Breaking out of prison is no easy task unless you are a criminal mastermind like Prison Break’s Michael Scofield. Even for Scofield, things were not s easy as he got caught multiple times. In real life, there are lots of successful prison breaks though, like that of El Chapo Guzman, although he was caught and is now serving life in a maximum-security prison in the US. So, does anyone really ever escape from prison? Well, many try, and may end up getting caught. Here is a look at the most hilarious failed prison breaks ever.

The Guy That Got Stuck In The Hole

Remember in Prison Break season one when the fattest guy caused the line to fall? That is exactly what happened to Rafael Valadao when he and his friends dug a hole in the prison wall to escape in 2012. The plan was for the four of them to jump through the hall and make a run for it in the dead of the night. The first guy managed to get through the whole. Rafael was the second in line but he had a huge belly that got stuck in the whole. Efforts by the two guys behind him only got him more stuck causing him to scream for help as his ribs snapped. The prison had to call firefighters to rescue him and take him to the hospital. He became a celebrity as videos of his thwarted escape attempt made circles online.

The Guy That Sent His Escape Plan To The Wrong Address

If you want to break out of prison, you have to be super smart and you may need some luck on top of that. Then comes the most important part, discretion! That is the one thing Sean Castorina of Alamance County prison lacked. He had conspired with two other people to blow up the walls of a prison in 2018, just a year into his 13-year prison term. After getting the plans for the prison and drawing up instructions on how to increase the impact of the bomb, he mixed up the addresses and got the letter mailed to the wrong person. The woman that got the letters sent it straight to the police ending the convicted murderer’s planned escape.

He Didn’t Know How To Walk In Heels

In 2013, Clauvinho Da Silva managed to escape from a prison in Brazil alongside 30 other prisoners but was recaptured and taken to a maximum security facility. However, he couldn’t stay in prison. He tried again in 2019, this time, by getting several people to bring him items he could use to disguise himself as his 19-year old daughter. After his daughter had visited him, Da Silva, armed with a silicon mask, a long black wig and heels tried to walk right past the guards. He was nervous and had trouble balancing on his heels which caught the guard’s attention. He was caught and taken back to prison where he was serving 73 years. He committed suicide a week later.

Too Out Of Shape To Climb

Planning is not the only thing you need when escaping from prison. Even with the best plan, you have to be in good shape to execute it. Frank Arthur and Clayton Musselman drew a perfect plan for getting out of Henrico County Jail East. Their plan of escaping at 9 pm worked until they got past the exercise yard to the fence. The problem is that both prisoners were extremely out of shape so that run across the yard took a toll on them. They were unable to make the final climb over the fence which was high and both of them were getting cut by razor wire. They gave up and sat in the yard to catch their breath as they waited to be caught.

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Take A Zeppelin Out

Drug dealers are some of the hardest people to keep in prison as most of them have money and strong allies on the outside. The prisoner in this case was known as Giulio B, an Italian drug trafficker imprisoned on Spain’s Canary Islands. Giulio had his allies set up a camp 600 meters from the prison, then send in a remote-controlled zeppelin loaded with climbing equipment and night vision goggles. He was planning to climb over the wall and into a waiting car somewhere near the prison. The Zeppelin was too big and conspicuous though, leading to Giulio’s quick arrest before he could get anything to help him escape.

I Really Have To Take A Nap

This is also known as the guy escapee who slept. Robert L. Emery made news all over the US in 2013 when guards found him tucked under a blanket in the yard after he tried all night to escape. He was convicted of robbery, kidnapping, attempted rape and assault in 2000, so he is not getting out of prison until 2060. However, in July 2013, he decided he had had enough and tried to escape. He managed to get into the prison maintenance rooms, get dinging tools and even break past two doors. He then dug under the first fence and scaled the second where he was cut. He decided that he was too exhausted to move and chose to sleep in the yard awaiting his fate.

Stuck In The Sewers

In 2013, a mass prison escape in Brazil through the sewer system shook the world. However, in this case, the sewers were very useful in keeping someone in prison. One man was trying to escape a prison in 2015 using the communal toilet when he got stuck in the pipes. It was a messy attempt that ended hilariously badly with his entire body covered in poo. He also had to be rescued as his plot was only proving futile and dangerous. As usual, the guards shot a video of the attempt and shared it with the world.

Take The Trash Out

Prisoners who work in the kitchen feel rather unlucky because the trash they take out gets past the gates every day but they can’t. 24-year-old Sydney Da Cruz and his 18 year old friend Carlos tried to be taken out of Delegacia De Furtos prison in Southern Brazil alongside the trash. They hid in the trash bags hoping to be carried out by the maintenance staff, but that requires lots of patience that the two didn’t have. The guards noticed “more than normal” movement in the trash and decided to check out. Of course, the trash had to go back inside afterwards.

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Can I Have A Ride

Allen Lewis, a prisoner in Greenup County Jail, Kentucky was being transferred to prison by an officer when he plotted a James Bond-style escape. He complained that his cuffs were too tight, so the officer stopped to adjust them. After getting one free arm, Lewis wrestled the officer, overpowered him and took off. He was on a highway, so he attempted to flag down a car and on did. A police officer stopped and offered Lewis who was attempting to hide cuffs a ride. Lewis ended back in jail having become a celebrity as his plan failed.

Crashed

So, back in the 80s in the US, marijuana smuggling was a huge crime and you could get life in prison for it. That is the sentence Ben Kramer, former powerboat racer and a part time bhang smuggler was serving at the Metropolitan Correctional facility in Miami in 1989 when he decided he couldn’t have it anymore.

He had his accomplices get a chopper to land in the yard right in front of the guards. The pilot was a novice though, so as he was taking off, the propeller hit the fence and down came the bird. The pilot suffered broken legs while Kramer broke his ankle so they had to be flown to a hospital before becoming prison mates.