I really like the Morgan Spurlock created show 30 Days. If you’re not familiar, Morgan Spurlock is the guy who made Super Size Me, and he’s extended that type of stunt documentary to create the series. People spend 30 days in someone else’s shoes to better understand other’s lives or the other side of a polarizing issue The first season included Spurlock and his fiance spent 30 days living on minimum wage, a christian living with a muslim family, and a homophobic man living with a gay man. This season has had an atheist living with a mega-church-attending christian family, an anti-immigration minuteman living with a family of illegal immigrants, and the finale will have Spurlock going to jail for 30 days.
The iTunes music store has both seasons of the show avaiable for sale. The powerful illegal-immigration episode and a making-of the jail episode are available for free.