By Joe McGovern
February 01, 2017 at 05:11 PM EST

In its 88 years, the Academy Awards have given the top prize to a musical 10 times. That number is potentially going to dial up to 11 on Feb. 26, when the 14-nomination-strong La La Land is favored to triumph. If so, director Damien Chazelle’s film will be only the second musical to win Best Picture in the last 50 years.

In the latest issue of Entertainment Weekly, we journey back 65 years to appreciate Vincente Minnelli and Gene Kelly’s game-changer An American in Paris. The Best Picture winner from 1951 is, according to Chazelle, “such a stunner. It’s an awesome example of how daring some of those old musicals really were.”

And its influence is felt not only in La La Land — Chazelle happily admits that the concept for his film’s dream ballet ending was pillaged from An American in Paris‘ finale — but also in decades of movie musicals that followed. Here we rank the 10 Best Picture-winning musicals, from true showstoppers to summer stock.

1. West Side Story (1961)

Everett Collection

Directed By: Robert Wise and Jerome Robbins
Oscars Won: 10
Rotten Tomatoes: 94%

Shakespeare’s Romeo and Juliet was updated to New York City in the 1950s — and transformed into one of the greatest Broadway and movie musical masterpieces of all time. Pick any scene — “Maria,” “America,” “Tonight” or the snapping prologue — and you’re experiencing a song and dance classic.

2. The Sound of Music (1965)

Everett Collection

Directed By: Robert Wise
Oscars Won: 5
Rotten Tomatoes: 86%

The hills are alive…forever. Rodgers and Hammerstein’s enchanting 1959 Broadway show was brought to vivid life by West Side Story director Robert Wise and Julie Andrews, six months after the release of Mary Poppins. During its initial release, it passed Gone With the Wind to become the highest-grossing film of all time, eventually spawning a live TV version (in 2013) and millions of tourist trips to Austria.

3. My Fair Lady (1964)

Everett Collection

Directed By: George Cukor
Oscars Won: 8
Rotten Tomatoes: 96%

Best Actor winner Rex Harrison delivers one of the great leading man musical performances of all time as Henry Higgins, who reforms the poor, guttural Eliza Doolittle (Audrey Hepburn) into a refined British woman. Hepburn certainly has the charm to pull off “I Could Have Danced All Night,” though in a neat bit of Oscar trivia, Julie Andrews (the original Eliza on Broadway, passed over for the film) won that year’s Best Actress for Mary Poppins.

4. An American in Paris (1951)

Everett Collection

Directed By: Vincente Minnelli
Oscars Won: 6
Rotten Tomatoes: 95%

If some stretches of Minnelli’s tribute to Gershwin and the French capital feel dated, that has nothing to do with the charisma and athleticism of choreographer and star Gene Kelly. First he woos Leslie Caron along the Seine and then takes the audiences’ hand for one of the most ambitious finales of any musical — a 17-minute stunner. Here’s the sexiest piece.

5. Chicago (2002)

David James

Bob Fosse, John Kander and Fred Ebb’s prison satire came to life in razzle-dazzle style. Some of the songs play onscreen like music videos, but the central narrative idea — which contrasts the harsh realities of a murderess’ life with her fantasies — is a daring conceit. And audiences got it. The film earned $171 million, making it the most popular musical in decades.

Directed By: Rob Marshall
Oscars Won: 6
Rotten Tomatoes: 86%

For more Oscars coverage, pick up the new issue of Entertainment Weekly, on stands now, or buy it here — and subscribe for more exclusive interviews and photos, only in EW. 

6. Oliver! (1968)

Everett Collection

This big-hearted adaptation of Charles Dickens’ Oliver Twist was the fourth musical of the 1960s to win Oscar’s highest honor — and maybe the corniest. “Food, Glorious, Food” is a terrific opening number, but the production lacks Dickens’ bite. The next year’s Best Picture winner was the X-rated Midnight Cowboy — and Oliver! stands as a fascinating blast of family entertainment before the Academy embraced the dark side.

Directed By: Carol Reed
Oscars Won: 5
Rotten Tomatoes: 81%

7. Going My Way (1944)

Everett Collection

Directed By: Leo McCarey
Oscars Won: 7
Rotten Tomatoes: 77%

Actors Bing Crosby and Barry Fitzgerald both won Oscars as New York City priests in conflict over how to run their parish. Songs include the wondrous “Swinging on a Star,” but the film, more than seven decades later, is cloyingly sweet and too sentimental by half.

8. Gigi (1958)

Everett Collection

Directed By: Vincente Minnelle
Oscars Won: 9
Rotten Tomatoes: 77%

Gigi introduced the world to “Thank Heaven for Little Girls,” and swept all nine Oscars it was nominated for, but the story is simply flat as a crepe. The scenery is bright and lush, but the adaptation Colette’s 1944 French novella — a naughtier version of Pygmalion, the basis for My Fair Lady — contains none of its source material’s bite.

9. The Great Ziegfeld (1936)

Everett Collection

Directed By: Robert Z. Leonard
Oscars Won: 3
Rotten Tomatoes: 65%

Starring William Powell as Broadway impresario Florenz Ziegfeld, Jr., this lavish three-hour bio-musical was considered a standard bearer in the 1930s. Some of the song and dance sequences (like this one) still impress, but the dramatic scenes are bloated and melodramatic. Luise Rainer won Best Actress for a particularly overcooked performance.

10. The Broadway Melody (1929)

Everett Collection

Directed By: Harry Beaumont
Oscars Won: 1
Rotten Tomatoes: 35%

The first film with recorded dialogue (The Jazz Singer) was a musical; so was the first Best Picture winner with recorded dialogue. Neither has aged well. This story of two dancer sisters was victorious at the 2nd Academy Awards. Though it was considered innovative in its day (especially for one Technicolor sequence), the production is mostly a filmed theater piece. And quite a slog to sit through nowadays.

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