We all need some lightheartedness right now. For me, one of my favorite things to do when I’m feeling down is pop on a fun movie. I’m a huge fan of classic movies and musicals, and they feel like such a nice escape when I’m feeling overly stressed or sad. Since I’ve tried to basically make this one of my personality traits since I was a teenager, I thought I’d run through some of my favorites that are available to stream. Buckle up, because I couldn’t narrow it down under 15.
Singin’ in the Rain
1952 - Rent on Amazon
This is for sure one of my favorite movies, and one of the first ones I turn to to cheer me up. It’s a musical about the difficult transition in Hollywood from silent films to “talkies” in the late 1920s. It stars Gene Kelly as silent film star Don Lockwood, Debbie Reynolds as young up-and-coming actress Kathy Selden, Donald O’Connor as Don’s best friend Cosmo Brown, and Jean Hagen as Lina Lamont, Don’s frequent costar. The problem with the transition is how to make Lina’s grating voice appeal to audiences, but Don, Kathy, and Cosmo have something up their sleeves. Highlights of the film include the famous “Singin in the Rain” sequence of course, the “Good Morning” sequence where Don, Kathy, and Cosmo stay up all night coming up with their plan, and the elaborate film plan Don & Cosmo come up with (this includes the dance sequence with Cyd Charisse in the green flapper dress you may have seen before). It’s such a heartwarming movie that I think it should be the first one you watch out of this list!
Funny Face
1957 - Watch with Amazon Prime
I’m a huge Audrey Hepburn fan, and this is one of my favorite films of hers. Funny Face is a musical about a fashion photographer (played by Fred Astaire) who discovers a book shop clerk (Audrey Hepburn) and makes her a model. It also stars Kay Thompson as the editor of the fashion magazine. Most of the film is set in Paris and includes music by George & Ira Gershwin. Highlights include the darkroom sequence, the photography montage in Paris, and Kay Thompson’s “Think Pink!” song at the beginning of the film.
Easter Parade
1948 - Rent on Amazon
Judy Garland and Fred Astaire star in this Irving Berlin musical about stage performer Don Hewes (Astaire) who finds a new partner in chorus girl Hannah Brown (Garland) after his old partner (Ann Miller) decides to do a solo act. At first Don tries to make Hannah into a clone of his old partner, but he finds their real strength as a team comes when he allows Hannah to be herself. This movie has some of my favorite musical numbers, from Fred Astaire’s “Drum Crazy,” to Ann Miller’s “Shakin’ the Blues Away,” to Judy Garland’s “Easter Parade” at the end.
Summer Stock
1950 - Rent on Amazon
This might be my favorite Judy Garland movie if I had to pick just one. She plays Jane Falbury, a woman running a small and ailing farm. Jane is in the middle of struggling to make ends meet when her sister (Gloria DeHaven) brings her boyfriend (Gene Kelly) and his theater troupe to the farm to put on their show. Jane is against it at first, but decides to let the group perform there as long as they pitch in, and she soon feels the pull of the theater. Judy Garland’s famous “Get Happy” number is from this movie, and Gene Kelly also has a stunning dance routine where he’s inspired by the sound of a squeaky floorboard and a newspaper.
High Society
1956 - Rent on Amazon
This is a musical version of The Philadelphia Story, where Grace Kelly plays Tracy Lord, an heiress who must choose between three suitors: her jazz musician ex-husband (Bing Crosby), her boring businessman fiance, and an undercover tabloid reporter who falls for her (Frank Sinatra). Highlights include Frank Sinatra and Celeste Holm (playing a tabloid photographer) singing “Who Wants to Be a Millionaire?” and Sinatra & Crosby’s rendition of “Well, Did You Evah?”
Meet Me in St. Louis
1944 - Rent on Amazon
This is another of my favorite Judy Garland films. Meet Me in St. Louis shows a year in the life of the Smith family, starting in the summer of 1903 and leading up to the World’s Fair in St. Louis in the spring of 1904. This is one of the most feel-good movies I’ve probably ever seen, and for me it almost rivals It’s a Wonderful Life in that aspect. Judy Garland is at the top of her game here - she looks absolutely beautiful and her voice is more stunning than ever. The highlights of the film for me are “The Trolley Song,” and when she sings “Have Yourself a Merry Little Christmas” towards the end.
Charade
1963 - Watch on Amazon Prime
This is one of the few non-musicals on this list. This mystery/thriller stars Audrey Hepburn and Cary Grant and starts with the death of Audrey Hepburn’s husband. As it turns out, he was in a group that took part in a huge robbery, and the rest of his gang scheme to get the money out of her and also plot to make sure they’re the sole inheritor. There are so many twists and turns in this movie, and it’s again set in Paris. My favorite part is when Cary Grant showers with his suit on.
