Just watched "The Wackness". Could be that I'm the same age as the protagonist and it's set in 1994, but I thought it was well done. Ben Kinsley is excellent as usual and the lead did a credible job. Plus, fantastic soundtrack (Biggie, Tribe, etc).
Also, I can't recommend Young @ Heart more highly. Most pics in the "uplifting documentary" category are way too treacle-y, but this was just right. The filmmaker is a shit interviewer, though.