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10. Hairspray (2007)
John Waters’s original 1988 cult film found new life on the Broadway stage in 2002 as a musical. The enthusiastic 2007 film adaptation of the musical boasts a talented cast, including Christopher Walken as Mr. Turnblad and a game John Travolta in drag, and a tongue-in-cheek attitude toward our mass culture’s rigid definition of beauty.
9. Guys and Dolls (1955)
Based on the Tony Award-winning stage version, this production was notable for casting “non-singer” Marlon Brando in the lead role of Sky Masterson—an action which supposedly annoyed cast mate Frank Sinatra, who played the smaller part of Nathan Detroit.
8. Chicago (2002)
Director Rob Marshall’s updated, Oscar®-winning version of the venerable Broadway show sticks closely to its theatrical predecessor, preferring traditional stage performances by the actors to more “cinematic” trickery.
7. West Side Story (1961)
A whirlwind of Broadway music and dance mixed with Shakespearian tragedy and teen angst, West Side Story won 10 of its 11 Oscar nominations. In addition, the film’s soundtrack became the highest-selling album ever up to the point of its release.
6. Hedwig and the Angry Inch (2001)
Following a successful off-Broadway run beginning in 1998, this film adaptation follows Hedwig, the East German transgender lead singer of a rock band, through the trials and tribulations of life before and after the fall of the Berlin Wall. Its honest, philosophical take on issues of transgender identity inspired its current cult following.
5. The Rocky Horror Picture Show (1975)
Similar to Hedwig, Rocky Horror still enjoys classic cult status in the midst of its thirty-plus years of limited theatrical release. A parody of terrible B-movies that revels in its references to other films, genres, and pieces of pop culture, its midnight showings often attract fans in costumes and become large-scale sing-alongs.
4. The Sound of Music (1965)
Who doesn’t know the words to “Do-Re-Mi”? This classic musical knocked Gone With the Wind (1939) out of top spot for all-time gross at the time of its release, and its soundtrack has never been out of print. Though some dislike its sugary tone, Julie Andrews and company bring sincerity to a plot that could have been gimmicky (despite its basis in real events).
3. Grease (1978)
Likewise, who doesn’t know the words to “Summer Nights”? Danny and Sandy’s happy-ending love story may not be the most original of all time, but the film’s nostalgic tone, sly wit and gleeful attitude toward teen romance give it a timeless feel that only increases on repeated viewings.
2. My Fair Lady (1964)
Audrey Hepburn and Rex Harrison star in this film, deemed the “perfect musical” by many critics. Though the story of Hepburn’s surprise winning of the role of Eliza Doolittle over Julie Andrews is now film industry legend (Andrews originated the role on Broadway), her lively performance was still almost nominated for an Oscar®—except her singing was dubbed, making her ineligible.
1. Cabaret (1972)
The ultimate display of theatrical talent — the legendary Liza Minnelli — is at the height of her powers in Cabaret, a tale set in Weimar Germany and shadowed by the rise of the Nazi Party. As the film explores the dark corners of sexuality, escapism, and the divide between fantasy and reality, it comments on not only the Germany of the time, but also on itself as a musical: as the film’s Master of Ceremonies says, “Come in, and leave your troubles outside!”—something every musical tries to offer.
Good list! I would have put Hairspray higher up the list though 
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