Hi All,
Awesome list you've got going!
Salesman -- Recently re-released documentary by the Maysles Bros (Gimme Shelter, Grey Gardens) about door-to-door Bible salesmen. So awesome and analogous to poker. The dialogue could've been written by David Mamet (and remember it's a documentary).
Living In Oblivion -- Not super-obscure, but hilarious indie film about making indie films, starring Steve Buscemi and Catherine Keener.
She's So Lovely --Very dark comedy from the son of John Cassevettes. GREAT cast, and Sean Penn's best performance, IMO.
The Indian Runner -- Only meant to post 3, but mentioning Sean Penn reminded me of this gem, which he directed. Viggo Mortensen, Patricia Arquette, Charles Bronson showing some acting chops in a cameo.