5 Magneto, X-Men 2: X-Men United (2003)
In X-Men 2, Mutant terrorist Magneto (Ian McKellen) is being kept in a prison made completely of extra durable plastic, lest he use his vast magnetic powers to escape. His ingenious solution? Have his shape-shifting right hand woman Mystique seduce a guard at his favorite bar, then inject his bloodstream with iron ore, which Magneto mercilessly extracts the very next time said guard is on duty. With a good amount of metal to play with, the plastic prison and its staff become short work.
4 Hannibal Lecter, Silence of the Lambs (1990)
The bloodiest escape on our list, but then again hyperintelligent psychopath Dr. Lecter does tend to savor most things, especially murder. After having his way with two guards dumb enough to enter his cell unarmed in order to serve him his second dinner, Lecter calmly resumes enjoyment of a classical music selection, before wearing one of the dead guards’ face and uniform as he is whisked away in an ambulance as the dead man. Never has jailbreaking and extreme mutilation been handled with such leisure and refinement as it did in Silence of the Lambs.
3 James Allen, I Am a Fugitive From a Chain Gang (1932)
Returning WWI vet James Allen takes to the road and is soon sent to a Southern chain gang for a crime he didn’t commit, where he spends hellish months before escaping and starting a new life with a prosperous career in Chicago. He is eventually betrayed by his treacherous wife, and tricked by state authorities with the promise of a pardon into returning down South to serve out the rest of his initial sentence. He makes his perilous second escape, (complete with dynamite) transforming into the wily criminal he never was to begin with.
2 The Joker, The Dark Knight (2008)
After willfully getting himself caught by the Gotham Police Department’s Major Crimes Unit and being subjected to a thorough interrogation/beating at the hands of the Batman, the Joker sends Bats and Jim Gordon on a race through Gotham to prevent some serious district attorney splatter from happening, and is left to implement a dastardly bust-out, with the aid of an ever-trusty fat guy bomb. The fleeing clown prince celebrates by hanging out the car window and reveling in the night sky like the mangy dog he is.
1 Andy Dufresne, The Shawshank Redemption (1994)
Come on, you’re not surprised. What possibly beats this? After a lengthy, wrongful imprisonment in Shawshank Prison, crafty banker Andy enacts a long gestating escape plot much to the chagrin of the uberdick warden under whom he toiled as an expert money launderer. After traversing a route most fecal, Andy is free in the pouring, purifying rain. Talk about cathartic.