How Kenny Rogers Went From Singing ‘The Gambler’ to Playing Him on TV

As singer Kenny Rogers told listeners in the country-music parable “The Gambler,” you’ve got to know when to hold ‘em, know when to fold ‘em, know when to walk away, and know when to run—which is exactly what he did when he took a gamble on starring in five TV movies based on his hit 1978 recording of the song.

Turns out, it was Ken Kragen, Rogers’ manager, who pitched the idea of a Gambler movie to CBS. “He attended an awards program, found two CBS executives backstage, and cornered them,” Rogers wrote in his 2011 memoir, Luck or Something Like It. “He had made up a big poster of me as ‘The Gambler’ and unfurled it for them to see. He had a one-line pitch. ‘Don’t you think this guy needs to be in a movie?’ he asked them. The executives apparently agreed to a movie deal on the spot, sticking out their hands and saying, ‘Done!’ As incredible as it sounds, that’s how simple it was.”