The greatest and most audacious prison breaks in history

El Chapo being led away by two special forces officers
El Chapo was able to escape from prison twice, but was recaptured on both occasions | Image: Octavio Hoyos / Shutterstock.com

From underground tunnels to ingeniously decorated fruit, some of the most daring criminals have been willing to try anything to get free. Despite their dodgy pasts, it’s hard not to be fascinated by the lengths these convicts have gone to escape staying behind bars.

Academy Award-winning actor Morgan Freeman joins Sky HISTORY to cover eight of the most audacious and mind-blowing prison breaks from history. Great Escapes with Morgan Freeman delivers a fascinating and insightful look at each real-life story, including the infamous Alcatraz attempt, El Chapo’s tunnel, and James Earl Ray’s spell on the run. New episodes air every Wednesday at 10pm.

Many of the most famous prison breaks have been recreated or embellished on the silver screen, but some of these stories are so unbelievable they haven’t quite made it that far. Let’s look more closely at some of the most audacious, dare we say, impressive (and unbelievable) prison breaks of all time.


Ronnie Biggs – Robber on the Run

Despite his criminality, Ronnie Biggs holds a kind of legendary status for many of us. Infamous for his role in The Great Train Robbery of 1963, Biggs remained on the run for 36 years living as a fugitive across the world. Sentenced to serve his time at Wandsworth Prison, Biggs scaled the walls with a rope ladder on 8th July 1965.

Once on the road again, Biggs changed his appearance with plastic surgery, acquired a new identity in Paris and moved from country to country avoiding the law. Most of his years were seen out in Australia and Brazil. Finally, on 7th May 2001, Biggs made his way back home and served eight years in prison before being released on compassionate grounds in 2009, aged 80.


Michel Vaujour – Forbidden Fruit

Working with his wife as an accomplice, bank robber Michel Vajour went to unusual lengths to plot his escape. In 1986, Vaujour used a fake pistol and nectarines painted to look like grenades to force his way onto the prison roof. His wife then picked him up in a helicopter (which she’d spent months learning to fly), and they landed nearby.

It’s hard to imagine a painted nectarine looking anything like a grenade, but it managed to fool the French prison guard. Both Michel and his wife were caught and arrested after their unique and creative prison break.


El Chapo – Snakelike Skills

Even maximum security jail wasn’t enough to keep Mexican drug lord Joaquin ‘El Chapo’ Guzman contained. In July 2015, El Chapo escaped via an inexplicably small 20” hole in the shower area of his cell block, before making his way along a lit and ventilated tunnel system.

This wasn’t even his first prison break. His other successful attempt involved hiding in a laundry cart in 2001. With a strong network of others on his side as a leading figure in the Sinaloa drug cartel, El Chapo could always rely on others to help him break free. He managed six months on the run before being recaptured in January 2016.


Ronaldo Silva – Dude Looks Like a Lady

Ronaldo Silva took DIY disguises to a new level when escaping from Penedo Prison in Brazil. The drug trafficker opted to try out a surprising new look to find a way out of his sentence. After his wife brought him an extra outfit, along with a wig, shoes and bright red lipstick, Silva began his transformation. Amazingly, the couple managed to swap clothing, and Silva even deigned to shave his legs before walking straight out of the prison’s front gates.

Sadly for him, his attempt didn’t get him too far, as he was spotted almost instantly by a police officer. The officer remarked on his “funny walking” as Silva hadn’t quite mastered the heels. So back to prison he went.


The Great Escape – The Greatest Escape

No comprehensive list of amazing prison breaks is complete without special mention of The Great Escape. While the Steve McQueen film of the same name is known to be quite a stretch from the original story, 1944 did see 76 allied airmen escape the Nazi Prisoner of War Camp at Stalag Luft III. It remains one of the most inspirational tales of bravery from the Second World War.

The daring and ridiculous come together when convicts get creative and look to find a way out of their unfortunate circumstances. Even the highest security prisons still have try-hard escapees determined to use whatever means they can to find a way out. But, as we’ve seen, most of them end up back inside before long, and their escape attempts become the stuff of legend.