Its 1960, and Frank Sinatra is at the height of his power and influence in Hollywood. Bobby Blaine, a peripheral member of the Rat Pack, chafes under the singers egomania and bullying. He tries to land roles without Sinatras help and encounters only failure, until he is asked to do one last favor: pick up Marilyn Monroe in Reno, where she is having a nervous breakdown trying to finish "The Misfits," and deliver her into the clutches of Sinatras Mafia pals at the Cal-Neva Lodge. Bobby hires Gene, a 20-year-old would-be beatnik, as his driver. Gene falls in love with a Mexican-American motel...