1. Singin’ in the Rain (1952)

Debbie Reynolds and Gene Kelly
Singin’ in the Rain being in the number one spot should be no surprise. I think it’s a film that should be required viewing for everyone. It contains great dialogue, physical comedy, dancing, music and also early Hollywood history. When one mentions Gene Kelly, Singin’ in the Rain immediately follows. Leonard Bernstein once said that after viewing the famous singing in the rain number that it was like “the reaffirmation of life.” And I think Bernstein is right. Of all the movies that try to capture that defining moment when one realizes they are falling in love, that iconic dance number does it effortlessly.
2. On the Town (1949)
Three sailors on leave in New York City for one day. There are a couple of things that put this movie at the number two spot. The first factor is the on-location shooting used in the opening sequence of the film. On the Town was the first musical to shoot on-location. Kelly had demanded that the opening song (“New York, New York”) be shot in New York City. This on-location shooting would have a huge influence on later musicals such as West Side Story. While Kelly had experimented with a dream sequence ballet in The Pirate, it’s in On the Town that we see a dream sequence ballet that would be later refined in An American in Paris and Singin’ in the Rain.
3. An American in Paris (1951)
While the plot is predictable and the chemistry between Leslie Caron and Kelly is awkward at various times, An American in Paris is a technicolor love letter (think Meet Me in St. Louis). The art direction and sets are beautiful and something movie goers will never see anything like again. And it’s the 17-minute ballet at the end of the film that makes this movie famous. Taking inspiration from French Impressionists, each set in the ballet sequence is based off a famous Impressionist painter (i.e. Utrillo, Van Gogh, Manet, etc.). The sets come to life as Kelly and Caron dance through them to the music of Gershwin’s “An American in Paris,” which lends the film title. If you need one reason to watch this film, its to see Kelly make an “on-screen art ballet” accessible to American audiences.
4. The Pirate (1948)

Gene Kelly and Judy Garland
Let me be the first to say that this musical might not be for everyone. First off, no one wants to see Kelly in a mustache (he even said that) and the plot is a little bit ridiculous. But if you can leave all that behind and focus on the great comedy of The Pirate, you are in for a fun and somewhat campy movie. Judy Garland is at her comedic best and has fantastic timing. It shows viewers that she could do awesome comedy, if given the chance. Gene Kelly hams it up by parodying early swashbuckler actors like Douglas Fairbanks and Errol Flynn. This is a cult musical with excellent dance numbers that is definitely worth watching.
5. Summer Stock (1950)
At first glance, Summer Stock might be another “lets put on a show!” musical, but this a bright musical with several fantastic dance numbers. This was to be Garland’s last movie at MGM. Her poor physical and mental health were now affecting her films. Kelly was reluctant to star in the film, due to just coming off from the highly successful On the Town. But Kelly did it for Garland. Kelly’s first film was with Garland in For Me and My Gal and she helped him get through his first movie. They would become great friends and co-stars. And it’s in Summer Stock that Kelly helps Garland through her last MGM musical. Containing some great dance scenes (i.e. Garland’s famous Get Happy number) and comedy from Eddie Bracken and Phil Silvers, Summer Stock is a simple but highly enjoyable musical that deserves attention.
