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.”

And it was that simple: Rogers was on screen and in character as The Gambler less than a year and a half after the single first debuted.

Read on for a look back at Rogers’ 14-year career as gambling man Brady Hawkes—and whether his costars thought the series ever ran out of luck.

Kenny Rogers as The Gambler (1980)

In the first Gambler movie, Rogers debuted the character of card sharp Brady Hawkes, who connects with Jeremiah Hawkes (Ronnie Scribner), the son he never knew he had. And with the help of poker-playing whippersnapper Billy Montana, played by Bruce Boxleitner, Brady saves the boy and his mother from the clutches of an abusive casino owner.

“The poster that Ken concocted turned into a critical and ratings smash TV movie, expertly directed by Dick Lowry,” Rogers wrote in his memoir. “On its first airing on CBS, it got a 50 share of everyone watching TV in America, becoming the highest-rated TV movie of all time. It went on to win two Emmys and set the stage for four sequels.”

Kenny Rogers as The Gambler: The Adventure Continues (1983)

The second installment ofThe Gambler series sees Brady, Billy, and young Jeremiah (now played by Charles Fields) traveling to San Francisco for a gambling event. But then a criminal gang intercepts the train and takes Jeremiah hostage…

Joining the action in The Adventure Continues is Linda Evans in the role of bounty hunter Kate Muldoon. “In the film, I ride, shoot, and fight, which is quite a change of pace from Krystle Carrington, my character in Dynasty,” Evans told The Birmingham News.

Evans also had to sing a song for the production, which was “the biggest fear” of her life, she said. “I studied for months with a special instructor, which helped a great deal,” she said. “But this was the first time I ever actually had to do it — and with Kenny Rogers, one of the world’s most popular singers, standing on the set.”

Kenny Rogers as The Gambler, Part III: The Legend Continues (1987)

Brady and Billy help protect a Sioux tribe from a government threat in the threequel, which also featured George Kennedy as a Dakota Territory army commander, Linda Gray as a schoolteacher, and Charles Durning as a U.S. senator trying to appropriate 90 million acres of Native-owned land.

“It’s a lighthearted adventure, although this time we do play against a historical backdrop, the Ghost Dance, and the events leading up to the Wounded Knee massacre in the 1880s, the death of Sitting Bull, and the revenge of the 7th Cavalry,” Boxleitner told the Associated Press. “I don’t want to say we’re preaching. We all know the Indians got ripped off.”

The Gambler Returns: The Luck of the Draw(1991)

In the fourth film, and the only one to air on NBC instead of CBS, Brady attends another San Francisco gambling event and runs across other legendary Western figures. Cameos include Gene Barry back in his Bat Masterson role, Hugh O’Brian as the title character from The Life and Legend of Wyatt Earp, Clint Walker as Cheyenne Bodie from Cheyenne, and James Drury reprising his role as The Virginian.

Plus, Reba McEntire gets star billing in her role as madame Burgundy Jones.

“Reba’s success in country music, her Oklahoma roots, and her great riding ability were a perfect fit for us,” Rogers wrote in his memoir. “Reba was right at home in the saddle and welcomed the chance to show her ability. She had been a barrel rider in some Oklahoma rodeos when she was younger and still had all her skills.”

Gambler V: Playing for Keeps (1994)

The final Gambler outing has Brady rescuing Jeremiah (now portrayed by Kris Kamm) from the influence of outlaws Butch Cassidy (Scott Paulin) and the Sundance Kid (Brett Cullen). Martin Kove, Dixie Carter, and Loni Anderson all show up, as does a 20-year-old Mariska Hargitay.

The film also featured the brief return of Billy, after Boxleitner sat the fourth movie out because of a falling-out with Rogers and the Gambler team. Boxleitner told Newsweek in 2020 that Rogers called him to make amends and invite him to Playing for Keeps. “Suddenly, I’m being picked up at the airport in Vegas, and it’s Kenny behind the wheel, and we go shopping for lawn chairs and garden gnomes,” he recalled. “People are looking at Kenny with that hair and voice, and they’re like, ‘Oh my God, it’s The Gambler!’”

Boxleitner added: “I’ve done a lot of series in my career; The Gambler was my favorite. When Kenny called, I answered and said, ‘Where and when?’ People say John Wayne played John Wayne. Well, Kenny was like that. He wanted to play the best damn Kenny Rogers, and that’s what he did.”