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.

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In prohibition-era Chicago, the corrupt sheriff and Guy Gisborne, a south-side racketeer, knock off the boss Big Jim. Everyone falls in line behind Guy except Robbo, who controls the north side. Although he’s out-gunned, Robbo wants to keep his own territory. A pool-playing dude from Indiana and the director of a boys’ orphanage join forces with Robbo; and, when he gives some money to the orphanage, he becomes the toast of the town as a hood like Robin Hood. Meanwhile, Guy schemes to get rid of Robbo, and Big Jim’s heretofore unknown daughter Marian appears and goes from man to man trying to find an ally in her quest to run the whole show. Can Robbo hold things together?

The original characters from the first Cannonball Run movie compete in an illegal race across the country once more in various cars and trucks.

A cross-country road race is based on an actual event, the Cannonball Baker Sea to Shining Sea Memorial Trophy Dash, organized by Brock Yates to protest the 55 mph speed limit then in effect in the U.S. The Cannonball was named for Erwin G. “Cannonball” Baker, who in the roaring 20’s rode his motorcycle across the country. Many of the characters are based on ruses developed by real Cannonball racers over the several years that the event was run.

Taxi dancer Charity continues to have Faith in the human race despite apparently endless disappointments at its hands, and Hope that she will finally meet the nice young man to romance her away from her sleazy life. Maybe, just maybe, handsome Oscar will be the one to do it.

Little known actor, Jack Noah, is working on location in the dictatorship of Parador at the time the dictator dies. The dictator’s right hand man, Roberto, makes Jack an offer he cannot refuse.. to play the dictator. Jack’s acting skills fool the masses but not close friends and employees of the dictator.