28 Funny Times a Small Amount of Power Went to Someone’s Head

22 TV Shows That Lasted Way Longer Than They Should Have

50 Deliciously Funny Tweets About Food, Served Hot and Fresh

Is Bill Burr the Lost Member of Smashing Pumpkins?

10 of the Absolute Worst Movies to Watch With Your Parents While You’re Home for the Holidays

29 Harrowing Tales of Real-Life Prison Escapes

The answer is clear: We need more prisons

29 Harrowing Tales of Real-Life Prison Escapes

March 22, 2024

In honor Alabama’s newly-announced $1 billion prison, let’s celebrate some scoundrels who told Johnny Law to go eat shit.

Click right here to get the best of Cracked sent to your inbox.

29

PRISON ESCAPES DIGGING YOUR WAY OUT. In 1990, left-wing guerrillas who fought Pinochet's dictatorship dug a tunnel out of a Chilean prison. How many, you ask? Three? Five? Nope. 49 people escaped after tunneling through 240 feet and coming up in an abandoned railway station. And if it sounds like a movie, it was already made: 2020's Jailbreak Pact. CRACKED.COM — Source

28

PRISON ESCAPES THE ESCAPE FROM ALCATRAZ (AS SEEN IN ESCAPE FROM ALCATRAZ) Alcatraz was deemed impossible to escape. In 1962, however, three people climbed out air ducts they spent six months widening. The truly insane part, though, is that they disappeared into the night in a makeshift rubber raft, wearing life preservers made out of raincoats - after stuffing their beds with decoy papier- mâché doubles. Yes, exactly like in teen movies. CRACKED.COM — Source

27

PRISON ESCAPES MISO SOUP AND DISLOCATED SHOULDERS. Yoshie Shiratori escaped from prison four times. Dude is a legend in Japan. For his third break in 1944, he spit soup on the handcuffs and food slot, which eventually became corroded and allowed him to wiggle through by dislocating his shoulders. Не then lived deep in the mountains for two years, until getting caught yet again. CRACKED.COM — Source

26

PRISON ESCAPES CHARLES THOMPSON JUST WALKED OUT. Thompson smuggled in civilian clothes, quickly changed after a meeting with his lawyers, and walked out. It gets dumber: When he was stopped by the front desk guard, he just flashed his inmate badge - and then, to repeat once again, he just walked out. CRACKED.COM — Source

25

PRISON ESCAPES RICHARD LEE McNAIR MAILED HIMSELF OUT. McNair escaped three jails, so the man clearly had a passion for the craft. In 2006, while held in a maximum-security prison, he got a job repairing mailbags, and built an escape pod with a breathing tube. Then he got in, waited until it was covered with mailbags, and mailed himself out tucked inside the shrink-wrapped mailbag pallet. Sounds cozy. CRACKED.COM — Source

24

PRISON ESCAPES NEIL MOORE TURNED HIMSELF IN BECAUSE ESCAPING WAS TOO EASY. Instead of asking his jailers for cigarettes or porn, Moore got a smartphone. With it he made a fake version of the County Court website, and mailed the prison freeing himself. Days later he turned himself in (because the man needed a challenge, we assume). CRACKED.COM

23

PRISON ESCAPES THEY PASSED PEACHES OFF AS GRENADES, YOU GUYS. Nadine had been learning how to fly helicopters for six months. Her husband was a petty bank robber called Michel Vaujour, and he had painted nectarines as grenades, as one does while jailed. Vaujour used his weapons to get access to the roof and climb up the cable Nadine dropped down from the chopper. CRACKED.COM — Source

22

PRISON ESCAPES KROPOTKIN WAS AWESOME (ALSO, НЕ ESCAPED PRISON). Helped by his friends, anarchist Peter Kropotkin escaped prison in 1876 in an elaborate, Ocean's Eleven- like plan (that's mutual aid, y'all). At the climactic moment, he made a run for it through an open gate. After a shave, the gang celebrated at St. Petersburg's fanciest restaurant (because no one would look for an anarchist there), and he then fled to London. CRACKED.COM — Source

21

PRISON ESCAPES JOHN MANARD ESCAPED IN A DOG KENNEL. Toby Young would take dogs to a Kansas prison to get them trained and allow the inmates to care for them. Lovely idea. But she also fell in love with John Manard, and in 2006, helped him escape inside a big dog kennel. Less lovely idea. CRACKED.COM — Source

