5. Harold and Maude (1971)
Director: Hal Ashby
Stars: Ruth Gordon, Bud Cort
According to Harold and Maude, the best way to come into adulthood is to form a romantic relationship with a real adult. That is, a 79-year-old woman. Harold (Bud Cort) is the classic 20-year-old: he's depressed, he constantly fakes suicide to try to draw the attention of his distached mother, and he's entirely disillusioned by life. Then, he meets his own version of a manic pixie dream girl, in the form of the lively old lady Maude (Ruth Gordon).
The dark comedy of the unlikely romance may seem kind of, well, gross, but while viewing Gordon's Maude, it's completely believable that someone would fall for the energetic and charming elder and would be better for it, finding joy in everyday life. —TA