1. Magnolia (1999):
Before The Master there was Magnolia. Director Paul Thomas Anderson's critically acclaimed follow up to the surprise 1998 hit Boogie Nights, featured a large ensemble, and more drama than Emily Bronte herself could have created. This rather abstruse film worked in ways that it simply should not have. There is little reason that Magnolia should have been nearly the success it was, not due to any fault of the movie but simply due to how involved and bizarre the premise was at the core of the film. However a brilliantly directed movie and a star cast which would put Ocean's 11 to shame, keep this movie from falling into a transcendental soup of nothingness. Little is explained and less is revealed so it's perfectly okay to fill in the gaps as well as you can. This is a perfect movie to watch and enjoy on your own and then occasionally name drop into casual conversation to show your superiority over friends and colleagues, if they ask you to explain the plot deftly change the conversation.
2. Mulholland Drive (2001):
I know David Lynch, you know David Lynch, so I shouldn't have to explain this movie to anyone let alone why it's great (hint it's the only time a Lynch has been a good thing). From Eraserhead to Inland Empire, David Lynch has been one of America's greatest cult directors since 1977 and shows no sign of losing his relevancy in the film-making world.
Originally conceived as a television show, Mulholland Drive feels like it's partially a pilot and partially a fully formed motion picture. This murky middle ground Mulholland Drive lives in is what makes the movie a classic ... and what makes it confusing as hell. There doesn't seem to be a beginning or an end to the film, it appears to be a convoluted Mobius Strip to the viewer. Although star Justin Theroux (Tom Haverford's fashion idol on Parks & Recreation) has stated, "I think he's genuinely happy for it to mean anything you want. He loves it when people come up with really bizarre interpretations. David works from his subconscious." I prefer to believe that David Lynch has a clear view of how his film ends and simply enjoys watching we simple mortals struggle towards trying to comprehend the meaning behind this film. While we attempt to decipher the undecipherable perhaps Lynch may be kind enough to make more Twin Peaks ... just as a personal favor, I'll make it up to him somehow.
3. Eternal Sunshine of the Spotless Mind (2004):
Eternal Sunshine of the Spotless Mind plays on a feeling we've probably all had, the idea of simply erasing unwanted memories, and turns that feeling into a brilliant and cute romantic science-fiction comedy. The film opens on Jim Carrey, an uptight emotionally withdrawn man (well in this film at least) meets Kate Winslet on a train, a free spirit, and despite their wildly different personalities they strike up a relationship...without either of them realising that they had done it before. The central plot device of this film is the idea of being able to remove painful memories from your past and never have to remember them again. Eternal Sunshine of the Spotless Mind is cyclical and one can watch the film over and over again. Smart and funny, Eternal Sunshine of the Spotless Mind is one of my personal favorite films, as well as having won an Oscar for Best Original Screenplay. It explores themes of forgiveness, love, regret and rebirth, and it also has David Cross which is always a treat ... always.
5. "Time To Dance" (2012):
I don't actually know if this short film constitutes an art-house film, but it's so damn awesome it deserves a mention even if it doesn't fully meet the criteria. In what is "technically" a music video for the French indie band The Shoes, Jake Gyllenhaal plays a serial killer that hunts down hipsters. The simple premise of the short is what makes it so brilliant, not a single word of dialogue was spoken and the gore is on par with an episode of Sons of Anarchy. With a runtime of a little over eight minutes, it's well worth the watch, and strangely hilarious. The other benefit of watching "Time to Dance" is that you will no longer need any advice on Hipster music because you'll finally be caught up to them.
P.S. If you decide to become a connoisseur of art-house films try to remember that despite how dutch they sound, Gus van Sant and Lars von Trier are not the same person, despite the fact that they pretty much do the same thing.