Even A Cage Couldn't Hold Them

Jailbreaks tend to stick in your memory because they combine bold planning with high-stakes chaos that’s hard to ignore. Some became famous for ingenious methods, others because the escape set off huge manhunts, and a few because the ending still isn’t fully settled. They also reveal an uncomfortable truth: “secure” doesn’t always mean “secure enough.” Here are 20 of the best-known breakouts people still talk about.

Public Record Office of Northern Ireland on Wikimedia

1. Alcatraz Escape (United States, 1962)

In June 1962, Frank Morris and his brothers, John and Clarence Anglin, carried out the most famous escape tied to Alcatraz. They used dummy heads to fake sleeping bodies, slipped through a service route, and headed toward San Francisco Bay on a homemade raft. No one has proven exactly what happened after they hit the water, and that mystery keeps the story hot. 

US Federal Government on Wikimedia

2. The Great Escape, Stalag Luft III (Germany, 1944)

Allied POWs spent months digging tunnels and coordinating supplies for a breakout in March 1944. Seventy-six men made it out before the escape was fully discovered and shut down. Most were recaptured, and the aftermath was grim, which is part of why the event remains so well known. 

Lt. Robert M. Polich, Sr. Photograph: Kevin Rofidal on Wikimedia

3. Colditz Castle Escapes (Germany, 1940–1945)

Colditz was a Nazi high-security prison designed to hold repeat escape artists, which basically guaranteed nonstop attempts. Prisoners tried disguises, forged documents, hidden routes, and an impressive range of plans that varied from clever to wildly bold. Several inmates did manage to get away, even though the castle’s reputation was “escape-proof.” It became famous because the ingenuity never really stopped.

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4. Casanova’s Escape from the Venetian “Leads” (Italy, 1756)

Giacomo Casanova escaped from Venice’s notorious Leads prison in 1756, where he was being held in one of the top-floor cells, and he later described it in detail. His account helped turn the escape into a legend partly because he wrote like someone who enjoyed being the main character. Putting his large ego aside, though, the prison’s harsh reputation was very real, and the escape was truly impressive.

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5. George Blake Escapes Wormwood Scrubs (United Kingdom, 1966)

George Blake, a British intelligence officer who spied for the Soviet Union, escaped from London's Wormwood Scrubs in October 1966. He had help from outside contacts, and the whole episode turned into a major embarrassment for authorities. After getting out, he made it to the Eastern Bloc and stayed beyond British reach for decades. 

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6. Dannemora Escape, Clinton Correctional Facility (United States, 2015)

In June 2015, Richard Matt and David Sweat escaped by cutting through walls and navigating utility areas into the prison’s infrastructure. The manhunt that followed was huge and lasted weeks, pulling intense public attention. One escaped inmate was killed during the search, and the other was captured not long after, but the planning still shocked people. It’s a modern example of how complicated prisons can hide weak spots.

Bubby1124 on Wikimedia

7. El Chapo’s Tunnel Escape, Altiplano (Mexico, 2015)

Joaquín “El Chapo” Guzmán escaped in July 2015 through a tunnel connected to the shower area. Reports described a tunnel that seemed engineered for speed and efficiency, which raised serious questions about inside help. Because he was such a high-profile criminal and the escape was so outrageous, it caused international headlines and renewed concerns about corruption and security failures.

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8. Libby Prison Tunnel Escape (United States, 1864)

Union officers held at Libby Prison in Richmond dug a tunnel and escaped in February 1864. More than 100 prisoners got out in the initial rush, making it the largest Civil War escape. Many still faced dangerous travel and recapture risks, so getting out was only the first hurdle. The escape is remembered for both its scale and its nerve. 

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9. Maze Prison Escape (Northern Ireland, 1983)

On September 25, 1983, thirty-eight IRA prisoners escaped the Maze Prison, one of Europe’s most secure facilities at the time. The operation involved coordination, deception, and violence as the escape unfolded. Its political impact was enormous, and the story spread far beyond the UK and Ireland. When people talk about “biggest” modern European breakouts, this one is always mentioned.

