Sail a Crooked Ship is a 1961 American black-and-white comedy heist film starring Robert Wagner, Dolores Hart, Carolyn Jones, Frankie Avalon, Ernie Kovacs and Frank Gorshin.

[2] Sail a Crooked Ship was Kovacs' last movie, released shortly before he was killed in a car crash.

Hart's other 1961 film, Francis of Assisi, inspired her to retire from acting two years later and become a Roman Catholic nun.

When Gilbert Barrows (Robert Wagner) disobeys his boss and tries to refit an old Liberty Ship for cargo use instead of scrapping it, he inadvertently puts it into the hands of a colorful group of crooks led by good-hearted screw-up Bugsy G. Fogelmeyer (Ernie Kovacs) and brainy sociopath George M. Wilson (Frank Gorshin).

The crooks plan to use the ship to make their getaway after they pull a bank robbery in Boston, and they kidnap Barrows and his girlfriend Elinor Harrison (Dolores Hart) – his boss's daughter – to prevent leaving any witnesses behind.

He and then-wife Natalie Wood formed their own company, Rona Productions, which signed a three picture deal with Columbia for Wagner's services.