Marilyn Monroe's 5 greatest movies of all-time Gentleman Prefer Blondes (1953) — Monroe co-starred alongside Jane Russell in one of her biggest roles. This one sees Monroe perfecting her “dumb blonde” character and is considered to be her most crowning achievement. Niagara (1953) — The sexy 1953 thriller Niagara was one of Monroe’s first starring features and it centers on the dangerous risky appetites of a woman who schemes with her lover to murder her much older, violent husband (played by Joseph Cotton.) The Misfits (1961) — This drama was written for Monroe by her then-husband Arthur Miller, and sees her acting alongside her childhood hero, Clark Gable, as well as the great Montgomery Clift, Eli Wallach, and Thelma Ritter. Bus Stop (1956) — Bus Stop was Marilyn’s first starring role in a dramatic film and her first movie made after studying at the Actor’s Studio in New York. Some Like It Hot (1959) — Some Like It Hot is considered by many to be both Monroe’s best performance and her greatest film. The movie was ranked number one on the American Film Institute’s list of the funniest films of all time.