It's Always Fair Weather (1955)
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Bittersweet movie with fantastic songs and dance sequences
Gene Kelly does what he does best in It's Always Fair Weather, which is find ways to show off. The dance numbers are difficult - tying something to his feet, impossibly synchronized with dancers shot separately, roller skates - and he and his cast pull it off like the athletes they are. Cyd Charisse is abominably underused however, getting one dance number, and not even with Kelly himself. But then, while she's required for his character to "arc", this isn't her story. It's the tale of three army veterans who, in 1945, promise to be friends forever, and bet their barman they'll be back to prove it in 10 years. On the date, they find out they've grown apart and no longer recognize or like each other. Interestingly, they don't recognize or like THEMSELVES either, and through that realization, may be healed. It's a little more adult than the flighty dance numbers and television-of-the-era spoof might otherwise indicate. There are some definite lulls when we spend too much time away from the song and dance, but also some fun transition ideas to get us from point A to point B. In terms of old-fashioned musicals, you could do a lot worse.
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In 3 official lists
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This movie ranks #42 in 100 Musicals (BFI Screen Guide)
This movie ranks #457 in Doubling the Canon
This movie ranks #474 in TimeOut's 1000 Films to Change Your Life