I recently watched the documentary film '24 Hours on Craigslist' in San Francisco and I really enjoyed it. The film does a great job of tying together the nearly impossible: a random day of posts on Craigslist. This documentary is worth watching purely for the characters interviewed by the film. They are at times hilariously funny (some intentionally so) and provide a voyeuristic glimpse into who it is that drives the site's populist appeal: us.
I doubt my 70 year old dad, who uses craigslist regularly, would relate to or understand most of the folks in the film. But that's not really the point. '24 Hours on Craigslist' it makes you question who uses the site if we only saw 88 stories? What were the other 99.5% of people posting on Craigslist like and how much stranger could they be?
I will say that the rapid edits and amateurish shooting styles (different camera operators) make this indie documentary a little hard to watch at times but I definitely recommend this film.