You take a capable, well-trained soldier with an iron will, and put him in desperate circumstances with equally desperate captors in a POW camp. The prisoner wants out at all costs. The captors want to hold him at all costs.
The result is often stories that seem too insane to be true. Yet...
5Three Men and a Pommel Horse
One of the most absurdly complex and overall ludicrous prison escape attempts in history is thanks to a pair of British pilots named Oliver Philpot and Eric Williams, who wound up in a Nazi prison camp along with another British soldier named Richard Codner. Philpot and Williams had been shot down during a bombing run, but it isn't exactly clear how Codner wound up there. Though, from listening to the guy, it is quite possible he voluntarily entered the prison just to see if he could break out. In his own words, "I enjoyed myself when we were escaping. We were really living then. I think it's only when you're being hunted that you really live... I liked being hunted..."
It wasn't the guards, guard dogs, or barbwire fences at Stalag Luft III that were the biggest problem inmates faced: it was the dirt. On top was dusty grey, but not far underneath was sandy yellow. Any yellow dirt that turned up in the prison meant a tunnel was being dug. Tunnels, like the three used in the Great Escape were being dug all the time, but most of these were discovered because of the amount of time and yellow dirt required to dig from one of the prison buildings.
There had to be a way around it. Together, the three men built a really big pommel horse (the rail with a pair of handles, like gymnasts use), capable of holding up to three men uncomfortably inside. Then they convinced the guards that they, and many other inmates, just loved the hell out of gymnastics. To make it convincing, they practiced for hours each day, despite the fact their rations, while adequate, weren't exactly chalk full of protein.
The men took turns hiding inside the horse; inmates carried it in and out to the yard, placing it in the same spot by the fence every day (Closer to fence = less dirt). From inside, a digger took the top layer of grey dust and placed it in a box. Bowls were used for shovels. So as not to leave a gaping hole in the yard, a board was placed over the hole and covered with the grey dust from the box. Guards walked right over it, and didn't notice.
The yellow dirt, meanwhile, was brought inside the prison with the digger, where it was disposed of in gardens, rooftops, and the toilet, Shawshank-style. The noise from digging, which would be picked up by microphones placed along the fence line, was attributed to the gymnasts leaping around the yard.
Just me and my leotards, no digging going on here...
Almost four months and many sweaty testicles later, the tunnel was ready. The three men punched through, assumed fake identities, and travelled across Europe, eventually making it to Britain via Sweden. As for the pommel horse and all those gymnasts back in the camp...we're sure they bear no hard feelings for leaving them there to rot.
4Airey Neave: Master of Half-Assed Disguise
Airey Neave was a British soldier who was wounded and captured by the Germans in World War II. He immediately picked up escaping as a hobby and at his second prison camp, Stalag XX-A, he escaped with a friend and nearly made it into Russian territory in Poland before being picked up and turned over to the Gestapo, better known as the biggest assholes of the war. For his transgression, Neave was sent to where all problematic POWs go: Oflag IV-C, the castle of Colditz.
Hermann Goering, the second biggest douche in Germany in the 1940s, declared Colditz "escape proof." Several prisoners, including Neave, set out to prove him wrong using various batshit insane methods.
One prisoner was sewn into a mattress in order to be smuggled out. Two others built an entire glider out of scavenged wood. Tunnels were also popular, but like each of these attempts, ultimately big fat failures (to be fair, the glider just didn't get finished in time).
Neave, perhaps wisely, settled on a subtler concept of escape. Finagling a Polish army tunic and cap, he painted them to look more like the Germans' uniforms. Then he proceeded to walk out the front door. Unfortunately, search lights reacted with the paint he'd used, making it shine a bright green.
Failure did not deter him. He tried the exact same plan five months later, this time using cardboard, cloth, and some more paint to make a more authentic-looking uniform. He and another prisoner, Anthony Luteyn, who had his own costume, just needed an opportunity.
That opportunity came in the form of an all-inmate stage show that was being put on at the prison (no, really). The two slipped under the stage, into a room that connected to a corridor which lead, not to freedom, but to the one place no prisoner wants to wind up: the guardhouse.
Wearing British uniforms over fake German uniforms over civilian clothing, the two lowered themselves into the room, ditched the British uniforms, entered the guardhouse, and pretended like they owned the place. Nobody noticed.
Having rehearsed their exit, they paused at the door leading out of the prison, exchanged a few remarks in German, and even put on their gloves before calmly leaving. The guards were completely fooled into thinking Neave and Luteyn were visiting officers. After passing through the courtyard and through the moat, they ditched their "German" uniforms and became two Dutch workers with papers, which were also fakes that gave them permission to travel from Leipzig to Ulm.
When they tried to buy train tickets for somewhere else, the police arrested them, later bringing Neaves and Luteyn to the foreign workers office because they really thought they were Dutch workers who had gotten confused; the duo split the moment the nice policemen weren't looking. Even when the Hitler Youth stopped them, Neaves and Luteyn remained composed and told another lie: They were Germans, from the north, of course. After this, Neaves and Luteyn kept to the country and travelled on foot. Hungry and a little frostbitten, they made it into Switzerland.
Neaves would eventually get back to Britain, where he would work to reinforce escape lines in Europe for other POWs. Later, he joined the International Military Tribunal at Nuremberg, where, in a freaking sweet turn of events, Neaves would personally serve Hermann Goering his indictment for being an absolute and total asshole.