More movies like 'The Comedy'.

I can't think of any

somehow jarmusch's "Stranger Than Paradise" comes to mind... even though they're quite different, there is similar energy and atmosphere

some good recco's in this thread, thanks all

Surprised that no one's mentioned Lars von Trier's "The Idiots"! Von Trier's film manages to set up even more awkward scenarios than, say, a an all-out comic film like "Borat" - and I thought almost immediately during the first bit of "The Comedy" of Von Trier's style (as also in "The Kingdom" and "The Boss of All")...

Mikkel Nørgaard's film "Klown" (2010) is also close. And another decidedly obscene, awkward, kind of flagrant film is Makavejev's satire "Sweet Movie" (1974)--with the caveat that Makavejev's movie is off-the-hook, even more frank & provocative/disturbing than "The Comedy." (I'd also recommend his somewhat more mainstream film "Montenegro")

I'd recommend Todd Solondz's films. Happiness, Welcome to the Dollhouse, and Storytelling.

Eagle vs. Shark

There is a film called "Frenemy" aka "Little Fish Strange Pond" which reminds me of The Comedy for some reason.

http://www.imdb.com/title/tt1053880/

http://en.wikipedia.org/wiki/Little_Fish,_Strange_Pond

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Slacker, Withnail & I, Greenberg, and the original Lost Generation story, The Great Gatsby.