An airing of the movie on a Starz channel occurred the exact same night that two convicted killers escaped from a maximum-security prison in upstate New York. What's more, the men used several tactics seen in this movie, such as the Sleeping Dummy.
Magnificent Bastard: Frank Morris is a real life example. He masterminded the escape from this supposedly inescapable prison island with the Anglin brothers without a trace and became a legend. Even better, MythBusters found his chance of success plausible.
Moral Event Horizon: Dear God, this is not how a prison warden should behave! Yet sadly, the Warden crosses it in his zeal to control the prisoners, to the point where Umbridge may have learned a thing or two from him in running Hogwarts.