In my review of School for Scoundrels, I complained about the way Arrested Development stars are chronically underused in big-studio films. Let's Go To Prison, at least, uses Will "Gob" Arnett as a major character, and he gives another great comic performance as a rich, spoiled brat stuck in jail. Too bad about the rest of the movie.
Dax Shepard, the poor man's Owen Wilson (even more than Luke Wilson, I mean) plays a petty thief repeatedly sent to jail by a crusty, no-nonsense judge. (Sheppard tells us, "If I had a nickel for every time I've been incarcerated, I'd have 15 cents.") The judge dies a few days before he can get his revenge, so he has to settle for framing the judge's son, getting him sent to the toughest prison in Illinois, and becoming his cellmate.
Let's Go To Prison was directed by Bob Odenkirk, from the wonderful Mr. Show With Bob and David, and the overall tone of his film can be described as strange at best. Amazingly, it's based on a non-fiction book about the American prison system, You Are Going to Prison by Jim Hogshire, and Sheppard occasionally recites some sobering facts and figures about how many Americans are locked up, but the filmmakers lurch uneasily between raising serious issues about the justice system, and going for cheap laughs.
I love a cheap laugh as much as the next guy, but most of the running gags in Let's Go To Prison are distasteful without being funny. In particular, there's the inevitable subplot about prison sex, with Shepard "selling" Arnett to a large, black, gay inmate (played by Chi McBride, from Boston Public, in a humiliating role) and faux-soul music playing whenever he tries to seduce him. In theory, this could be made funny, but not in Let's Go To Prison.
It's strange, how so many talented people – Odenkirk, Arnett, McBride, David Koechner (the sports guy from Anchorman) – can produce something as unfunny as Let's Go To Prison. I'm sure they'll all go on to do much better work in the future, and when they do, their involvement in Let's Go To Prison probably won't be featured prominently in the publicity materials.