Public Record Office of Northern Ireland on Wikimedia

10. Punta Carretas Mass Escape (Uruguay, 1971)

In 1971, more than 100 prisoners escaped from Punta Carretas prison in Montevideo through a tunnel. The escape is famous for its scale and for the organization required to pull it off without immediate collapse. It’s also remembered because some involved later became significant public figures. Few breakouts are both gigantic and historically consequential in that way.

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11. Storming of the Bastille (France, 1789)

The Bastille was seized in July 1789 during the French Revolution, and the prisoners inside were freed. The number of inmates was small, but the symbolism was massive, which is why it’s still treated like a landmark “jailbreak” moment, even if it's remembered less as a prison story and more as a spark for political upheaval. 

Jean-Pierre Houël on Wikimedia

12. Winston Churchill’s Boer War Escape (South Africa, 1899)

Winston Churchill escaped from a Boer POW camp in Pretoria in 1899. He slipped away and then traveled in hiding, relying on help and quick judgment to avoid being caught again. The story boosted his public profile early, long before he became England's most famous Prime Minister.

Yousuf Karsh on Wikimedia

13. John Dillinger’s Crown Point Escape (United States, 1934)

In March 1934, John Dillinger escaped from the jail in Crown Point, Indiana, in a breakout often linked to a fake gun. The humiliation factor was huge because the facility was touted as super secure, and he still walked out. He even stole a sheriff’s car during the escape.

FBI on Wikimedia

14. Ronnie Biggs Escapes Wandsworth (United Kingdom, 1965)

Ronnie Biggs, one of the Great Train Robbers, escaped from Wandsworth Prison in 1965 with outside assistance. The case fed a media frenzy because the robbery itself was already famous, and the escape added another dramatic chapter. Biggs remained a pop-culture fixture for years, which kept the story circulating. 

Buckingham Constabulary on Wikimedia

15. Charlie Wilson’s Escape (United Kingdom, 1964)

Charlie Wilson, another figure tied to the Great Train Robbery, escaped from prison in 1964 after help arrived from the outside. The breakout reinforced the idea that this group was determined to embarrass the system at every turn. 

Edwin S. Porter on Wikimedia

16. Mountjoy Helicopter Escape (Ireland, 1973)

In 1973, in what was probably the most audacious jailbreak ever, a helicopter landed in the exercise yard at Mountjoy Prison in Dublin, allowing prisoners to escape in a move that sounded unbelievable even as it happened. The visual alone made it famous, because it looked like something security definitely should’ve prevented. It also showed how a bold plan can exploit a place’s routines and blind spots. 

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17. Strangeways Riot Escapes (United Kingdom, 1990)

During the Strangeways prison riot in Manchester in 1990, chaos created openings for some inmates to get out. This wasn’t a quiet, carefully timed plan so much as a breakdown in control that spilled into opportunity. The event became infamous because it highlighted deep problems inside the prison system, not just one clever escape. 

Peter McDermott on Wikimedia

18. Parkhurst Prison Escape (United Kingdom, 1995)

In 1995, inmates escaped from HM Prison Parkhurst on the Isle of Wight, a facility known for holding high-risk prisoners. The breakout drew attention because it revealed security weaknesses in a place that was supposed to be exceptionally hard to breach. The inmates were recaptured four days later, but the fact that they got out in the first place spiked public concern.

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19. The Texas Seven Escape (United States, 2000)

In December 2000, seven inmates escaped from a maximum security prison facility in Texas and stayed free for weeks. The case became infamous because the group committed serious crimes after escaping, turning it into a public safety crisis. The manhunt was intense, and the story dominated the news for a long stretch. It’s remembered as much for what happened afterward as for the escape itself.

Nick DiFonzo on Wikimedia

20. The Escape of Napoleon III from Ham (France, 1846)

In 1846, Louis-Napoléon Bonaparte, later Napoleon III, escaped from the fortress prison of Ham, where he was being held after a failed coup d'état. He reportedly used a disguise to slip out and avoid immediate capture, then made his way to safety. After his escape, he returned to politics and became Emperor of the French, which made it all the more significant.

Franz Xaver Winterhalter on Wikimedia