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Slide 6 of 8

Bus Stop, 1956

This film version of the William Inge play just might showcase Monroe's best work. In the movie, she plays cafe singer Cherie, who dreams of travelling to Hollywood and becoming famous. Monroe is a more confident and commanding presence in this movie than she is in past roles, and that's probably because she was calling more shots than ever. The star was very involved in the production of the movie, helping to design her own costumes and makeup.

Image Source: Everett Collection