Olbermann's first TV job was at CNN, where he was hired in 1981. Upon being hired on June 5 this year by TBS to cover the fall MLB playoffs, Olbermann changed his Twitter avatar to a picture recalling the job: "Redskins' Victory Parade, a mere 30 years ago." To the left, a screengrab of a video of the correspondent excitedly reporting from Washington on the parade.
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Olbermann was part of WCVB TV's NewsCenter team for a year after being hired in 1984. He can be seen briefly at the end of this Channel 5 promo compilation.
Olbermann was hired by KTLA in 1985 and stayed at the L.A. network covering sports for three years. A year into his tenure, an L.A. Times TV critic wrote of the host: "Olbermann is a funny man, whipping those usually routine taped highlights into high comedy with a wonderfully caustic and refreshingly smart-alecky and irreverent style."
Olbermann joined CBS 2 in Los Angeles in 1988 and parted ways with the station in 1992. "Because of his wit and a clever writing style, Olbermann built a considerable following," the LA Times found at the time of his departure. "Others, however, found him arrogant and condescending." The image of the mustachioed anchor (left) is from a segment where he reported on the sartorial choices of L.A. Kings hockey team coach Robbie Ftorek.
Olbermann made a name for himself in sports news as the host of ESPN's Sportscenter along with Dan Patrick from 1992 to 1997. At the end of his contract, however, one ESPN official was quoted saying: "He didn't burn the bridges here, he napalmed them." He wrote a 1998 book in tribute to Sportscenter with Patrick titled The Big Show.
Olbermann was hired by MSNBC in 1997 to host The Big Show. Brian Williams, who was MSNBC's managing editor, said of the host: "They say you have to have 'it' to make it and to make a connection with viewers. He's got more of 'it' than many, many people I could name in the business." Olbermann grew disenchanted, remarking in 1998: The job would "make me ashamed, make me depressed, make me cry."
Olbermann was hired by Fox Sports Net in 1998 where he was billed in a promo (seen at left) as "Same Keith. New Network." He was fired in 2001 by Rupert Murdoch, who years later described the host as "crazy" at the time. Olbermann fired back: "he had to pay me $800,000 for the rest of 2001, and lord knows how many tens of millions I’ve helped MSNBC take out of his pocket ever since — so, who’s crazy?"
The anchor was hired in 2002 as a special contributor to NewsNight where he reported on MLB coverage. He's seen at the left during a segment with Anderson Cooper on Major League Baseball's contract negotiations.
In Spring 2003, Countdown with Keith Olbermann was announced on MSNBC. "He's edgy, he's got attitude, he's hip, he's clever, he's a good writer," MSNBC President Erik Sorenson said to the AP when he was hired. The show ran until January 2011, when he parted ways with the network on strained terms. "Every job he has ever had, he and the person he's working for end up hating each other," a former MSNBC colleague told The Hollywood Reporter in June 2011.
During his tenure with MSNBC's Countdown, Olbermann also began to contribute to NBC Sports' football coverage in 2007. His tenure as host of Sunday Night Football ended in 2010. Sources told The Hollywood Reporter at the time that the host's MSNBC bosses influenced the decision because they wanted his attention paid to Countdown.
After leaving MSNBC, Olbermann landed at Al Gore's Current TV with fanfare in February 2011. His arrival was supposed to herald the mainstreaming of the progressive network. Instead it ended with Olbermann's firing in March 2012 and a $50 million legal dispute that was resolved a year later.
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On June 5, Olbermann was announced as host for Turner on TBS' MLB postseason coverage. "Thanks to all who have sent good wishes on my new gig on MLB on TBS," he wrote on Twitter about the announcement. Turner Sports executive David Levy told The Hollywood Reporter after his hiring: "I think he realizes that he’s obviously burned some bridges out there in the marketplace."