Keith Olbermann was born on January 27, 1959, in New York City and studied communication at Cornell University, graduating in 1979. He began his career in sports radio and wire reporting before CNN hired him as a sports correspondent in 1981. He went on to co-host ESPN’s SportsCenter from 1992 to 1997, winning the California Associated Press’s Best Sportscaster award three times along the way.

Olbermann moved into political commentary in 2003, launching Countdown with Keith Olbermann on MSNBC. The nightly show built its identity around Olbermann’s editorializing and his running on-air feud with Fox News’ Bill O’Reilly. He left MSNBC abruptly in January 2011 after negotiating an exit deal the network hadn’t expected, then relaunched Countdown at Current TV five months later. However, the new version drew a fraction of his old audience before ending in 2012.

Since leaving television, Olbermann has moved between ESPN, GQ’s website, and his own outlets, most recently reviving Countdown as a daily podcast in 2022. He remains an outspoken presence online, including a widely covered 2025 exchange with fellow host Bill Maher over Maher’s meeting with President Trump. Olbermann continues to record Countdown from outside the television industry he spent four decades in.