Pi(1998), directed by Darren Aronofsky, would be my pick. I hated the movie in my first watch but that was the time when my watchlist was rather slim and I wasn't wise enough to truly grasp the subject matter. After many years of movies experience I gave it a rewatch and I was truly amazed how with such a low budget Aronofsky was able to give an intense, bizarre and somewhat horrifying experience to moviegoers .
[SPOILERS AHEAD]
The special thing about the movie is really it's bizarreness. A genius' quest to find a pattern in "pi" and hence unlock a code to Wall Street that begins to transform into an adventure that could answer the biggest questions of Human Existence and GOD plus atypical cinematography that revolves around a man sickened of genius are truly the spirit of the movie.
looks like most people are choosing movies, I have not watched any indie movie that I know of (that I know that it is indie), My favorite obscure indie title would be a video game called Stories the path of destinies. it is a good game and I am currently replaying it to make a review on it. It would be a pleasure if you check it out.
Never heard of it, sounds interesting though. I'll give it a go after reading your review on it. Be sure to post the link in reply. Thank you.
anyway the film really sounds interesting.