17. “Singin in the Rain”, Gene Kelly and Stanley Donen (1952)

Part of The 100 Greatest Movies I’ve Ever Seen list.

Singin in the Rain

Singin in the Rain

dir. Gene Kelly and Stanley Donen scr. Betty Comden and Adolph Green cin. Harold Rosson with Gene Kelly, Donald O’Connor, Debbie Reynolds, and Jean Hagen

In 100 words: The greatest musical ever is also one of the most perfect and most delightful exercises in pure, blissful entertainment. Its spoof of Hollywood is right on the money, but it’s a gentle poke, never mean-spirited and does it in a clever, hilarious way. Visually stunning, with fantastic pops of color and design, while its edits are sharp and perfectly timed. All actors are charming and deliriously good, with Kelly, O’Connor, and Reynolds delivering exacting and mind-blowing dance choreography and singing without seemingly breaking a sweat. Plus, Lina Lamont is perhaps the greatest comedy punchline ever. Excellent from start to finish.

Other Movies for Context: Among musicals, this is the peak of the form, the kind that gets everything right. I can only think of maybe three other musicals that was built to be this fun: Mary Poppins (1964), Top Hat (1935), and Hairspray (2007): All great fun, some might be darker, but overall tone is magnificent. Nothing though tops this.

52. “The Umbrellas of Cherbourg”, Jacques Demy (1964)

Part of The 100 Greatest Movies I’ve Ever Seen list.


The Umbrellas of Cherbourg aka Les Parapluies de Cherbourg

dir. Jacques Demy scr Jacques Demy cin. Jean Rabier with Catherine Deneuve, Nino Castelnuovo, Anne Vernon, and Marc Michel

In 100 words: Artifice gives way to a naked display of emotions in this magnificent musical that simultaneously pays homage to Hollywood as it comments on their phoniness. The novelty of having an entirely sung-through musical wears off immediately, but Demy thankfully has more up his sleeves than that: the tragic story of his young lovers is heightened by the sweep of Legrand’s gorgeous jazzy music and Demy’s colorful art design. The overwhelming vivacity of the colors and the music is just cover for the most devastating love story told onscreen that reaches its peak with its stunning coda. Prepare to weep uncontrollably.

Other Movies for Context: Jacques Demy continued his gorgeous partnership with Michel Legrand, the composer for the music here, with his similarly stylish (if more refined pop colors) The Young Girls of Rochefort (1967), starring Deneuve again. But obviously, the movie that feels closest to this is La La Land (2016), which has the same jazzy vibe, colorful design, and a similarly devastating love story at its center.

83. “A Star is Born”, George Cukor (1954)

Part of The 100 Greatest Movies I’ve Ever Seen list.

A Star is Born

dir. George Cukor (1954) scr. Moss Hart based on a story by William A. Wellman and Robert Carson cin. Sam Leavitt with Judy Garland and James Mason

In 100 words: An exuberant, joyous, but surprisingly moving experience, This remake features a shockingly honest treatment of topics that do not always spring to mind when one thinks of a musical: alcoholism, suicide, and emasculation. But Cukor’s exploration of a woman’s rise in Hollywood coinciding with her husband’s downfall is simultaneously sweeping and miniscule; a grand time and a rainy-day weepie at the same time. Songs are perfectly staged to maximize impact, while vivid colors and precise editing keep the experience engaging. All this topped by two of the 50s’ most incredible performances: Garland and Mason’s duet is one for the ages.

Other Movies for Context: Obviously, there are the two other A Star is Born films from the 30s and 70s, with Janet Gaynor and Barbra Streisand respectively in the Judy Garland role. But as far as musicals that were this dark? I think of New York, New York (1977) by Martin Scorsese, starring Garland’s daughter Liza and Meet Me in St. Louis, Vincent Minnelli’s movie musical starring Judy Garland.