History Creator / KeithOlbermann

On July 17, 2013, Olbermann re-joined ESPN, prompting reactions of CueTheFlyingPigs 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 [[DomesticAbuse 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 fact, the move was perceived at the time as ''benefitting'' Olbermann, since the late-night time slot resulted in the show being bounced around the schedule or to ESPNEWS depending on when sports events on ESPN and [=ESPN2=] ended, making it hard for people who wanted to watch the show, and didn't care about its lead-in, to catch it.[[/note]]

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 Creator/{{ESPN}}'s ''Series/SportsCenter'' 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 Creator/AaronSorkin drama ''Series/SportsNight''. After disputes with management, he left in 1997, seemingly burning his bridges in the process, though he would remain friends with Patrick.

* AdamWesting: Olbermann's character in ''WesternAnimation/BoJackHorseman'' is more-or-less an exaggerated parody of himself. Albeit, Olbermann is a human, and his character is a humpback whale.

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 "Stories I Promised I Wouldn't 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".

* AdamWesting: Olbermann's character in ''WesternAnimation/BoJackHorseman'' is more-or-less an exaggerated parody of himself.

* DepthDeception: In RealLife. The reason Keith doesn't drive is that he hit his head on a subway door, and now has no depth perception when moving over 15 mph.

It was at this point Keith would make his first foray into non-sports news, as host of a primetime news show on Creator/{{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 scandal[[note]]A scandal Keith considers to be overblown and which he often mentions in a derisive way to point out how news had gone down the drain at this point in time[[/note]], causing Keith to quit and go back into sports, this time at Creator/{{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 Creator/{{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 ''Series/CountdownWithKeithOlbermann''. It found its voice as a left-wing {{foil}} to shows such as those found on Creator/FoxNewsChannel. 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. [[Series/TheOReillyFactor Bill O'Reilly]] was an early and frequent recipient of this award, and this led to a long and recurring feud between the two.

* FriendToAllLivingThings[=/=]HeroesLoveDogs[=/=]CanineCompanion: 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 2012[[note]]he also loves cats, but can't have any as he's allergic[[/note]]. He owns two Malteses, and he once cancelled an appearance on Creator/BillMaher's program because one of the little guys was sick. He is constantly promoting cat and dog adoptions and rescue services on his Website/{{Twitter}} and signal boosting alerts for lost pets. One of his deepest emotional crusades is the listing of "at risk" dogs (on his [[https://twitter.com/TomJumboGrumbo 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."

* SharpDressedMan: ''And how''. 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 BadassBeard.

* FriendToAllLivingThings[=/=]HeroesLoveDogs[=/=]CanineCompanion: 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 2012[[note]]he also loves cats, but can't have any as he's allergic[[/note]]. 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 Website/{{Twitter}} and signal boosting alerts for lost pets. One of his deepest emotional crusades is the listing of "at risk" dogs (on his [[https://twitter.com/TomJumboGrumbo 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."

* FriendToAllLivingThings[=/=]HeroesLoveDogs[=/=]CanineCompanion: In an episode of ''The Resistance'', he proudly claims to be a 'born-again' animal lover, marking the beginning of his life from the day he got his first dog in 2012[[note]]he also loves cats, but can't have any as he's allergic[[/note]]. 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 Website/{{Twitter}} and signal boosting alerts for lost pets. One of his deepest emotional crusades is the listing of "at risk" dogs (on his [[https://twitter.com/TomJumboGrumbo 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."

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''.

Some [[http://variety.com/2015/tv/columns/keith-olbermann-msnbc-leaves-espn-1201536388/ 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 Creator/{{ABC}}'s ''Series/TheView'' in which he criticized Republican front-runner UsefulNotes/DonaldTrump, Olbermann stated that he would be "coming out of retirement." In September 2016, he teamed up with ''GQ'' magazine for a bi-weekly[[note]]or more, if Keith feels like it[[/note]] WebVideo series called ''The Closer'' ([[Series/TheCloser 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 ''WebVideo/TheResistanceWithKeithOlbermann''. 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 Creator/{{Netflix}} series ''WesternAnimation/BojackHorseman'', as the voice of Tom Jumbo-Grumbo, the blue whale news anchor on [=MSNBSea=].

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

* AdamWesting: Olbermann's character in ''WesternAnimation/BojackHorseman'' is more-or-less an exaggerated parody of himself.

* DramaQueen: Ben Affleck played Olbermann in a Series/SaturdayNightLive 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 ActuallyPrettyFunny, though he did make a mildly critical comment about the length of the sketch.