#1 - Alcatraz
Probably the most famous and daring prison escape ever committed. Frank Morris, Clarence and John Anglin broke out of the infamous Alcatraz prison in 1962. They used a series of Tools including a drill that was made from a vacuum cleaner’s motor. The three inmates chipped away the concrete walls in their cells to escape into a nearby ventilation shaft, before making their way from the ventilation shaft onto the beach where they then escaped on a homemade raft to the San Francisco bay. Nobody knows for sure whether they made it or not as they where never heard from again and no bodies were ever found.
#2 - Stalag Luft III
In 1944 during WWII 76 allied soldiers escaped Stalag Luft III German prison by digging three tunnels 30 ft. under it using construction methods that included wood blocks for support and a series of lamps and pumps to make sure the soldiers had air to breathe while they dug. Despite their preparation the soldiers ended the tunnel just short of the forest and in plain sight of the guards outside of the gates. While 76 managed to escape, the 77th was spotted, which started a massive manhunt where all but three of the escapees were caught. The 1963 movie 'The Great Escape' starring Steve McQueen was based on this real life prison break.
#3 - John Dillinger
Infamous criminal John Dillinger led one of the most impressive and successful prison escapes of all time. After being arrested in 1934 he was sent to Lake County Jail which at the time had the reputation of being 'escape proof' and then making a fake gun out of a bar of soap managed to steal the Sherriff’s car before fleeing to Illinois where he was killed by the FBI who eventually caught up with him.
#4 - Joaquin 'El Chapo' Guzman
This Mexican drug barons ability to elude capture is legendary. In 2015, after spending a little over a year in prison following 13 years on the run the billionaire head of the powerful Sinaloa Cartel fled via a mile long tunnel that ran from his cell to a building under construction outside the prison's perimeter. A massive manhunt was launched and El Chapo was eventually caught and put back behind bars again.
#5 - Parkhurst Prison
Parkhurst prison on the Isle of Wight is considered to be Britain's answer to Alcatraz. In 1995 Keith Rose, Andrew Rodger and Matthew Williams were serving time for crimes that included murder and planting a bomb when they escaped the correctional facility using a key they had cut themselves. They used the key to open a series of doors, then cut through a mesh fence and scaled the perimeter wall. They took a taxi to the town of Sandown, where they spent four days trying to steal planes and boats to get off the island while sleeping rough in a field. The three men were eventually discovered by an off-duty prison officer.