18. The Seven Year Itch (1955)
Director: Billy Wilder
Stars: Marilyn Monroe, Tom Ewell
Vacation destination: Manhattan
The Seven Year Itch is the oldest film on our list, but it's safe to say the classic film's appeal hasn't waned at all, thanks to the ever-nubile Marilyn Monroe.
Richard (Ewell) sends his wife and kids to Maine for vacation, but his intentions are less admirable and more selfish: He's the one who really wants to get away. Richard is smack in the middle of a sultry summer in New York City and experiences the titular itch (which refers to a man's desire to be unfaithful in his seventh year of marriage) when he meets Ms. Monroe in all of her full-bodied glory. But admittedly, if we saw Marilyn's dress billow up while standing over a subway grate, we might have a desire or two to scratch out ourselves.