As you might expect from the no-nonsense title, this blistering 30s Warner Brothers thriller is about a man who escapes from a brutal southern chain gang. Things go better than you might expect for him after that, as he becomes a thriving businessman, only to end up right back in the chain gang due to the treachery of unscrupulous people in the establishment. Even though the movie is 80 years old, it still packs a huge punch.
"Cool Hand Luke"
60s and 70s: An iconoclast who refuses to play by society's rules. So of course he ends up in a Florida chain gang, and he makes a couple brief and exciting escapes, always ending up right back where he started. And since "prison escape movie" isn't exactly the most optimistic subgenre of movies, a happy ending isn't assured.
If you think southern chain gangs are tough, try a Turkish prison. That's what the main character of Alan Parker's based-on-a-true-story "Midnight Express" gets to do after he's caught trying to smuggle drugs out of the country. The conditions are beyond unbearable, and he's forced to fend for himself in a violent and brutal environment despite his American citizenship and moneyed parents doing everything they can to get him out. Eventually, he has to escape for himself, and this isn't the kind of prison escape you can make without hurting anyone. He gets his hands dirty, but he makes it out alive.
"Escape from New York"
Here's an even worse scenario than getting caught in a Turkish prison: You live in the far-flung future of 1997, and you're dropped into New York City, which has been converted to a giant prison colony. Your mission is to rescue the President of the United States, and if you don't do it in 24 hours, you die. Sounds like the prison escape movie to end all prison escape movies, right? And we haven't even told you about the land mines yet.
"Down By Law"
All these prison escape movies might make you think the genre is nothing but doom, gloom, and the occasional combination of both doom and gloom. But Jim Jarmusch is here to prove otherwise, with a delightful prison escape comedy starring Tom Waits, John Lurie, and Roberto Benigni. They meet in a Louisiana prison cell, and despite a pretty serious language barrier they all become friends and escape, roaming the countryside and arguing with each other. And Benigni keeps saying "I ham a good egg," which somehow never gets old.
"The Shawshank Redemption"
Another unimpeachable entry into the prison escape genre, "The Shawshank Redemption" makes prison seem almost nice enough not to want to escape from. But escape Tim Robbins and Morgan Freeman do anyway, after learning lots of valuable lessons about life. One of which is "get busy living, or get busy dying," and another is "people don't pay attention to your shoes." Good advice if you're planning a prison break.
"A Perfect World"
Clint Eastwood's follow-up to "Costner) on a chase across Texas with a young boy hostage in tow. All Kevin Costner wants is to make it to Mexico so he can spend the rest of his life in peace, but society just won't let him, man. At least they didn't make him go back to prison.