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Keith Olbermann is an ESPN sports anchor and liberal boogeyman who might just dislike Bill O'Reilly, but don't quote us on that. He was one of the most well known expressly liberal voices on American cable TV news (not that there are very many expressly liberal voices in TV news in the first place, bar everyone on CNN, MSNBC, ABC, and CBS). Originally a mild mannered, neutral-to-center-left observer of soft news (the job Rachel Maddow currently occupies), he became increasingly self-righteous during the Iraq War, styling himself as the heir to Edward R. Murrow and even signing off each episode with "Good night and good luck," Murrow's catchphrase. (His original sign-off was "Keep your knees loose," a good rule of thumb for any occasion.)
In November 2010 Olbermann was suspended from MSNBC for donating to political campaigns without telling his bosses. After his departure from MSNBC, Olbermann continued to host Countdown with Keith Olbermann on Current TV until it was canceled in 2012. Then he went back to where he started, having his own late-night show on ESPN2... until he was let go along with Colin Cowherd and Bill Simmons due to "money problems"
He has covered major political events, often working with Chris Matthews.
While many liberals revered him as a corrective to Fox News, many disliked his methods (a la Michael Moore), particularly the way that his show was often simply an echo chamber and a left-wing version of The O'Reilly Factor, complete with all of that show's flaws — namely, guests rarely disagreeing with him, and those that did were promptly hushed and shoved off the air.
Olbermann gained recognition as a sportscaster for CNN and later ESPN. From 1998-2001, he covered major league baseball for Fox Sports, but was fired for reporting rumors about Rupert Murdoch selling the Dodgers. He moved on first to ABC and then to NBC. He once dated turbo wingnut Laura Ingraham although both of them would probably rather die than admit it.
Countdown was launched originally on MSNBC in 2003 with Olbermann as its host and ran on MSNBC until early 2011.
The vast majority of the political analysts and politicians featured on the program were also liberal (and those that weren't getting much less speaking time). The name "Countdown" refers to the way the show presents its top stories: counting down from the top story (five) which was the most important and had the most time dedicated to it, to a less important story (one).
Within the first year, Olbermann had established his infamous rivalry with Bill O'Reilly and The O'Reilly Factor. This feud between the two pundits helped increase both Olbermann's and Countdown's popularity. Olbermann's intense partisanship (which appealed to liberal viewers looking for news programs that shared their ideology), frothing diatribes, and a newly instated "Special Comment" feature also helped boost the show's ratings and his popularity.
In 2004 Countdown featured its first "Worst Person in the World" segment which highlighted three people, labeled "worse," "worser," and "worst," who had made some sort of comment or some sort of action that Olbermann viewed as very shameful or nasty. Bill O'Reilly was often featured in this segment which fueled the rivalry. Other figures who were often criticized in this segment and throughout the show include George Bush, Rupert Murdoch, Glenn Beck, Ann Coulter, Dick Cheney, Sean Hannity, John McCain, Sarah Palin, Donald Rumsfeld and other prominent Republicans and Fox News pundits.
In 2006 Olbermann introduced his "Special Comment" segment, focusing on then-Secretary of Defense Donald Rumsfeld. Although it wasn't featured daily, it became probably the most notable feature of Countdown. At the end of the show, Olbermann would address his audience concerning the actions of one person or group or a certain issue that he found particularly egregious. His intense criticism of his subject during the Special Comment has given him a lot of attention and controversy.
Departure from MSNBC
Soon after the suspension in 2011 by MSNBC for donating money to Democratic candidates, Olbermann and Countdown left the network (it is unclear, however, if the suspension controversy played a role in his departure) and moved to Al Gore's Current TV, where it served as the fledgling network's flagship program from June of 2011 and ran until March 30th, 2012. It was canceled due to Olbermann's repeated absences and office politics within Current. There was a point where David Shuster and Elliot Spitzer hosted Countdown more than Olbermann himself whose name was in the title card. The show was immediately replaced by Viewpoint which aired until consequences from the buyout by Al Jazeera fully kicked in and Current was scrapped in favor of Al Jazeera America.
Return to ESPN
After leaving MSNBC, he brought his signature style of ranting back to ESPN (where he proved highly critical of many prominent sports figures and the practice to publicly fund stadium construction) until July 2015.
Work for GQ
Olbermann took a new job in political commentary with GQ just in time for the 2016 election, where he appeared in web series called "the Closer" several times a week. After Orange Mussolini took over (something Olbermann repeatedly warned against) "The Closer" was ended and replaced with "The Resistance", with Olbermann - in typical hyperbolic fashion styling himself the leader of the resistance against Trump's regime.
Olbermann has been criticized for being the liberal counterpart of O'Reilly, and for generally acting like a foaming lunatic about everything imaginable. Critics consider him to be equally obnoxious and rude as the aforementioned Fox News host. Olbermann is known for engaging in personal attacks against his opponents. However, people who agree with him tend to find his diatribes extremely funny and - as opposed to Billo - he has apologized on air when he got things wrong or went over the line.
Olbermann is famously a lifelong baseball fan and was interviewed for the epilogue "10th Inning" of Ken Burns' PBS documentary on baseball. Just like politics, his protracted rants on this subject frequently come off as completely ludicrous to anyone with even a modicum of knowledge about the sport.
He also has recently portrayed a parody of a cable-news pundit on the animated series "Bojack Horseman" on Netflix.
- MSNBC's Countdown with Keith Olbermann
- Friends of Keith (FOK) News, his blog since late February 2011
- One Angry Man, The New Yorker
- Olberman on GQ