His younger brother Rick Bayless carried on the family tradition and became a chef, restaurateur and television personality.

At the urging of one of his English teachers, Bayless became the primary sports columnist for the school newspaper his junior and senior years.

There, he was best known for investigative stories on the Los Angeles Dodgers' clubhouse resentment of "golden boy" Steve Garvey and his celebrity wife Cyndy, and on Rams owner Carroll Rosenbloom's behind-the-scenes decisions to start different quarterbacks each week.

Bayless won the Eclipse Award for Outstanding Newspaper Writing in 1977 for his coverage of Seattle Slew's Triple Crown victory.

In 1994, he became one of the original investors in the Fort Worth radio station KTCK ("the Ticket"), and hosted The Skip Bayless Show from 6–9 a.m. weekdays from 1994 to 1996.

Soon thereafter, Bayless began co-hosting a weekend show on ESPN Radio with former SportsCenter anchor Larry Beil, which aired until 2004, when he moved full-time into television.

In 1989, Bayless joined host Dick Schaap as a panelist on ESPN's The Sports Reporters, and over the next decade, he was a regular on the Sunday morning show.

In 1992, Bayless became a member of the original debate team on NFL Prime Monday's "Knights of the Roundtable" segments with Mitch Albom and Michael Wilbon.

[citation needed] In 2001 and 2002, Bayless appeared regularly on Jim Rome's show on Fox Sports Net, The Last Word.

[citation needed] ESPN hired Bayless full-time in 2004 to team up with Woody Paige of The Denver Post in daily debate segments called "1st and 10" on ESPN2's Cold Pizza, and to write columns for ESPN.com.

[citation needed] On April 26, 2016, it was reported that Bayless had parted ways with ESPN, and would be moving to Fox Sports after his contract expired in August.

[25] Bayless is known for criticizing LeBron James and Aaron Rodgers and praising Tom Brady in both First Take and Skip and Shannon: Undisputed.

"[30] The tweet was called out by several high-profile sports figures such as former quarterback Robert Griffin III[31] and former wide receiver Dez Bryant.

[6][37] On January 5, 2025, Bayless was listed as a defendant in a lawsuit filed by former Fox Sports hairstylist Noushin Faraji against the network.

[38] Along with ESPN colleagues Woody Paige and Jay Crawford, Bayless had a cameo role in the 2006 film Rocky Balboa.

He appeared in the 2010 ESPN 30 for 30 film, Pony Excess, about the Southern Methodist University football scandal involving gross violations of NCAA rules and regulations.

[40] In 2012, he received two honors: he was nominated for a Sports Emmy Award in the category of Outstanding Sports Personality, Studio Analyst,[41] and was the co-recipient with DJ Steve Porter of a Webby People's Voice Award in the category of Video Remixes/Mashups for "All He Does Is Win", Porter's mashup of clips of Bayless passionately defending oft-maligned quarterback Tim Tebow.