Unbelievable Escapes That Defied All Odds: 8 Prison Breaks You Have to See to Believe

Throughout history, prisoners have staged some jaw-dropping, almost Hollywood-worthy escapes that make you wonder if they secretly moonlighted as stunt doubles. From a 17th-century Robin Hood-esque figure orchestrating daring jailbreaks that propelled him into folklore, to a notorious drug lord digging his way out of a fortress-like federal prison, these escape artists risked it all for the sweet taste of freedom. What drives someone to trade the predictability of a cell for the uncertain wild beyond? Is it sheer desperation or an indomitable spirit? Join me as we dive into the wildest, cleverest, and most audacious prison breaks ever pulled off — where danger, cunning, and a dash of insanity collide. LEARN MORE

Prisoners across history have devised surprising, often cinematic, escapes from the confines that hold them. Whether it be a 17th-century Robin Hood staging a series of folklore-inspiring prison breaks or a notorious drug lord tunnelling out of a maximum security federal prison, these escapees were willing to risk everything for their freedom. 

1. John Sheppard a.k.a. Honest Jack’s Daring Escapes 
2. John Dillinger’s Several Escapes
3. Rédoine Faïd’s Grand Prison Escapes
4. The 1983 Maze Prison Escape 
5. The 1962 Alcatraz Escape 
6. El Chapo’s Escapes
7. The 1864 Libby Prison Escape 
8. Ted Bundy 

John Sheppard a.k.a. Honest Jack’s Daring Escapes 

John Sheppard (later nicknamed Honest Jack on account of his popularity with the working class) was an infamous thief and petty criminal who escaped from London prisons an astounding four times in 1724. He was beloved for his charm, good looks, and the non-violent nature of his criminal activity; he was akin to a sort of Robin Hood of Georgian England. Sheppard’s spectacular escapes later made him the subject of countless works of art including an opera, multiple stage productions, and three feature films. 

Sheppard was a talented carpenter’s apprentice under the tutelage of his mother’s employer, William Kneebone. After falling in with a crowd of criminals and beginning a romantic relationship with a local sex worker named Elizabeth Lyon, Sheppard began stealing to supplement his legitimate income. He engaged in some petty theft, then began stealing from homes where he was working as a carpenter. He quit his apprenticeship in August 1723.  

After Sheppard, Lyon, and Sheppard’s brother Tom were arrested for a burglary they had committed in early 1724, Sheppard was imprisoned in St. Giles’s Roundhouse before escaping within just a few hours; he broke through the ceiling of his cell and lowered himself to the ground with a rope fashioned from bedding. Just a few weeks later, Sheppard was arrested again, this time for pickpocketing, and detained at central London’s New Prison alongside Lyon. Within days, the two were able to file through their manacles and escape from their cell using a rope fashioned from bedsheets—much like Sheppard’s prior escape from St. Giles’s. 

Sheppard returned to his criminal activity before being arrested once more in July 1724 at the direction of local crime boss Jonathan Wild. He was sent to London’s Newgate Prison, convicted of theft on August 12, 1724, and sentenced to death. But just days before his scheduled September 4 execution, Sheppard loosened a bar on his cell’s window and slipped through the gap while Lyon and another accomplice distracted the prison’s guards. 

Sheppard was able to hide out for a few weeks before he was eventually arrested again on September 9, 1724, and sent back to Newgate Prison, this time with additional security measures in place. Despite the increased security, Sheppard was able to bust free again by slipping out of his handcuffs and sneaking out of the prison. He disguised himself as a beggar and returned to London—and was then arrested for a fifth and final time on November 1, 1724, after burgling a pawnbroker’s shop. 

Sheppard was again sentenced to death (and monitored around the clock by guards) and scheduled to be executed on November 16, 1724. After his final attempt at escape was foiled, Sheppard was hanged on November 16, 1724, before a crowd of nearly 200,000 Londoners. 

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John Dillinger’s Several Escapes

John Dillinger was a Depression-era crime boss responsible for a string of bank robberies across the Midwest; he was among one of the many gangsters the public valorized during the Great Depression. Dillinger landed in prison for the first time after he and criminal accomplice Ed Singleton were arrested for the robbery of a Mooresville, Indiana, grocery store in early September 1924. The pair only made off with $50 (roughly $937 today)—but Dillinger remained in prison until he was paroled in May 1933 after serving more than eight years of his 10- to 20-year sentence.