Two for the Road
1967 - Rent on Amazon
This is the other non-musical and maybe my favorite Audrey Hepburn movie. It stars Hepburn and Albert Finney as husband and wife, and a non-linear timeline shows the course of their first meeting and their lives together. It shows an honest and sometimes not pretty portrayal of marriage, with infidelity and fights as well as love and happiness. It also stars a young William Daniels (aka Mr. Feeny from Boy Meets World) as a friend of the couple.
Gentlemen Prefer Blondes
1953 - Rent on Amazon
This film is too iconic to not include in this list. Marilyn Monroe & Jane Russell play best friends Lorelei Lee and Dorothy Shaw who are traveling by boat to Paris. Lorelei’s suspicious future father-in-law has hired a private detective to spy on her to make sure she “behaves” on the boat, and Dorothy befriends him, not knowing his true identity. Lorelei catches the eye of an older, rich man, as well as many others, and Dorothy tries to keep her in line. Marilyn Monroe’s famous “Diamonds are a Girl’s Best Friend” number is from this movie, and my other favorite part is Jane Russell singing “Ain’t There Anyone Here for Love?” to the entire Mens’ Olympic Team on the boat with them.
Some Like It Hot
1959 - Watch on Amazon Prime
This is another great Marilyn Monroe film. Two musicians (Tony Curtis & Jack Lemmon) witness a mob hit and then have to go on the run. They join an all-girl band and dress in drag to blend in. Tony Curtis falls for the singer in the band, played by Marilyn Monroe, while Jack Lemmon’s alter ego Daphne is the object of an older man’s affections. Many complications ensue. There are a few songs in the movie, but I wouldn’t necessarily call it a musical - every song is performed by the band, instead of the usual musical formula of people randomly bursting into song.
The Sound of Music
1965 - Rent on Amazon
Whenever I was homesick in college, I would watch this movie, and it always cheered me up. Julie Andrews plays Maria, a nun sent to become a governess to the von Trapp family, made up of a strict, widowed father (Christopher Plummer) and his seven children. Maria brings light and music into their lives and changes them all for the better. This is set in pre-World War II Austria as tensions with Germany begin running high.
On The Town
1949 - Rent on Amazon
This fun musical centers on three sailors (Gene Kelly, Frank Sinatra, and Jules Munshin) on shore leave for 24 hours in New York City. They try to find fun and romance before their time in the city is up. It also stars Vera-Ellen as “Miss Turnstiles,” Betty Garrett as a sassy taxi driver, and Ann Miller as an anthropologist they meet in the Museum of Natural History. The best part is the “Miss Turnstiles Ballet” where Vera Ellen performs quick dance routines around each personality trait Gene Kelly lists while describing her.
The Band Wagon
1953 - Rent on Amazon
I’ll admit I haven’t watched this movie in a very long time, but I do remember loving it. Fred Astaire stars as washed-up star Tony Hunter who agrees to be a part of his friends’ (Nanette Fabray & Oscar Levant) Broadway show to give his career a kick. But they hire pretentious “artistic” director Jeffrey Cordova (Jack Buchanan) who changes the show beyond recognition, including hiring prima ballerina Gabrielle Gerard (Cyd Charisse) to star alongside Tony, and it’s hate at first sight. They still strive to work together to put the show on. Highlights include the Central Park dance sequence with Cyd Charisse & Fred Astaire as well as their “Girl Hunt Ballet.”
The Harvey Girls
1946 - Rent on Amazon
This is a lesser-known Judy Garland movie, but still one of my favorites! She plays Susan Bradley, a woman traveling West on the train to marry a penpal. She meets a bunch of friendly girls going to work at the “Harvey House,” and when her plans with her penpal don’t work out, she joins them. I love this movie because it not only has a romance storyline, but also shows the importance of female friendship. Angela Lansbury also stars as a saloon dancer competing with Judy Garland for the saloon owner’s affections.
An American in Paris
1951 - Rent on Amazon
If you’re a Gene Kelly fan, you must watch this in addition to Singin’ in the Rain. He plays Jerry Mulligan, a struggling artist living in Paris with his friend, a would-be concert pianist (Oscar Levant). Jerry falls for Lise (Leslie Caron), a young French woman already engaged to a cabaret singer. This film has some of the most stunning dance numbers I’ve ever seen, from Leslie Caron dancing to different personality descriptions ready by Gene Kelly with monochromatic backdrops (similar to On the Town) to the final incredible 20-minute ballet sequence.
If you’re still reading, thank you! I also would have added White Christmas to this list because it’s my all-time favorite movie, but it’s not available to stream anywhere right now. If you can find it, I recommend that too - it’s not just for Christmas. Let me know if you watch any of these, and if you like them!