There are a lot of great jailbreak movies, which makes sense if you think about it. A prison is a naturally high stakes environment to set a story in; there's an intrinsic emotional appeal to the idea of an innocent man regaining his freedom; and because you can spin the prison as a corrupt tool of the man or as a place that punishes the legitimately guilty, you can populate your story with as many heroes, villains or anitheroes as you want.
Escape Plan is not a great jailbreak movie. Yes, it has high stakes - it's prison is supposedly the most secure prison ever made. Yes, it has an innocent man who needs to be freed at it's center. And yes, it has an appropriate number of heroes and villains in it. But what it doesn't have is common sense about it's context, and that proves to be the movie's undoing.
Before 9/11 saying that a prison housed "the worst of the worst" would cause the audience to imagine any number of threatening archetypes, but saying that in a post 9/11 movie is only going to conjure up terrorists... Especially if right after you say that you explicitly state that this prison has a population drawn from around the globe and you pointedly show Muslims praying. Make no mistake about it, this film is very aware of the war on terror: every time the two main prisoners (played by Sylvester Stallone and Arnold Schwarzenegger) anger the warden he punishes them with the sort of intense tactics that Guantanamo Bay was known for, like locking them into isolated sweatboxes where one entire wall is made up of flood lights they can't turn off. Bringing up the specter of Guantanamo Bay is an unspeakable mistake for this movie because it brings a heaviness to the proceedings that it isn't prepared to handle.
If you're like me and are totally repulsed by anything that's associated with institutionalized torture then this film will gross you out; it evokes barbaric acts and then backs off on how serious they were, which saddened me and then enraged me. But even if you aren't as repulsed by the idea of torture as I am, I still don't see why you would find this movie to be fun, because why would you root for someone to prove that it's possible to escape out of that prison? And in either camp you're going to have to deal with the fact that this story is completely unrealistic - if the warden is going to be vicious enough to torture his charges he isn't going to be dumb enough to let them continue to eat together at mealtime even after it's clear that they're planning something.
The main thing that makes jailbreak movies work, I think, is that they have a sort of mystique to them. There's an element of Houdini to them - escaping the impossible, flouting the man. But by evoking things that are disturbing instead of things that are magical Escape Plan shuts itself off from that type of mystique. Instead of thinking about how impossible it is to break out of the prison, I was thinking about how unpleasant Guantanamo Bay is, and instead of thinking about how bad-ass it would be to flout the man I'm thinking about how truly bad the man can be when he sets his mind to it. This movie is meant to be an entertaining diversion, but it's an unsavory reminder of the things that I would be happier if I could forget.
Winner: The Cat