three, he told Bill MacPhail, the former CBS Sports executive who had overseen the introduction of instant replay, that MacPhail didn’t know anything about television sports. In an argument with one of his supervisors at UPI, he so forcefully advocated his position (“God damn it, this is the minor leagues here,” he said, “and it’s things like this that are keeping us the minor leagues’’) that he was fired that afternoon. (The Wire Service Guild stepped in and saved his job.) His three-year career at CNN was, he says, “a continuing pitched battle.” He moved to a television station in Boston, and lasted a few months. At the age of twenty-five, he moved back home, a flameout, with few prospects. His agent sent his highlight tapes to stations around the country, but most station managers didn’t quite know what to make of him. “The standard response,” he says, “was ‘I like him, but is Baltimore ready for him?’ ”
Jeff Wald, who was then the news director of KTLA Channel 5, in Los Angeles, had heard the stories, but he saw Olbermann’s tapes, and was curious. “I just said, ‘He’s the guy,’ ” Wald recalls. “Regardless of the baggage he may or may not have, I want to meet this guy and see if he’s the real deal. And he was.”
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