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.

The top brass at a radio station believe their popular new star singer is paying more attention to his love life than to his career.

Fleischer Studios 'Screen Song' of "When Yuba Plays the Rumba on the Tuba".

The Mills Brothers perform the title song with Bouncing Ball; cartoon animals load and sail the cargo ship 'Dinah Lee' to Mills music.

American Civil War, 1862. After the disaster of the Second Battle of Bull Run, Major Allen, chief of the Secret Service of the Union, asks actress Gail Loveless to become one of his operators and infiltrate enemy territory.

Beverly Ross, the switchboard operator at a local radio station, jumps at the chance to be the DJ for an early morning show before the soldiers at a nearby army camp assemble for reveille. Beverly, with her modern music, camp bulletins and chatter, is a hit with the soldiers. Beverly's younger brother and his two buddies are soldiers at the camp. The buddies vie for Beverly's attentions.

A failed poet ends up becoming a gag writer for a bombastic comedian.

Unscrupulous agent Rush Blake makes singing waiter Buddy Clayton a big radio star while Peggy Cornell, who has lost her own radio show, helps Buddy.