20

PRISON ESCAPES THE GREEK ROBIN HOOD CAUGHT A CHOPPER. TWICE. Vassilis Palaiokostas, something of a Greek version of Robin Hood, was sentenced to jail in 2000 - and then simply took the escape helicopter that landed in the prison exercise yard out like it was a cab. And he did this twice. They arrested him again, and he repeated the feat in 2009, because why fix what ain't broke. CRACKED.COM — Source

19

PRISON ESCAPES WAIT, IS THAT A HELICOPTER? Helicopter prison breaks are so common they have their own Wikipedia page, but the 1973 IRA escape is a classic. An IRA member hijacked a chopper, landed in the yard of a Dublin prison, and three other members climbed in. Embarrassingly, the slack-jawed guards did nothing because they thought it was a random visit by the new Minister of Defense. ZALQU CRACKED.COM — Source

18

PRISON ESCAPES DILLINGER ESCAPED VIA THE POWER OF ART. In 1934, John yes, that John Dillinger Dillinger was held in the supposedly escape-proof county jail of Crown Point, Indiana. But the jail wasn't equipped against, erm, somewhat talented wood carvers, because Dillinger whittled himself a fake gun that allowed him to threaten the guards enough to get real guns - and make a run for it. Truly a master craftsman. CRACKED.COM — Source

17

PRISON ESCAPES OUTSOURCED LUXURY PRISON BREAK Drug kingpin Joaquín El Chapo Guzmán got to spend one of his jail stays chugging boner pills with sex workers, so of course his prison break was classy. Through sheer power and influence, he outsourced a mile-long tunnel complete with artificial light, air ducts, high-quality construction materials, and a friggin' motorcycle. What a legend. CRACKED.COM — Source

16

PRISON ESCAPES CASANOVA: MASTER SEDUCER AND PRISON BREAKER. While in a Venetian prison in 1755, Casanova sent an iron spike to another cellmate, who used it to escape through his roof and dig a hole on Casanova's. Then they climbed out to the building's roof, entered again, slept, changed into fancy clothes, and walked out through the front door. CRACKED.COM — Source

15

PRISON ESCAPES TED BUNDY LAWYERED HIS WAY TO FREEDOM. In 1977, Bundy waived his right to an attorney and decided to represent himself. In what otherwise sounds like a wacky Adam Sandler comedy, however, he used the freedom to move around the courtroom (you know, being his own lawyer) to brush up on his law in the library - where he simply escaped through a window. CRACKED.COM — Source

14

Sean Sykes, Jr. got out of an interrogation because his farts were too mighty for the detective to handle. After being found in a car with a backpack that had drugs and guns in it, he was brought in for an interrogation. When he stopped answering questions with anything other than farts, the interrogation was ended, and he wasn't charged with anything at that time. CRACKED.COM — Source

13

The Royal Canadian Mounted Police were closing in on notorious child molester Ernest Fenwick MacIntosh, so they called him and left a message. MacIntosh immediately fled the country. Не was finally caught and convicted seven years later for molesting a 9-year-old boy in Nepal. CRACKED.COM — Source

12

A criminal labeled as 'dangerous' got released after his accomplices sent a false document demanding his release using a fax machine in a grocery store. Not only did the document contain spelling errors, it also had the mark of the grocery store which the officials actually saw. They claimed that spelling errors were actually quite common in court documents and checking the document's source was not a part of the procedure. CRACKED.COM — Source

11

In June 1977 Ted Bundy served as his own defence lawyer in a murder case against him. Не was allowed to walk without handcuffs or shackles. Не was also allowed to use the law library and this is where he escaped from. When the guard went for a smoke, he escaped from the 2nd floor window. GRACKED.COM — Source

10

Some Liverpool police officers literally let Craig Clamp - who was under arrest - walk away from the hospital without a hassle. - ONE Не was taken there under supervision after having a heroin episode but when the time came to switch shifts, the new officers watched the wrong patient. The next time they saw Clamp, it was in the CCTV footage of his getaway. CRACKED COM — Source

