For me, a absolutely vital film is Bill Moyers' interview with Myles Horton (founder of the Highlander Folk School) from about 1980 for the program Bill Moyers' Journal. It is called "Adventures of a radical hillbilly." I have used it countless times to underscore what it means to be a democratic leader and learner and what a really authentic process of empowerment looks like.
For issues of diversity and especially to shed light on white privilege, I have found that Lee Mun Wah's "Color of Fear" is superb. I especially appreciate the first half.