"The Oscar" (1966)
Ruthless movie star Frankie Fane (Stephen Boyd) is desperate to win a you-know-what. You'd think the oddest thing about this famous stinker-oo would be the presence of so many Oscar winners in the cast: Ernest Borgnine, Broderick Crawford, Walter Brennan, Ed Begley. No, it's Tony Bennett, in his sole dramatic screen role, as Fane's best friend, Hymie Kelly. The improbability of the character's name is, alas, matched by the improbability of Bennett's performance.
Pictured from left: Stephen Boyd, Tony Bennet, and Milton Berle.