8. ‘Some Like It Hot' (1959)
Memorable quote: “Story of my life. I always get the fuzzy end of the lollipop.”
Laugh factor: Like “Tootsie,” this is a cross-dressing comedy. Unlike “Tootsie,” it features one Marilyn Monroe as a ukelele player. So the question becomes, how does a guy win Marilyn Monroe while dressed in drag? Tony Curtis and Jack Lemmon have a lot of fun trying to find out.