5. 'Singin' in the Rain' (1952)
Starring Gene Kelly and Debbie Reynolds in their most iconic roles, Singin' in the Rain took a lighthearted look at the transition from silent films to "talkies" and the Hollywood players who are part of it. It's the type of whimsical, classic musical comedy La La Land pays homage to. The film was later adapted into a stage show in 1985.