Director: Tom DiCillo
Year Released: 1991
Struggling singer Johnny (Brad Pitt) can't seem to get his musical career going or get enough money to see him through, and he goes from one bad relationship with Darlette (Alison Moir) - who's simultaneously dating another man - to living with Yvonne (Catherine Keener), who he cheats on. It's an oddball comedy without the timing, and a rambling, disjointed "indie" saved solely by its (still famous) cast: Pitt's goofus is a dimwit but charming, and then there's Nick Cave in there singing ("They call me Momma's Boy / But I don't care") and Samuel L. Jackson on bass (of course Keener isn't too bad either). When it comes to deadpan humor with puffed up hair and pointy shoes, the Leningrad Cowboys did America better.