My friend Andrew Takeuchi went to jail with Morgan Spurlock for 30 days this spring and the evidence is now a free download on iTunes.
Spurlock has a TV show called 30 Days; Andrew was the Director of Photography for the 30 days that Spurlock spent in jail, which will be the season's grand finale. Although Andrew got to go home most nights, he was there in the jail with the camera the whole time. iTunes has a "making of" download where Andrew gets to be in front of the camera, too -- it also includes lots of the jail footage he shot.
Bonus: In an interview about the show, Morgan Spurlock calls David Letterman a "strapping lad."