The character of Charles Westmorland/D.B. Cooper is based on an actual person (D.B. Cooper) who, in 1971, after hijacking an airliner, extorted $200,000 from its owner, Northwest Orient, and leaped off the airborne plane with 21 pounds of $20 bills strapped to his body. He was never found. The theory is that he was killed because his parachute didn't deploy.
Thirteen prisons banned this show.
Wentworth Miller was a last minute casting choice. He started filming about a week after auditioning/being cast.
Stacy Keach (the Prison Warden) spent six months in a British prison and modeled his character after the man in charge at that institution.