5 of 10
The legendary superstar followed in a grand tradition of "Fox Blondes" that included Alice Faye, Betty Grable and June Havoc. Though she did fine dramatic work during her short-lived career, most notably in her final feature, 1961's "The Misfits," Monroe is best known for her picture-perfect comedic timing. She made a great dumb blond in the 1953 comedies "Gentlemen Prefer Blondes" and "How to Marry a Millionaire." Of course, she became the object of every man's desires when her white dress flipped up thanks to the subway grating on a New York sidewalk in 1955's "The Seven Year Itch."
Monroe grew only stronger as a comedic actress after heading to New York and studying the Method with Lee Strasberg. And in her first post-Strasberg film, 1956's "Bus Stop," she's funny, winsome and poignant as Cherie, a young entertainer who is traveling by bus to get to "Hollywood and Vine." Her performance of "That Old Black Magic" will make you laugh and cry at the same time. And despite dealing with enormous personal problems and demons, she is absolutely spot-on as Sugar Kane in Billy Wilder's 1959 comedy, "Some Like It Hot." She tragically died of a drug overdose in 1962 at the age of 36.