Breaking out of a prison is no easy feat. Many prisons have security features such as CCTV, motion detectors, barred windows, massive walls, barbed wire, electric fencing, and armed guards. Despite these and other obstacles, some prisoners will exhaust the limits of their wit and ingenuity and take every opportunity they can to escape. Prison breaks have been a part of our pop culture since before the days of 19th century western outlaws. Like in Hollywood, it’s sometimes difficult to decide who the good guys are and who are the antagonists. Regardless, we all love a good chase.
10. Jack Sheppard
Jack Sheppard enjoyed near celebrity status in 18th century London for his multiple prison escapes. Though he apprenticed as a carpenter, in 1723 he decided that a life of crime was a more rewarding way to make a living. In 1724, he escaped from prison four times.
Sheppard escaped within three hours of his first arrest. He broke through the ceiling and lowered himself to the ground with a rope made from bed sheets. Three weeks later he was arrested again. This time he removed a bar from the window and performed the same bed sheet stunt. He was arrested a third time and sentenced to death. On the day of his execution, he loosened a bar from his window and escaped wearing women’s clothing. After his final capture, Sheppard was secured with 300 pounds of iron weights and placed under constant surveillance. He was executed on November 16, 1724.