Criminals who are sent to Prison are guarded 24 hours a day, seven days a week. The amount of security most prisons have should be enough to keep Inmates from escaping. However, sometimes the highest walls aren’t enough to contain the most determined criminals who want an early taste of freedom and cause occasional break outs.

More interestingly though, is the fact that some criminals are able to escape from prison not just once, but several times. Here are the criminals who were so talented at escaping from prison that they were able to accomplish the unthinkable feat more than once.

Pascal Payet escaped jail with the use of helicopters

This convicted murderer has become infamous for escaping prison, Hollywood style, and used helicopters as the vehicles of his choice to jailbreak from the facility.

Payet arranged for a helicopter to land on a roof of the prison to pick him up in 2001. In 2003, he hijacked a chopper and used it to break out three more inmates from the same prison, only to be recaptured three weeks later.

In 2007, he made a daring escape for the second time and used his connections from outside the prison to arrange for a helicopter to be hijacked. Three armed men attacked the state penitentiary with the use of the 'chopper' and were able to take Payet with them as they escaped.

Payet was captured again in Spain three months later and has remained in prison ever since.

Willie Sutton disguised as a prison guard to escape

Sutton was a convicted robber who was very talented at committing bank robberies using disguises that earned him the nicknames, “The Actor” and “Slick Willie.” However, committing robbery is not his only talent as he also had a knack at escaping prisons.

After being sent to prison for assault and robbery in 1931, he was able to escape prison after only one year. Sutton was able to scale the prison wall by using two ladders and remained on the run for two years before authorities caught up with him.

Sutton’s next attempt at freedom was successful by going through a tunnel, although he was captured the very same day.

His last successful attempt at escaping prison came in 1947 where he dressed up as a prison guard and again used ladders to scale the prison walls. Sutton’s name was added to the FBI’s top ten list of wanted fugitives in 1950.

In 1952, he was captured by authorities but was released from prison in 1969 due to his deteriorating health. Sutton died a decade later.