Man on Radio in Red Shows -Garrison Keillor can make just about anything sound interesting in a relaxing sort of way. Offers a good look at all that goes into making Prairie Home Companion and of course praises the under appreciated far North. A lot of focus on average, real people. Recommend watching this on a rainy, contemplative day when you're a little more open-minded than usual.
Exit Through the Gift Shop -A Banksy documentary on the guy who sought to document Banksy. I think anyone can appreciate this one regardless of their knowledge of art, politics, Banksy, etc. At the bare minimum, it's fun to watch graffiti come alive. Ultimately, it offers an interesting commentary on art, street art, consumerism, etc. Recommend watching this with a mixed group.
180 º South -The protagonist travels down to Patagonia to meet up with the founders of both North Face and Patagonia. Several points of view and themes to this one. Largely a political message but travel/self discovery is prominent as well. Phenomenal landscape shots alone make this worth watching. Recommend watching this one late at night with a travel buddy/wife.