2. Singin' In The Rain - Singin' In the Rain (1952)
Widely considered the greatest musical of all time, 1952's Singin' in the Rain depicts Don Lockwood, played and danced impeccably by Gene Kelly. Don is a silent movie superstar, the equivalent of a modern day Brad Pitt. His Angelina Jolie, Lina Lamont, is another silent film star with a voice slightly more annoying than Fran Drescher. Don, attempting to flee from his violently adoring fans, happens upon the adorable Kathy Selden. Though Kathy initially insults Don and his method of acting, he finds himself smitten with her. He finally tracks her down, they share a dance, and she's his. As the movie progresses and Don's love for Kathy grows, he drops her off at her house and steps out into the rain. He's so happy that he can't help but sing and dance, twirling his umbrella around. According to the Hollywood legend, Kelly pulled off this scene in which he splashed around in puddles with a 103 degree fever, a surefire way to get a crippling bout of pneumonia.