Sure enough, as soon as he was left unsupervised in the library, Bundy jumped out of a second-story window and escaped. See, this is why we don't guard serial killers using the honor system anymore.

Wait, it gets worse. Within six months, Bundy was caught again and his trial resumed. At this point, legal advisers told him to stay the course, because the prosecution's case was weak and he was likely to get off. Despite this, Bundy devised a crafty if cliched escape by slowly sawing a hole in his cell's ceiling. Then, on Christmas Eve, he hid books under his blanket to imitate a body and escaped through the ceiling.

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*FOONT!* "Wheeeeee!"

It turns out that the ceiling led right to the apartment of the chief jailer, a situation that stupidly worked in Bundy's favor, because said jailer was out that night on a date. Bundy raided the guy's closet and stole his clothes, then simply walked out the man's front door to freedom, escaping to the retirement state, Florida. According to his later confessions, he intended to stop serial killing. Then, after he serial killed some more people, we executed the crap out of him. He really did forever ruin our ability to trust serial killers.

Vassilis Paleokostas is considered a kind of Robin Hood figure in Greece, although with a much less catchy name. Having committed a series of bank robberies and ransom kidnappings (and reportedly sharing his loot with the poor), his luck eventually ran out when he was caught and sent to prison. We can't say whether or not a corrupt wolf sheriff was responsible.

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From the story you're about to hear, this is probably closer to the mark.

But Paleokostas didn't stay behind bars for long. In 2006, he and an accomplice broke out, not through some daring Shawshank Redemption caper, but by simply getting his brother to land a freaking helicopter in the prison exercise yard and pick him up. The guards' excuse for allowing this insane plan to succeed was that they thought it was an impromptu visit from prison inspectors, given that nobody would be insane enough to try to escape prison in a helicopter. You know, because prison inspectors are more likely to make a surprise helicopter landing in the exercise yard and start lobbing smoke grenades at the staff.

The fugitives went right back to committing crimes until they were recaptured two years later. But it didn't last this time, either -- Paleokostas and his henchman were still days away from being tried for their previous escape when, in February of 2009, they escaped from the same prison a second time (and yes, we're serious) in another helicopter.

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"There is elegance in simplicity. And also in helicopters."

Greek authorities are understandably a little embarrassed by this, and Paleokostas remains at large. You have to admit, it really doesn't seem like the sort of thing that would happen twice.

Charles Victor Thompson was sentenced to death for murdering his ex-girlfriend in 1998. In 2005, he decided that death row wasn't his scene, so he planned a brilliant escape. It's very similar to the ingenious plan from The Shawshank Redemption, with a couple of variations.

First, just like Andy from the movie, Thompson smuggled civilian clothing into his cell so that after he was out he could walk around without looking like an escaped fugitive. Second, he had to get out of the building itself. Now, here's where you might be expecting us to say that he carefully tunneled through his cell wall over several years, but Thompson's plan was actually much easier. He scheduled a meeting with his lawyer and, when the lawyer was out of the room, quickly changed into his second set of clothes. Then, he escaped the cell via a precise method known as "walking out of it, because it wasn't locked."

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"Hey, you, sto- oh, never mind. I didn't realize you were a totally normal civilian, as denoted by your manner of dress."

But he wasn't out of the woods yet, and now was time to activate phase two of his brilliantly orchestrated escape. When he headed toward the prison exit, he was stopped by the guard at the front desk. Thompson had prepared for this eventuality by doing absolutely nothing at all, so he lamely flashed his inmate badge and told the guard that he was with the attorney general's office.

The guard took a long look and said, "I've never seen one of those badges before." You know, a regular inmate badge from the prison that he was employed to guard. Rather than ask any more uncomfortable questions, he let Thompson walk out to freedom. Don't worry, Guys Who Were in Charge of Keeping This Murderer from Escaping, you were beaten by the best.

Via Deathrow-usa.com
This guy.

Thompson was later recaptured when, after hopping a freight train to East Texas, he made the questionable decision of going to a liquor store and getting s**t-faced drunk. In the end, his only real crime was a love of beer. Also, murder one.

Alfie Hinds was a professional British jewel thief who gained celebrity in the mid-20th century for his repeated prison escapes -- he broke out of three different high-security prisons, maintaining the whole time that he was totally innocent. It turns out that using your impressive jewel thief skills to break out of prison is a bad way to prove that you're not some kind of jewel thief.

The first time he escaped, Hinds managed to simply unlock the prison doors after memorizing the shape of the key and making himself a copy. He was caught again eight months later, and this time they decided it was best not to show him what the key looked like.

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"Just let him go, man. He deserves it."

Hinds' second escape came after he filed a lawsuit against his arresting officers for what he claimed was an illegal arrest. But this was an absurd ploy. When he was taken to the courthouse, he asked to use the restroom, but he had already arranged for accomplices to leave a padlock next to the bathroom door. When Hinds' guards removed his handcuffs so he could drain the lizard, he promptly grabbed both guards, threw them into the bathroom stall, and slammed the door shut, padlocking it behind them. Then he ran away like Daffy Duck.

After years of bouncing in and out of the big house, Hinds finally "escaped" prison for good, this time legally. Apparently, he was also some kind of law prodigy, and was able to manipulate a legal loophole to get out of more prison time, even though he was obviously guilty. After this whole mess, the law was changed to prevent this kind of thing from happening again, and Hinds was rewarded with fame and fortune for being little more than a lucky jerk with some law books.

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He actually sued the guy who arrested him. No joke.

In 1987, Richard Lee McNair killed a man and wounded another while attempting to rob a grain elevator in North Dakota (because what else are you going to rob in North Dakota?). The state gave McNair two life sentences and then proceeded to utterly fail in keeping him there. Over the next couple of decades, McNair escaped from two prisons and one county jail, and showed up on America's Most Wanted so often that they may as well have made him co-host.

The first escape was from a police station jail in 1988. Sitting in a room with three detectives, McNair used lip balm to grease his hands up enough to escape from his cuffs, and then got out somehow and made the cops chase him around town in a scene we can only assume was accompanied by "Yackety Sax."

AMW via Castanet.net
Now that is the wacky face that comedy is made of.

Four years later, McNair escaped from a state penitentiary by crawling out through the ventilation ducts, something we thought was only possible in movies. After that, he evaded police for 10 months before they caught up with him and locked him back up, this time in a maximum security federal prison. Unfortunately, McNair just saw this as a challenge.

In 2006, McNair got himself a job in prison repairing mail bags, and he took the opportunity to climb inside one and mail himself out of prison. After being forklifted to a nearby warehouse, McNair dusted his hands off and simply walked away.

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"Um, sir, this one ... farted."

To make things even worse, McNair was spotted hiking along a railway line, questioned, and let go by a police officer later on the day of his escape, an event that was caught on video. How did he get away this time? Despite the fact that he gives two different names during the course of the conversation, has no identification, and matches the description of the escaped convict that the cop is looking for, the officer simply gives him some pointers on railroad safety and sends him on his way. So, apparently, he used a Jedi mind trick.

McNair was eventually caught again and is currently back in prison. At least that was the situation at the time this was written. It might have changed by now.

For more incredible acts of crime, check out 5 Real Bank Heists Ripped Right Out of the Movies and 5 Real World Criminals Who Were Certified Supervillains.