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"I'm difficult for management. That's why I have the reputation because nobody challenges management."

Keith Theodore Olbermann (born January 27, 1959) is an American commentator, originally known for sports commentary, but in the mid-2000s became equally well-known for his political commentary.

A graduate of Cornell in 1979, he started in sports broadcasting at the wire service UPI in 1981 before moving on to the sports division of the newly-founded CNN, and then local sports broadcasting in Boston and then Los Angeles. In 1992, he joined ESPN's Sports Center as co-anchor with Dan Patrick. His tenure is considered to be the point where Sports Center really took off, with his on-air persona inspiring one of the characters on the short-lived Aaron Sorkin drama Sports Night. After disputes with management, he left in 1997, seemingly burning his bridges in the process, though he would remain friends with Patrick.

It was at this point Keith would make his first foray into non-sports news, as host of a primetime news show on MSNBC, The Big Show with Keith Olbermann, a reference to a book he had co-authored with his former Sports Center co-host Dan Patrick. The show began to focus more and more on the 1998 Monica Lewinsky scandalnote , causing Keith to quit and go back into sports, this time at Fox Sports, who fired him in 2001. He would hold a series of journalistic odd jobs for a few years, writing a column for Salon, freelancing for CNN, and filling in for radio broadcaster Paul Harvey.

In 2003 he went into political journalism at MSNBC again, this time with much more success than the last: Countdown: Iraq, the show that would shortly evolve into Countdown With Keith Olbermann. It found its voice as a left-wing foil to shows such as those found on Fox News Channel. Among the recurring segments were "The Worst Person in the World", in which bronze, silver, and gold medals were awarded to politicians and pundits that had performed particularly repellent gaffes, scandals, or general fuck-ups that week - though a part of the people on the list were "awarded" the honor as a joke and Keith even put himself on the list from time to time. Not all who were put on the list found the "joke" particularly funny, though. Bill O'Reilly was an early and frequent recipient of this award, and this led to a long and recurring feud between the two.

Just before the 2010 U.S. elections, Olbermann was suspended for making donations to three candidates for office without seeking MSNBC approval. A petition was circulated to get him reinstated, and while it looked like all would be back to normal, in January of 2011 he announced he was quitting MSNBC. Shortly thereafter a new show, also named Countdown With Keith Olbermann, would feature on Al Gore's CurrentTV network, following the same formula. CurrentTV fired him after less than a year, and itself folded in 2013. His departure from Current was almost as tumultuous as his departure from ESPN had been and some issues ended up in court.

On July 17, 2013, Olbermann re-joined ESPN, prompting reactions of Cue the Flying Pigs considering how acrimonious their earlier split had been, and a sign of just how seriously ESPN took Fox's heavily-hyped sports network. They launched a new late-night sports-based show titled Olbermann on August 26 on ESPN2, a hybrid of his sports (highlights, or as they were called "Keithlights") and political (Worst Persons, interviews with people in sports and sports-fan friends of Keith's, commentary that aired at the start of the show this time, and for the first year, Time Marches On, all sports-centric) pasts. As the show continued, rumors began to circulate that higher-ups at ESPN were becoming concerned with Olbermann's continued taking of Countdown-style shots of people and sports organizations when on-air, particularly at the NFL its chairman Roger Godell, over the league's handling of on-field head injuries and domestic violence cases involving players. (ESPN has a deal with the NFL that runs through 2019 worth over $15 billion.) ESPN, in late 2014, had already cut the show to a half-hour and moved its timeslot from 11PM to 5PM, but if the moves were meant to dull Olbermann's edge, they didn't succeed.note 

In the summer of 2015, news leaked that ESPN was going to pass on renewing Olbermann's contract. Olbermann signed off on July 24th, 2015 after a little less than two years on the air. ESPN maintains the move was not over content, but that the cost of the show was prohibitively expensive.note 

Some speculated that Olbermann could return to MSNBC, that his voice would be welcomed by many considering the upcoming 2016 US election cycle. Indeed, after making an appearance on ABC's The View in which he criticized Republican front-runner Donald Trump, Olbermann stated that he would be "coming out of retirement." In September 2016, he teamed up with GQ magazine for a bi-weeklynote  Web Video series called The Closer (no relation). These relatively short videos (usually less than ten minutes) echo the Special Comments of his Countdown days. After Trump won, the series was retitled The Resistance with Keith Olbermann. In the final episode of The Resistance, November 27, 2017, Keith declared that the Trump Admin would soon end, and he abandoned most political commentary (save for a snark here and there on Twitter) to return to ESPN, while continuing to raise money for rescue groups to save condemned dogs on NYACC's death row. In 2014, he branched out into voice acting, in the Netflix series BoJack Horseman, as the voice of Tom Jumbo-Grumbo, the blue whale news anchor on MSNBSea.

Three years later, on October 7, 2020, with the said Administration still in place and the 2020 election just weeks away, Keith returned to political commentary with a YouTube show entitled, of course, Worst Person in the World.

