Benny & Joon (1993) Benny & Joon is a romantic comedy that seems like it shouldn't work, based on the unconventional premise alone. Mary Stuart Masterson plays the titular Joon, who is supported by her protective brother Benny (Aidan Quinn) and suffers from an undisclosed mental illness that is most likely schizophrenia. In exchange for losing a hand in poker, she's forced to give an opponent's relative, the eccentric Sam, played by Johnny Depp, a place to stay for a few days.
Blow (2001) When choosing to portray characters adapted from true stories, Depp tends to lean toward the subversive, and his character in Blow certainly keeps with the trend. Like Donnie Brasco, Blow takes place in the '70s, but this time Depp's character, George Jung, is firmly camped out on the wrong side of the law. Depp gives a fascinating portrayal as "Boston George".