The Rise and Fall of Legs Diamond is a 1960 crime film directed by Budd Boetticher and starring Ray Danton, Karen Steele and Elaine Stewart.

The picture marked the film debut of Dyan Cannon and was nominated for an Academy Award for Best Costume Design for Howard Shoup.

Jack meets dance instructor Alice Shiffer, lies to her to date her and to steal a necklace from a jewelry store.

When he travels to Europe with Alice on a vacation, he sees in the newspaper that the New York underworld has changed with the National Prohibition Act.

He says he wanted to make a film like The Triumph of the Will ("the greatest picture I ever saw") "about one of the most despicable men of all time, Adolf Hitler.

"[2] From Howard Thompson of The New York Times: The unhealthy keynote of Warners' flashy screen portrait of the notorious Jack Diamond is that his "rise" is quite entertaining to watch ...

[5] The film was adapted as a musical titled Legs Diamond that debuted on Broadway at the Mark Hellinger Theatre on December 26, 1988, and it closed on February 19, 1989 after 64 performances and 72 previews.