Crumb is probably the ultimate for me, but here's some obscure ones:
Floundering, Gen-X indie that is hard to categorize and has loads of famous or soon-to-be-famous actors in cameo roles. Some would relate to the character's internal monologues. Hated the shiny-happy ending though.
God's Lonely Man, extremely bleak Taxi Driver redux with a performance by the lead that almost reminds me as much of Woody Allen as it does Deniro. Good DVD commentary too.
Even Hitler Had a Girlfriend, which I've mentioned elsewhere, but it's a mini-masterpiece. A sex-obsessed security guard spends his entire life-savings on escorts. While it's a goofy low-budget comedy packed with gratuitous T&A, it doubles as a superior character study of a desperately lonely, overweight, charismaless, involuntary celibate.
The Jimmy Show, stars one of my favorite actors Frank Whaley as a born loser/failure who tries a shot at stand-up comedy on local open-mike nights. Ultra-depresso and the stand-up segments are painful. The movie is almost like a realistic continuation of Whaley's earlier loser role in
Career Opportunities if his character's adventures with Jennifer Connelly were just an extended dream he had sleeping at work, leading to him waking up to another lost job.
Does anyone know if
Roman is any good? I hear it's like
May with a male character, but then again I haven't seen
May yet either...