One of the best indy films to come around in a long while is the terrific little film The Jimmy Show, written by Frank Whaley. This is about a loser guy who wants to be a stand up comedian but has no talent. He's blown all his opportunities, made poor choices, and is pretty much an unlikeable tool. Though this is by far one of the best screenplays I've encountered as of recent.
Although Dan in his review compares it to The King of Comedy, and notes that it's not quite a great film, but close, I have to argue that the screenplay is great. It is a perfect depiction of not only working class life, but the idle life of a "dreamer" who cannot accept his realities. And there is also a great performance by Ethan Hawke in it, as his pal.
The reason this film was not well received, I have to believe, is due to it's "depressing nature," where viewers might have gone into it thinking it's a comedy. It's actually quite a sad film, and is the closest thing to a Richard Yates novel I've ever encountered. Yates is known for distilling those important scenes in books down to their essence, and many of the characters are not only "losers" but believable losers, and also understated.
Too much in Hollywood and also the publishing industry focuses on hyperbole, rather than those small moments in life that everyone witnesses. What they don't realize is that by focusing on those smaller subtleties in life, you are forced to pay closer attention not only in the art, but in real life as well. The reason Jimmy O'Brien is such a well sketched character is because you've met people like this before.
The Jimmy Show distills these moments nicely, giving a believable and pathetic (in the best sense of true pathos) character. Visit the trailer here--and read Dan's review. Or wait to read it if you don't want spoilers. Then give the movie a shot. I can't recommend it enough.