A successful prison break requires resourcefulness and more than a little luck. It’s not the sort of activity that should be tried by anyone at all, let alone inmates with far more bravery than smarts. But that doesn’t mean people of all sorts of mental capabilities haven’t given it a shot anyway. Do you know someone that may be hiding a criminal past? Search here.

Here are 13 of the most dimwitted attempts to break out of prison!

1) Brazilian Man Tries To Escape In Drag

It’s shocking to think that such a perfect disguise didn’t fool the security guards, but somehow Ronaldo Silva’s dream of escape was foiled. He and his girlfriend came up with the plan to sneak out in drag after she visited him in prison. He put on her clothes, a wig, and some makeup and tried to walk out of the prison like he was just another visitor. He even managed to make it past a few guards, but was given away when one astute guard noticed that “she” was having a difficult time walking in high heels.

2) Man Successfully Escapes, Until He Knocks On a Prison Guard’s Door

James Edward Russell, having served no fewer than four prison sentences, no doubt spent of a lot of time contemplating the logistics of his escape before he finally tried. The plan to break out of the Olympic Corrections Center was as simple as it was foolproof. Russell would simply break out of the minimum security facility, innocently ask to borrow a phone from the first house he came across, and then hitch a ride far away from the prison.

Everything was going flawlessly up until he fled to a cabin near the the prison. After he knocked on the door, it wasn't a kindly old man who was eager to let him use his phone, but a prison guard who worked at the very same prison Russell had just escaped from. After a brief fight, the fugitive was brought back to the facility and faced more time for the attempted escape.

3) Brazillian Gets Stuck In Escape Hole

Rule of thumb for making an prison tunnel: make sure you can actually fit through it before you attempt to escape. Four Brazilian prisoners forgot this very simple guideline when they tried to bust out of a penitentiary by knocking a hole in the prison shower. The first would-be escapee managed to fit through, but when the second tried to squeeze out to freedom, he got stuck at the waist, trapping the remaining two prisoners inside. Prison guards found him screaming and crying for help. Not wanting to waste such a ridiculous scene, they took pictures while waiting for the fire department to help free the man.

4) Man Tries To Use Zeppelin To Escape Jail

Well-connected prisoners occasionally try to break out with the help of a helicopter. But one prisoner in spain tried to use a decidedly more old-school aircraft for his 2009 escape attempt. According to the escape plot, a 4 meter long zeppelin would fly into the prison, deliver him night vision goggles and climbing equipment with which he could scale the prison walls, and the gas-filled vehicle would leave unnoticed. Unfortunately for him, his plan was about as successful as The Hindenburg. A package containing the blimp was intercepted before it could even be inflated, and three accomplices to the escape plot were arrested.

5) Fugitive Dials 911 On Fellow Inmate’s Escape

Never attempt a prison escape unless you are 100% sure that all of your fellow prisoners want to go along with the plan. Otherwise, you might end up like Lester Burns and Michael Coleman after their poorly-planned attempt to break free failed miserably.

Lester and Coleman, along with six other prisoners, were briefly left alone in a prison van while guards were helping an ill inmate get to a hospital. The pair took their chance and broke the partition that separated the back of the van from the driver’s seat. They drove the vehicle about a mile before abandoning it and running away on foot. That’s when Joshua Silverman, one of the hapless prisoners who went along for the ride, decided to distance himself from the two runaways … by calling 911. The first words that he said to the 911 dispatcher were “Uh, yes, ma'am, you're probably not going to believe this…”

Silverman and the rest of the prisoners who remained in the van were picked up shortly afterwards. Lester and Coleman were captured later the same day. Police credit the 911 call in assisting with the quick capture.

6) White Inmate Tries to Impersonate A Black Man

When all else fails, you could always try to give the guards the old switcheroo. Kenneth Burnum plotted to escape from a Hamilton County jail by posing as another inmate who was scheduled to be released. The ruse was going swimmingly until the guards pointed to one small discrepancy. The man that was supposed to be released is black, and Burnum is noticeably white. Burnum was slapped with two criminal charges for the failed escape.

7) Fugitive Posts His Location On Facebook

Social media is undeniably addictive. But there are times when using it just isn’t appropriate. Like for example when you are at a funeral, or a job interview, or if you are trying to run from the law. It’s fair to say that Chris Crego wasn’t abiding by social media etiquette during his brief stint as a fugitive.

