Just of the top of my head, not comprehensive by any means...
Brief Interviews with Hideous Men (2009)
John Krasinski's directorial debut, based on a David Foster Wallace story. A movie by actors, for actors. Really just a series of amazing monologues.
Little Children (2006)
Kate Winslet & Patrick Wilson are stay at home parents having an affair. This was my introduction to Jackie Earle Haley, who plays a sex offender. It brings up a lot of great questions.
Lake of Fire (2006)
Probably not for everyone. A very in-depth and graphic documentary about abortion. I believe it's ultimately pro-choice, but it examines both sides of the debate.
The Last Kiss (2006)
Seriously, Zach Braff gives one of my all time favorite performances.
The Sacrament (2013)
A horror movie based loosely on the Jonestown massacre. Gets under your skin and will creep you out for days.
Tim's Vermeer (2013)
Super fascinating documentary by Penn Jilette of all people. Maybe you guys watched it when I wasn't on the boards, but I have never met another person who's seen it. It's about a man who methodically figures out how a Dutch painter created his masterpieces.