He was a sports correspondent for CNN and for local TV and radio stations in the 1980s, winning the Best Sportscaster award from the California Associated Press three times.

[17] It is described as a news-driven show featuring his trademark "Special Comment" political analysis, "The Worst Persons in the World" segment, and readings from the works of humorist James Thurber.

[36] Early in 1997 Olbermann was suspended for two weeks after he made an unauthorized appearance on The Daily Show on Comedy Central with then-host and former ESPN colleague Craig Kilborn.

He replaced Matt Winer, who had been in this role since his departure from ESPN to join the Turner Sports family, and was originally supposed to host the show with TBS' Dennis Eckersley.

The two-year contract would allow him to deviate from the topic of sports into realms such as "pop culture and current events",[50] as well as politics, which was a right Olbermann claimed he did not intend to exercise.

In addition, Olbermann wrote a weekly column for Salon.com from July 2002 until early 2003,[63] worked for CNN as a freelance reporter,[25] and was a fill-in for newscaster Paul Harvey.

Former Los Angeles Times television critic Howard Rosenberg stated that "Countdown is more or less an echo chamber in which Olbermann and like-minded bobbleheads nod at each other.

In a technique similar to that of former CBS News anchor Walter Cronkite in connection to the Iran Hostage Crisis,[68] for the last six years of the program, Olbermann closed every show by announcing the number of days passed since President George W. Bush had declared the end of "major combat operations" in Iraq under a banner that read "Mission Accomplished" (May 1, 2003).

[70] Olbermann co-anchored, with Chris Matthews, MSNBC's coverage of the death of fellow NBC News employee Tim Russert on June 13, 2008.

[72] During the 2008 U.S. presidential election, Olbermann co-anchored MSNBC's coverage with Chris Matthews until September 7, 2008, when they were replaced by David Gregory after complaints from both outside and inside of NBC that they were making partisan statements.

[73] This apparent conflict of interest had been an issue as early as May 2007, when Giuliani campaign officials complained about his serving in dual roles, as both a host and a commentator.

[4][82][83] The rivalry continued when in 2006 at Television Critics' Association in California, Olbermann donned a mask of O'Reilly and made a Nazi salute, leading to a letter of protest from the Anti-Defamation League.

[84][85][86] In an article on "perhaps the fiercest media feud of the decade", The New York Times' Brian Stelter noted that in early June 2009 the "combat" between the two hosts seemed to have abruptly ended as a result of instructions filtered down to Olbermann and O'Reilly from the chief executives of their respective networks.

In response, on November 5, MSNBC President Phil Griffin suspended him indefinitely without pay for violating a network policy which required employees to obtain approval from management before making political contributions.

[90][91] An online petition calling for his reinstatement received over 250,000 signatures;[92] two days after the suspension began, Griffin announced that Olbermann would return to the air on November 9.

The blog featured political commentaries by Olbermann—including viral video versions of Countdown's "Special Comment" and "Worst Person" segments, as well as photographs of his outings at professional baseball games.

According to Politico, the fact Olbermann had been rendered unemployable as a result of the dispute, factored heavily during settlement negotiations between his attorneys and representatives from CurrentTV.

[107] In mid-October 2017, Penguin Random House issued a hardcover book by Olbermann, Trump Is F*cking Crazy (This Is Not a Joke), consisting of 50 essays based on The Resistance commentaries.

Olbermann has made several acting appearances either as himself or simply as a sports/newscaster, most notably as Tom Jumbo-Grumbo (a blue whale newscaster on the MSNBSea network) in several episodes of BoJack Horseman.

[114] In January 2007, The Washington Post's Howard Kurtz wrote that Olbermann was "position[ing] his program as an increasingly liberal alternative to The O'Reilly Factor.

"[115] Much of the program featured harsh criticism of prominent Republicans and right-leaning figures, including those who worked for or supported the George W. Bush administration, 2008 Republican presidential nominee Senator John McCain and running mate Governor Sarah Palin,[73][116] and rival news commentator Bill O'Reilly, whom Olbermann has routinely dubbed the "Worst Person in the World".

[5] During the 2008 Democratic Party primaries, Olbermann frequently chastised presidential aspirant Hillary Clinton for her campaign tactics against her principal opponent, Senator Barack Obama, and made her the subject of two of his "special comments".

[121] Before the 2010 Massachusetts special election, Olbermann called Republican candidate Scott Brown "an irresponsible, homophobic, racist, reactionary, ex-nude model, Tea Bagging supporter of violence against women, and against politicians with whom he disagrees".

[124] The next night, Olbermann chose to "double down", as The Huffington Post's Danny Shea described it,[125] on his criticism of Brown by adding the word "sexist" to his original description of the Republican candidate.

"[125] Olbermann accused the Tea Party movement of being racist due to what he views as a lack of racial diversity at the events, using photos that show overwhelmingly white crowds attending the rallies.

Olbermann declined the invitation, citing his father's prolonged ill health and hospitalization and stated that the network has minority anchors, contributors and guests.

[126] In October 2020, Olbermann called for supporters and what he described as "enablers" of Donald Trump, including United States Supreme Court nominee Amy Coney Barrett and conservative political commentator Sean Hannity, to be "prosecuted" and "removed from our society".

[131] On his February 14, 2008, "Special Comments" segment, Olbermann castigated Bush for threatening to veto an extension of the Protect America Act unless it provided full immunity from lawsuits to telecom companies.

[132] In a special comment on May 14, 2008, Olbermann criticized Bush for announcing that he had stopped playing golf in honor of American soldiers who died in the Iraq War.

[137] Olbermann has dated several women involved in politics and journalism, including Katy Tur, Laura Ingraham, Kyrsten Sinema and Olivia Nuzzi.