One film that I can watch over and over (if only for Tom Waits and the hilarious Roberto Benigni) is Down By Law.
Released in 1986 by Jim Jarmusch (who also directed Dead Man, featuring Johnny Depp, Broken Flowers and various other amazing films. He also has impressive hair.), Down By Law sees three questionable gentlemen thrown into a cell together. I will say no more of the storyline, however, as with most of Jarmusch's films, the humour is witty yet dry, and will have you quoting lines for days after.
The film itself holds special memories for me, as it was one of the first films my boyfriend introduced me to, and also to the music of Tom Waits and the joyful insanity of Roberto Benigni.
I highly suggest seeking out this film, and any other Jarmusch work!