Dean Martin had a laid-back charm that made him successful in everything from big-screen comedies to television variety shows to live acts in Las Vegas. Filmmaker Tom Donahue explores Martin’s varied career, including his complicated relationships with Jerry Lewis, Frank Sinatra, Sammy Davis Jr, and others. We hear from admirers such as critic Gerald Early, actor Jon Hamm, and Hip-Hop artist RZA who testify to Martin’s enduring mystique.

Russ Richards is a TV weatherman and local celebrity on the verge of losing his shirt. Desperate to escape financial ruin, he schemes with Crystal the TV station's lotto ball girl to rig the state lottery drawing. The numbers come up right, but everything else goes wrong as the plan starts to unravel and the game turns rough.