Felice Benuzzi was a P.O.W. in Kenya during WWII. He recruited two others to stage an escape so that he could climb the second highest peak in Africa, knowing that there was no chance of a permanent escape. With scant food and only improvised equipment such as barbed wire crampons, no porters or guns, they traversed the jungle, encountering wild animals, and climb the mountain. Two of them reached a point ~5000 m high on the 5199 m mountain. And then they returned and broke back into the camp, as planned. He later wrote the book based on this, which was made into a fictionalized movie.
In order to escape arrest, a man feigned a heart attack. After being placed under a security watch in a hospital, he impersonated an FBI agent on the phone and told his guards he could be released.
A man escaped from a German prison by hiding in a cardboard box, which was then taken outside of the prison by courier.
The American gangster John Dillinger escaped from jail with a wooden pistol. After whittling it in his cell, in March 1934 he used the fake weapon to intimidate 33 people before getting a real machine gun. “Ha, ha, ha! And I did all this with a wooden gun!” he bragged while leaving.
15 monkeys escaped a primate research center in Japan by using trees as catapults over a five-meter high electric fence and afterwards were lured back with peanuts.
Steven Jay Russell impersonated a prison guard to simply walk out of prison. Upon recapture Russell lowered and paid his bail by pretending to be a judge, escaped his next capture by impersonating a doctor, and did so AGAIN by faking his death, eventually landing him a 144yr sentence.
Mike Kurtz, an American burglar, found out that eating common soap could produce the effect of ill health. His sudden and unexplainable weight loss and other symptoms baffled the prison doctors and he was able to fool officials that he was dying and received a pardon.
British WWII prisoner of war John Fancy dug eight tunnels with a table knife and escaped a total of 16 times, but was always recaptured.
In 1986 a convict escaped during a prison transfer. A week later he returned in a stolen helicopter and broke out his girlfriend.
A man faked mental illness to escape jail, was sent to an asylum and has been trying since to convince doctors he’s sane. He’s been diagnosed a psychopath ’cause in part, “Faking mental illness to get out of a prison sentence is exactly the kind of manipulative act you’d expect of a psychopath.”