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Foolish life insurance salesman Milford Farnsworth (Bob Hope) commits his biggest blunder yet when he unwittingly offers a six-figure policy to notorious gunslinger Jesse James (Wendell Corey). Furious, his boss orders him to repurchase the policy. James, however, parries Farnsworth's attempts with ease, robbing and humiliating him. But when James' latest scheme pairs the patsy with the bandit's sweetheart, Cora Lee Collins (Rhonda Fleming), Farnsworth and Cora begin falling in love.