26. Loverboy (1989)
Not to be confused with the way-not-sexy Kevin Bacon-directed Kyra Sedgwick drama about single mothers, this superbly '80s-racist comedy stars a pre-Grey's Anatomy Patrick Dempsey as a college dropout pizza delivery boy who happily delivers breadsticks on the side. And by "breadsticks" we mean "gigolo cock."
Among the unhappy married women Dempsey services: Kirstie Alley, Charlie's Angel Kate Jackson, and Carrie Fisher. The moral of the story is that life as a prostitute is 100 percent fulfilling and educational. Just like in real life.