Touch of Evil (1958)

Despite this flick being an Orson Welles piece, American audiences weren't so touched by the storyline. Oddly enough, it did numbers in Europe which, eventually, turned into American approval. It's highly regarded as one of films greatest film noirs. 

Some Like It Hot  (1959)

Marilyn Monroe excels in this screwball film alongside Jack Lemmon and Tony Curtis. Monroe does a bunch of wonderful musical numbers that are career-defining. The plot of this film is also intriguing and eye-catching for the time period: two men witness a mob hit and end up joining an all-female band disguised as two women to keep their identity safe.