Eddie Chapman was a criminal, a thief and a womaniser, getting into trouble and living the high life in England in the 1930's. He schmoozed in various social circles, getting more babes than David Beckham, sleeping with them and then blackmailing the chicks with naked pictures he secretly took of them. When he wasn't extorting money from wealthy or semi-wealthy adulteresses and babes of all shapes and sizes, he spent his time cracking safes and pulling off heists and capers for some extra dough. He fashioned himself as a sort of "Prince of the Underworld" - he was smooth, headstrong, cocky and probably carried a badass purple fuzzy pimp-cane.
Eventually his luck ran out, however. He was busted in Edinburgh for blowing the safe of a large bank, which is the sort of thing that can get you into deep shit. In an attempt to avoid Federal pound-me-in-the-ass prison he skipped town, heading off to the island of Jersey where he promptly got arrested again for blowing the safe of a bitchin' dance club.
Then the Germans came to visit. The Nazi Empire stormed through the French countryside in 1940, capturing Paris and forcing France under the heel of some munchy crunchy good old-fashioned Fascism. When the Nazis took control of Jersey, they moved Chapman to a prison on the mainland of France and threw away the key. Not that it mattered to him, course; he used his skills as a level 20 Thief to fashion a skeleton key MacGuyver-style out of hairpins and soap that allowed him to escape from his cell every night, make his way over to the women's prison that was attached to the men's prison and get busy with some criminal babes. A little thing like being locked in a fucking Nazi prison wasn't going to stand in the way of Eddie Chapman and a building full of moderately attractive chicks.
Once the Germans figured out what was going on, they decided to offer Chapman a job as a secret agent working for the Nazis against the British jerkmeisters that had thrown him in prison to begin with. Seeing an opportunity for adventure, and to get out of his fucking dank-ass boring cell, Chapman agreed to go to work for the Führer. He was released from prison and parachuted into England with a critical mission: To sabotage and destroy the British factory where Mosquito bombers were being produced, and then to make his way back to the Fatherland.
Eddie Chapman glided softly into Hatfield, England late one night. He stealthily made his way through the countryside towards his target. Then, instead of blowing up the factory as he had been instructed to do, Chapman did something his German handlers didn't expect. He went right in the front door of MI-5, the British Intelligence Agency, and told them what was going on. The British government saw the beginning of a beautiful relationship.
Thus Eddie Chapman was dubbed "Agent Zigzag" - a double agent working for England against the Nazis, who in turn thought he was working for them against the British. I think. MI-5 faked an explosion at the Mosquito factory, planted a story in the newspaper, and then sent Chapman back to Berlin where he was received as a hero by the Third Reich. Chapman received the Iron Cross, the highest German award for bravery, was given a free yacht, 110,000 Reichmarks and was sent to Oslo, Norway to be an instructor at a Nazi spy school. He worked for a couple of months at the training facility, presumably giving really ridiculously bad advice to future Nazi spies, but after the Allied invasion at Normandy he was once again called back into action for the Fatherland. The Germans parachuted Chapman into England, set him up with a radio, and asked him to help verify the accuracy of the V-2 rockets they were launching at the British mainland. Of course, Chapman fed them more misinformation, and totally fucked up the calibration of the Nazi missiles.
Eventually things got too hot so the Brits bought out Chapman's contract and gave him an early retirement and forgave all of his prior criminal transgressions, which is totally fucking sweet. He spent his post-war years as he spent the earlier ones - living it up, sipping cocktails till early in the morning, seeking adventure, and chasing skirts like Pepe Le Pew after a long night of booze and cocaine. He passed away in 1997 at the age of 83, spending his later years as the owner of British Health Spa.
Eddie Chapman is proof that you don't have to be a muscle-ridden face-smasher to be a badass. He wasn't a big guy, he wasn't a killer, and he never fought when he could evade. But he still managed to become one of the most colorful war heroes in British history, playing both the Brits and the Germans off each other, getting into all sorts of adventures, pulling all kinds of box, and being pretty much everything you could hope for in a professional spy. As one of his former bosses once said, "Chapman loved himself, loved adventure and loved his country, probably in that order."