Along the way, Brady meets Billy Montana ( Bruce Boxleitner) and the two become friends. Kenny Rogers stars as Brady Hawkes, the titular gambler, who embarks on a journey to meet Jeremiah ( Ronnie Scribner), the young son he never knew after Jeremiah sends him a letter. The show won a Best Edited Television Special Eddie Award and garnered two Emmy Award nominations (for cinematography and editing of a limited series). It was a ratings and critical success that has spawned four sequels. Kenny Rogers as The Gambler debuted on CBS on April 8, 1980. Main article: Kenny Rogers as The Gambler The Gambler Returns: The Luck of the Drawįilms Kenny Rogers as The Gambler (1980) Kenny Rogers as The Gambler, Part III: The Legend Continues Kenny Rogers as The Gambler: The Adventure Continues The Gambler Returns: The Luck of the Draw (1991).Kenny Rogers as The Gambler, Part III: The Legend Continues (1987).Kenny Rogers as The Gambler: The Adventure Continues (1983).The first four were directed by Dick Lowry while the last was directed by Jack Bender. The character was inspired by Rogers' hit single ' The Gambler'. The Gambler is a series of five American Western television films starring Kenny Rogers as Brady Hawkes, a fictional old-west gambler.