Crego was convicted of starting a bar fight and was scheduled for sentencing. But rather than show up, he decided to make his small-time charge much more serious by skipping town. After moving to Terra Haute, Indiana and getting a job at a Tattoo Parlour, he decided to inform his friends of his new whereabouts by updating his Facebook and Myspace pages. Somehow, he didn’t seem to realize that this information could also been seen by law enforcement. The US Marshals captured him shortly afterwards.

8) Man Tries To Punch His Way Out Of The Jail Cell

This is a bad escape strategy for people who are not named Bruce Banner. In 2011, a Florida man (whose non-Bruce Banner name is Hector Luis Campos) decided that the only tools he needed to escape from prison were attached to his wrists.

At about 4 in the morning, prison guards reported hearing banging noises inside Campos’ cell. Upon investigation, they learned that he was punching the brick around the door, even managing to break up some mortar and dispose of it in the toilet. He was stopped before getting very far, and despite the futility of his attempt (and the swollen hand he recieved as a result), he was charged with escape.

9) Inmate Has Accomplice Impersonate US Marshall

Exactly how dumb are prison guards? Evidently, they are smarter than John David Hayes of South Carolina gives them credit for. When the 29-year-old wanted to escape from the Greenville Detention Center, he had a female accomplice call the prison claiming to be a US Marshall. She then claimed that Hayes was scheduled to be let go immediately. When they didn’t believe her, she tried to call in again anyway to try and fool the prison into releasing Hayes. For the failed attempted, Hayes was slapped with additional jail time.

10) Inmate Escapes From Prison … One Day Before Scheduled Release

Most people have enough patience to wait 24 hours before their prison release. Andrew Wilson is not most people. While on a work release program one day before he was set to be let go, Wilson stole a truck and fled in Shelby County, Kentucky. Wilson had served 19 of the 20 days of his sentence for burglary, theft, and unlawful taking and possession of a controlled substance. After the breakout he faced additional theft and escape charges.

11) Handcuffed Prisoners Slam Into Each Other During Escape Attempt

Running away from prison doesn’t require the grace of a ballerina, but it does take enough coordination to escape the police. Two New Zealand prisoners proved that they didn’t have nearly the level of dexterity required to make a respectable escape attempt when they fled a courthouse. The prisoners, who were handcuffed together, caught the chain that linked them on a pole and subsequently collided into each other, causing them both to crumple to the ground. The police nabbed them as they struggled to their feet.

12) Man Dressed As Snoopy Tries To Jailbreak His Friend

When most people imagine a jailbreak, they think of skillful, catlike movements and hiding in the shadows; not a man wearing a cartoon dog costume and waving a firearm. But that is exactly what happened when two men tried to free a friend from a prison in the Isle of Wight. Prison wardens were quite shocked to see a man dressed up as Snoopy from Peanuts attempting to break down a staff door at the penitentiary. Not only was the attempt unsuccessful, but it turned out that the costume-wearing man was at the wrong prison, and his buddy was held elsewhere. The man in the dog costume was eventually subdued and held under the UK’s Mental Health Act.

13) Man Tries To Escape In Luggage

In 2011, Maria del Mar Arjona Rivero visited her boyfriend in a Mexican prison for a one hour conjugal visit. But for some reason, it looked like she was packing for a week-long trip. When she went into his room for a little privacy, she also dragged a large, empty suitcase behind her. And when she walked out, the suitcase was filled… with her contorted boyfriend. She apparently expected to be able to simply walk out of the prison with her packed boyfriend, without anyone noticing. Unsurprisingly, this brilliant escape plan fooled precisely nobody.

DISCLAIMER: It is PROHIBITED by law to use our service or the information it provides to make decisions about consumer credit, employment, insurance, tenant screening, or for any other purpose subject to the Fair Credit Reporting Act, 15 USC 1681 et seq. Instant Checkmate does not provide consumer reports and is not a consumer reporting agency. The information available on our website may not be 100% accurate, complete, or up to date, so do not use this information as a substitute for your own due diligence, especially if you have concerns about a person’s criminal history. Instant Checkmate does not make any representation or warranty about the accuracy of the information available through our website or about the character or integrity of the person about whom you inquire. For more information, please review Instant Checkmate Terms of Use.