Many people tend to underestimate young people's capacities for thinking about weightier topics that affect their lives. I have always believed that documentaries can be a great way to get them engaged in larger issues, but the documentaries have to be sufficiently entertaining.
Following is an assortment from the last 10 years that I feel do both: they are interesting and can help young people view the world with a more sophisticated outlook. Maybe mix one of these into your movie night list, and share your own recommendations in the comments!
This is my personal favorite on this list, and great viewing even if you don't have kids in your life. Follow elementary students as they train for a ballroom dance program developed in the New York City Public School system.
Girls Rock! - 2007
Follows girls and young women at Rock 'n' Roll Camp as they try to break free of the conformity expected of them at home. Watch them become self-possessed badass rocker chicks!
Film site [girlsrockmovie.com]
Bowling For Columbine - 2002
I like this movie because it's a great jumping-off point for discussing media manipulation and propaganda, even more so than for discussing gun violence.
Film site [bowlingforcolumbine.com]
Frontline: The Merchants of Cool - 2001
Speaking of media manipulation, Boing Boing contributor Douglas Rushkoff put together this classic must-see coverage of how young people are manipulated as consumers. As someone who has been paid to sell stuff to the "tween" and "yurban" markets, I can attest to much of what's covered here.
Program site [pbs.org]
Spellbound - 2002
The charming classic about finalists at the 1999 National US Spelling Bee.
American Teen - 2008
This film follows a group of high school seniors in my home state of Indiana, but it could be just about anywhere in small-town America.
Film site [americanteenthemovie.com]
Louder Than A Bomb - 2010
This film is making the festival rounds right now. What I like about this look at the Chicago poetry slam scene is that there's a real range of experiences among the young people depicted. Taking young people to a local film festival is always a great idea, too, so see if you can find this!
Film site [siskeljacobs.com]