Ranking the 9 Best Picture Musical Winners

Scene from La La Land

This Sunday marks the event that everyone has been waiting for: Oscar Sunday. While everyone makes their last minute predictions (I will be sharing mine tomorrow), there is one agreed consensus: this is La La Land's year for Best Picture. The musical has received unanimous acclaim for its spectacular craft. Provided nothing changes and it wins, it will join a small list of musicals that have achieved an honor that only 88 movies have achieved so far. What's more surprising is that there's been only nine musicals to have won the category despite being one of Hollywood's most iconic genres. Which is the best of the bunch? Click on to find out, and come back on Monday, provided that it wins, to find out where La La Land falls on the list of the best Oscar-winning Best Picture musicals.

1. West Side Story

Not only is the story of Sharks vs. Jets one of the best movie musicals ever conceived, it is one of the greatest Best Picture winners period. With an incredible soundtrack that features such standards as "I Feel Pretty" and "Tonight," the film is a testament to what the visual medium can bring to a song and dance show. It also features some of the best choreography, direction, and set design of any musical ever nominated; managing to update the traditional Hollywood style with realistic sets. It may just be a creative and socially relevant twist on Shakespeare, but who can complain when it looks and sounds this good?

2. My Fair Lady

Much like West Side Story, My Fair Lady is one of the musicals that set the bar for how contemporary stories could be told. The story is a fascinating dissection of how language unites and isolates us while exploring its relation to class. The film also features excellent performances by Audrey Hepburn and Rex Harrison; both of whose chemistry makes for a delightful butting of heads. It's hilarious. The songs are unforgettable. The costumes are some of the best out there. Most of all, it's a story that has continued to resonate through pop culture with it rich thematic subtext while also featuring one of the greatest final lines in film history: "Eliza, where the devil are my slippers?"

3. Chicago

The most recent musical to win Best Picture may also be the most underrated. It's story of jazz-era crime is popping with life and is given an extra touch of wonder thanks to director Rob Marshall's showmanship. Sure, this is a Bob Fosse story lacking his cinematic touch, but it's pretty close to the next best thing. With great sets that transcend the lush grandiosity of the stage show, it presents each number with a life that more than warrants its place in history as one of the three 21st century musicals to revive the genre (the others being Moulin Rouge! and Dancer in the Dark). Still, this is probably the most lovingly nostalgic of the bunch without it being a bad thing. Thankfully the songs are just as popping as the sets and costumes.

4. An American in Paris

It was one of the musicals that defined the MGM era with its vibrant sets, memorable songs, and the magic of great actors who could also dance. Everything about director Vincente Minnelli's style is on display here and it is exuding with earnest enthusiasm. It may lose some points for how silly and fantastical many elements look, but it's part of what defines movie magic. Anyone who has seen the film is likely to remember Gene Kelly's excellent dancing as well as the breathtaking dance montage that comes towards the end of the film. This is what many think of when they think of old school musicals, and that's a pretty great honor to have. 

5. The Broadway Melody of 1929

Along with being the first musical to win Best Picture, it was also the first talkie. It may have a lot of detrimental elements when compared to every other winner, but it still has the heart and influence to spare. Its camerawork may be a little staid and the acting a little flat, but it still has the enthusiasm of the first era of Hollywood musicals and one of the few winners here to also spawn several sequels. While it deserves points for being the first in a long line of winners, it holds up on its own as an innovative and exciting look at how far musicals have come in the almost nine decades since it won. 

6. Going My Way

The one thing that musicals have a strong gift for is displaying the charisma of Hollywood's most charismatic. Anyone familiar with cinema of the 1940's will know the impact that Bing Crosby had both as an actor and singer. There's few films that embody this better than Going My Way, which shows him playing a hip young priest who gets the baseball players to form a choir. It also features one of his most iconic hits ("Swinging on a Star"), which only adds to the allure of this essentially one man show. The sequel (The Bells of St. Mary's) would also go on to get a Best Picture nomination, which just goes to show just how unstoppable and great Crosby was in his heyday.

7. Oliver!

This musical epic updates Charles Dickens' "Oliver Twist" with song and dance that keeps things jaunty. What is probably the most impressive/unfortunate part of its legacy is that it is the only film to ever win Best Picture with a G rating. If nothing else, it makes Oliver! the only musical on this list that is appropriate for all ages. Still, it's not a bad thing as it features tons of fun songs, great set design, and solid direction from Carol Reed. It may fall at times on the cornball side of things, but nobody can deny that it still has the wonder and excitement, much like its iconic source material, that brings these iconic characters' story to life.

8. The Sound of Music

Yes, it has an iconic soundtrack. Yes, one could argue that it's among Julie Andrews' most beloved roles ever. However this fictionalized account of the Von Trapp family of musicians has very little else to offer. It's a silly, somewhat sterilized, account of World War II that features the nicest Nazis in history. Even with West Side Story's director Robert Wise bringing his gift to the film, it still is padded with too much material and inevitably falls under the pressure of its own minimal story. Don't let the great soundtrack fool you, the rest of the film is a tad dull with many of the songs lacking any narrative progression to the story. If you must have a good WWII musical about performers and Nazis, just watch Cabaret instead.

 9. Gigi

Of every musical to ever win, Gigi has the best post-win story. The day after the Oscars ceremony saw the studio's secretaries answer calls by referring to it as "M-Gigi-M." Too bad the rest of the film is a bit of a slog, and a knock-off of sorts from another iconic musical. It is easy to refer to Gigi as "My Fair Lady Jr." not only because Leslie Caron filled in for Audrey Hepburn (who performed the role on stage), but because the story in some ways has the same literal structure and conspicuous song cues ("Gigi" is basically "I've Grown Accustomed to Your Face"). Add in that it features plenty of older men's affection for younger girls to the point that there's a creepy song called "Thank Heaven for Little Girls," and you get one of the most unfortunately dated musicals to ever win Best Picture. If only the songs were a little more memorable.