Skip Bayless addresses ‘fairly prominent’ role in Cowboys documentary, claims it’ll outdo ‘The Last Dance’

The trailer features numerous legendary figures who were around the Dallas Cowboys in the 1990s. That includes Jerry Jones, Jimmy Johnson, Emmitt Smith, Michael Irvin, Troy Aikman, and Deion Sanders.

Skip Bayless has long since been associated with the Dallas Cowboys. In the 1990s, he wrote several books on the legendary franchise. While working as a columnist in Dallas, Bayless wrote three books on the Cowboys, including God’s Coach: The Hymns, Hype and Hypocrisy of Tom Landry’s Cowboys, The Boys: The Untold Story of the Dallas Cowboys’ Season on the Edge, and Hell-Bent: The Crazy Truth About the “Win or Else” Dallas Cowboys.

Notably, Bayless’ book Hell-Bent got into some of the issues within the Cowboys. In particular, it discussed the friction between quarterback Troy Aikman and head coach Barry Switzer. That, unsurprisingly, led to some tension between Bayless and Aikman over the years.

Beyond just predicting that he’ll play a major role in the documentary, Skip Bayless also thinks that it’s going to outdo another 1990s sports documentary, The Last Dance. Covering the Chicago Bulls dynasty, The Last Dance was a sensation during the pandemic when there were otherwise limited sports options.

“I believe this documentary will be even bigger than The Last Dance documentary and the ’98 Bulls,” Bayless said. “It did have the advantage of dropping obviously early in the pandemic. But I believe Jerry’s doc, America’s Team’s doc, will be bigger.”

That’s a difficult bar to clear, but Skip Bayless certainly seems excited about America’s Team: The Gambler and His Cowboys. The first episode is set to air on August 19, 2025, just ahead of the upcoming NFL season.