9

Wanted hacker Kevin Mitnick stayed a fugitive from the FBI for two and a half years... CRACKED.COM partly because FBI agents made regular phone calls, and he used their call logs to track their movements. — Source

8

Jhon Gutiérrez Rincón and Olmedo Vargas escaped from a maximum security prison in Columbia by getting one of the guards drunk. 1.00 INPEC INPEC INI EPAMSCAS BOGOTA EPAMSCAS ERON BOGOTA 0113046 120 TD 113061306 SCAS N BIOKO D SEPTIFMARE DF2017 01 DICIEMBRE 2017 13046120 TD1130613 After sharing drinks with him, the inmates managed to соах the intoxicated guard into letting them out on a booze run, and run, they did. Booze? Not SO much. CRACKED.COM — Source

7

29 Harrowing Tales of Real-Life Prison Escapes — Source

6

CRACKED.COM Kevin Jerome Pullum escaped prison using Eddie Murphy's picture Не had an elaborate escape plan, but for that, he needed a picture for his fake ID. With limited choices, Pullum chose the picture he considered most resembled him: that of Eddie Murphy. The plan succeeded and he nonchalantly walked out of prison, which wouldn't have happened if a guard just took a quick look at his ID and saw Dr. Dolittle's face. — Source

5

James Muth (who was arrested for assault with his bail set at $50,000) fled after he was mistakenly freed from the Boyd County jail in Kentucky. While acting upon an alert for his release that was issued in a different county, the Boyd County officials didn't think to verify his local criminal status (as per the usual protocol). To make matters worse, they realized their mistake but didn't notify the local police. CRACKED COM — Source

4

CRACKED COM Paul Bernardo was free to rape four girls and kill two others because the police somehow overlooked testing his DNA. Due to a link with rape cases, police had obtained his DNA sample as early as December 1990 but due to a coordination problem, the testing was never carried out. Even when the police realized that Bernardo lied about the circumstances of his sister-in-law's brutal rape and murder, they never pressed him further. Не was immediately arrested when the DNA test was finally carried out in February 1993. — Source

3

CRACKED.COM During a manhunt for Christopher Dorner, a former police officer who went on a killing spree after he was fired, the LAPD shot up two different vehicles that were in no way similar to Dorner's. Two innocents were wounded in the process,and neither of them looked anything like Domer. The manhunt only ended ten days later when Dorner decided to shoot himself while being surrounded by the LAPD. I - 8068341 — Source

2

Serial killer Richard Ramirez, the Night Stalker, was once pulled over by a police officer when he was speeding away from a crime scene in a stolen car. MON-FRI The officer asked Ramirez whether he was the suspect in the recent string of rapes and murders. Ramirez responded, No way, man. The officer took his word for it, even though both the man and the vehicle matched descriptions that had been put out. Не then walked away from the vehicle, and Ramirez used the opportunity to make a run for it. CRACKED COM — Source

1

It was local due diligence and sheer luck that put Charles Manson and his family behind bars. A 10-year-old boy found the gun The police used in the Tate murders, and a missed vital КАВС News TV crew found the clothes the killers discarded. clues. One of Manson's followers, Susan The police Atkins, had been arrested on a lucked into different charge, and went on to tell a fellow inmate all about the a witness. murders the cult committed. CRACKED.COM — Source

Tags:

Visual

Scroll down for the next article

Must Read

Trivia & Jokes

35 Funny Bits of Family Drama People Have Dealt With on Thanksgiving

Science & History

In the Interest of (Literal) Poor Taste, Here’s A Collection of Hilarious Turkey Cooking Disasters

Science & History

5 Family Dinners That Turned Deadly

Movies & TV

What Would Ongo Gablogian Say About These Ugly ‘It’s Always Sunny in Philadelphia’ Funko Pop Trading Cards?

Trivia & Jokes

40 Fun Facts About Feuds and Fights, Both Fake and Non-Fiction

Movies & TV

This Is the Only Time That Siskel and Ebert Reviewed a TV Comedy

VIRAL ON CRACKED

1

19 Photos That Look Like Time Travel

2

29 Facts About Money That Seem Made Up (But Aren’t)

3

23 Eyebrow-Arching Backstories Behind Musician Stage Names

4

22 TV Shows That Lasted Way Longer Than They Should Have

5

Five of the Most Expensive Toys in the World