Tony Curtis, star of Some Like it Hot and The Defiant Ones, died Wednesday at 85 years old. The actor who started his career as a matinee idol and made his greatest contribution to comedy by dressing in drag played virtually every kind of role available in Hollywood during the 50s and 60s, from the smarmy agent Sidney Falco in The Sweet Smell of Success to Arabian prince Kashma Baba in Son of Ali Baba, one of his first starring roles. He was nominated for an Oscar once, for The Defiant Ones, in which he and Sidney Poitier played a pair of criminals escaping from a chain gang while still handcuffed to one another.

His acting career petered out toward the end of the 60s, though he still made guest appearances on television as recently as a 2004 episode of Hope and Faith. Though Curtis will remain primarily an icon of an earlier era of Hollywood, his performance alongside Some Like It Hot remains iconic, a cornerstone of American comedy and, with Curtis particularly, a master class for comedians in how to look attractive and ridiculous at the same time. From the fake Cary Grant accent and coke bottle glasses to his stunned reaction when Lemmon comes home singing about his engagement to man, Curtis pulls off the magic trick of playing the straight man while wearing a dress and heels.

For more on Curtis and his astonishing life in Hollywood (including fathering actress Jamie Lee Curtis), the Los Angeles Times has an excellent obituary of the actor born Bernard Schwartz in the rough New York City of the 1920s.

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