Some Like It Hot, 1959 Though it's hard to say whether this film gave Monroe her best role, there's no doubt that this movie is the best one she ever starred in. The movie is effortlessly funny, and though Monroe's Sugar Kane is a silly blonde, her performance is sincere and sympathetic. Monroe almost has you believing that Sugar's next ill-advised love affair will work out for her (and her crooning of "I Wanna Be Loved by You" can't be missed). Image Source: Everett Collection