37. Harold And Maude (1971)
The romantic comedy has always tended to be one of Hollywood’s fluffier and less demanding genres, but that isn’t the case when it comes to the pitch-black classic Harold and Maude.
A suicide-obsessed 20-something strikes up a romance with an 80 year-old wild child at a funeral, and together they explore the meaning of life from their vastly different perspectives.
Hal Ashby’s cult classic was a flop at the time it was released, but over the last half a century Harold and Maude is held up as a true cult favorite, and one of the most unusual rom-coms ever made.