And in the wake of the COVID-19 Pandemic, Keith had some very strong messages about the Trump Administration's mishandling of the calamity and, more recently, the safety and necessity — and advantages — of vaccinations. "I went somewhere last night. I took the subway. I didn't wonder if I was gonna die. Not once. There's lots involved in deciding to get the vaccine but this is the bottom line: YOU DON'T THINK YOU'RE GONNA DIE."

In August of 2022, Keith returned to broadcasting Countdown, this time as a podcast. Included were a comment on the day's events, "Post-scripts to the news", a Sports segment, Worst Persons, Thurber Fridays, and "Things I Promised Not to Tell", a biographical look back on a point in his career. And he also highlights at least one dog slated to be killed at some kill shelter in America, so they can be saved, in "Every Dog Has His Day".

"Resist. Remove. Trope."

  • Adam Westing: Olbermann's character in BoJack Horseman, Tom Jumbo-Grumbo, is more-or-less an exaggerated parody of himself. Albeit, Olbermann is a human, and his character is a blue whale.
  • Amicable Exes: He is still close friends with his ex-girlfriend Katy Tur, a correspondent for NBC News, and is often the quickest to defend her.
  • Berserk Button: Hard to pick just one. Keith is infamous for his bad temper and perfectionism, which has cost him a lot of friendships. He gets worked up about pretty much everything, from bad plays in a baseball game to horrible political scandals, which sometimes makes it difficult to take all of his anger seriously.
  • Breakout Character: In the early days of his ESPN show, Keith would adopt a super-quiet, stereotypical golf announcer voice when voicing a golf highlight. Eventually, this persona picked up a name, Bob Slurm, and the show would regularly do golf highlights just to give Keith a chance to use the voice. Slurm also ended up branching out to other sports, like soccer and the Westminster Kennel Club Dog Show.
  • Depth Deception: In Real Life. The reason Keith doesn't drive is that he hit his head on a subway door in August 1980 while leaping onto a New York City Subway train. This head injury permanently upset his equilibrium, resulting in his avoidance of driving; instead, he takes public transportation, cabs, or limousines everywhere he goes.
  • Drama Queen: Ben Affleck played Olbermann in a Saturday Night Live hosting gig, leaning heavily on a portrayal of Olbermann as an over-the-top drama queen who turned every issue (including the co-op board at his condo refusing him permission to have a cat) into a grandiose melodrama. Olbermann admitted the sketch was Actually Pretty Funny, though he did make a mildly critical comment about the length of the sketch.
  • Fascinating Eyebrow: Pretty much the facial equivalent of Jon Stewart's "Go ooonnnnnn" — basically an invitation for the subject to continue digging themselves into a hole.
  • Friend to All Living Things/Heroes Love Dogs/Canine Companion: In an episode of The Resistance, Keith proudly claims to be a 'born-again' animal lover, marking the beginning of his life from the day he got his first dog in 2012note . He owns two Malteses, and he once cancelled an appearance on Bill Maher's program because one of the little guys was sick. He is constantly promoting cat and dog adoptions and rescue services on his Twitter and signal boosting alerts for lost pets. One of his deepest emotional crusades is the listing of "at risk" dogs (on his Tom Jumbo-Grumbo account) at the New York Animal Care Centers which have a very bad reputation for killing completely healthy, adoptable dogs and cats (and sickly, older and "behavior problem" dogs, many of whom are the much-maligned pit bulls) for little or no good reason. "You can pledge on any tweet and if the dog is rescued you will be tagged within two weeks with payment info for rescue. If he's killed you won't be contacted. Pledges go towards vetting/medical/training or anything else that's needed to help the dog." He has continued the pleas on his Countdown podcast in a segment called "Every Dog Has His Day".
    Unlike in so many areas of our current lives we can, individually, do something to defeat pain and death, if not for humans then for those who make our lives better.
    • In February 2021, he called out Ted Cruz for leaving his poodle Snowflake home while on vacation to Cancun and a trio of Newsmax pundits for mocking Joe Biden's dog Champ.
  • Game of Nerds: Keith is a huge baseball fan and historian. His baseball nerdery was so bad that his parents disallowed him talking baseball on every second day when he was eight. During his ESPN stint he often came up with some obscure minutia of baseball history ca. 1905 that he had researched. In short, there's a very good reason why Ken Burns turned to Keith for his Tenth Inning follow up to his documentary mini-series about the sport.
  • Large Ham: Sometimes intentional and sometimes not. Probably comes from being a sportscaster.
  • Sesquipedalian Loquaciousness: His rants can get there. The angrier he is, the more erudite he gets, to the point where you'd be forgiven for thinking he's an Aaron Sorkin character. (Naturally, Will McAvoy on The Newsroom is believed to be modeled after him, as Keith himself has acknowledged.)
  • Sharp-Dressed Man: Keith is a notably snappy dresser, and very careful about having his suits tailored to minimize his enormous size. He's not fat, he's just huge. Taken to a new level after partnering with GQ for The Closer/The Resistance. In 2019, having returned to ESPN, he now has a neatly trimmed beard.

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