Japanese gambler Yoshie Shiratori is the worldwide GOAT of prison escapes—but he sucked at staying out of prison. A professional gambler and thief, Shiratori was first imprisoned in 1936 after being accused of murder and robbery.

Escape one: Shiratori served three years at Aomori prison, then escaped by picking the lock of his handcuffs with a wire he’d taken from a bucket. He was quickly captured and sent to Akita prison with a life sentence.

Escape two: Housed in an “escape proof” cell with bronze walls and only a tiny air vent on the ceiling, Shiratori escaped by somehow climbing the smooth walls of his cell and shimmying out the air vent. Once free, he decided to visit a cop who was kind to him. Do not do this. The cop narced him out and sent him to prison number three: Abashiri prison.

Escape three: Kept in handcuffs and frequently beaten by guards (Japanese prison in the 40s was not a joke), Shiratori assiduously dripped miso soup on his shackles at every meal, until eventually the acid weakened the cuffs enough that he could break them. He then dislocated both of his shoulders and squeezed through the tiny slot where his food was delivered. This time, he stayed out of jail for several years, living in an abandoned mine. But then he killed a farmer while trying to steal a tomato. Shiratori said it was self-defense, but he was sentenced to death.

Escape four: The authorities were really not playing now, and Shiratori was thrown into a specially-designed cell with only a tiny window in the ceiling and watched 24/7 by six armed guards. But the cell-builders were so focused on the ceiling they forgot the floor. Shiratori somehow dug a hole with a wooden bowl and escaped his imminent execution through it. A year later, he was captured, but the court revoked his death sentence and let him serve his life sentence in a Tokyo prison, where he stayed until he was released for good behavior 14 years later. He lived as a free man and a folk hero for the last decade of his life.

Lesson: Never give up.

In 1918, at the height of World War I, British officer E. H. Jones found himself imprisoned at Yozgad, a POW camp in a remote part of Turkey. There was no barbed wire at the camp because it wasn’t needed: The true walls of the prison were the miles of mountains and desert between Yozgad and anything else, and the camp’s policy of enacting revenge on remaining prisoners for escape attempts also dissuaded any would-be Houdinis.

To combat boredom, Jones built a ouija board and quickly found that convincing his fellow prisoners that he could speak to the Spirit World wasn’t difficult, with one exception: C.W. Hill, who happened to have been a stage magician and didn’t buy the act at all. Taking Hill into his confidence, Jones developed a jailhouse mentalism act that eventually drew the attention of the camp’s commandant. Over months, Hill and Jones conned their captors into believing they were in contact with a spirit who knew where a vast treasure was hidden. Eventually they were allowed to leave the prison through the front gates, with passage to the coast, all with the guards’ blessings.

Lesson: Do no underestimate the stupidity (and greed) of your captors.

Today, Alcatraz is a National Historic Landmark that functions as a tourist attraction, but back when it was a running prison, it was a beast—a seemingly inescapable jail on rocky island in the middle of the San Francisco Bay.

Back in 1962, three hardened criminals enacted probably the most famous prison escape in American history and made it off “The Rock.” Whether they made it to freedom or died in the attempt is an open question.

After months of silent preparation, on the night of June 11, 1962, four prisoners placed realistic heads sculpted of toilet paper and paste in their bunks, pulled the grates from the walls of their cells, slipped into the service corridor behind them, climbed a ventilation shaft to the prison roof, climbed down a drainpipe to the ground, scaled two razor-wire fences, traveled to the prison’s searchlight blindspot where they inflated a homemade raft they’d built, and paddled out into San Francisco Bay, never to be seen again.

The guards didn’t notice they were gone until the morning—the plaster heads bought them time—and after an extensive search in which the remains of their rafts and life jackets were found, the FBI concluded that the men most likely drowned. But family members of the escapees reported getting letters and postcards from them for years, and there were numerous other semi-credible but non-confirmed sightings of the men in the decades after their escape.

Lesson: You can’t overestimate the importance of planning ahead.

On January 21, 1970, Harvard-psychologist-turned-LSD-evangelist Timothy Leary was sentenced to twenty years in jail for marijuana possession. (The government was trying to make a point—they hated his outspoken advocacy of LSD use.) Upon reporting to prison, Leary was given a series of psychological tests to determine what kind of prisoner he was likely to be, as well as the kind of prison work he was suited to. But while at Harvard, he had actually developed and written some of those tests, so he knew exactly how to answer to come off as a conforming, conventional person with a great interest in gardening and none in escape.

Leary was assigned to be a gardener in a low-security prison, and he soon escaped by climbing a fence. Once outside the prison, he was met by members of the extremist political group Weather Underground, who smuggled Leary and his wife to Algeria. They then moved to Switzerland. An ill-advised trip to Afghanistan ended in Leary’s extradition to the US, though, where he was sent to Folsom prison with an extra five years tacked on to his sentence for his escape.

Leary wasn’t done yet though—over the next few years he enacted a different kind of plan to gain his freedom: Become a snitch. Leary became an FBI informant, supposedly even dropping a dime on the Weather Underground, and was sprung in 1976 partly in exchange for his cooperation with authorities.

Lesson: Some friends will rat you out.

Originally built in In 1046, Colditz Castle is an imposing structure near Leipzig, Germany. During World War II, the building was converted into a high-security prisoner-of-war camp for officers deemed security or escape risks. The castle was meant to be escape proof, but during the five years it was in operation, there were 174 documented escape attempts and 32 were successful. POWs dug tunnels, made ropes out of sheets, climbed the fences, dressed up as women, hid in the well, escaped through the Kommandant’s office, feigned insanity, and more. But the most audacious escape attempt was the “Colditz Cock.”

The brainchild of British Lieutenant Tony Rolt, the Colditz Cock was a full-size glider that 13 of the camp’s POWs assembled in secret in the attic of Colditz’s chapel. They’d copied the plans from a book on aeronautics from the prison library, and the glider was constructed from bed slats and spare wood behind a false wall that the POWs constructed. They even rigged an electric alarm system to alert them if guards were coming near. When completed, the Cock had a 32-foot wingspan and was 19 feet long from nose to tail.

Sadly (or happily), the glider never flew. As it was nearing completion, the camp was liberated by the allied army. Although the original was never tested, a replica of the Cock based on the original design was test flown successfully in 2000, with members of the original construction crew looking on.

Lesson: Fortune favors the bold.

Convicted murderer Richard Lee McNair escaped a lot. In 1988, shortly after being arrested and charged with two counts of attempted murder and a robbery, McNair bolted from the police station. He was recaptured a few hours later. McNair then slipped his handcuffs and ran again, only to be re-recaptured after a short chase. After he was sentenced to a double-life sentence plus 30 years, McNair escaped from the North Dakota State Penitentiary by slipping through an air duct. After ten months of freedom, McNair was re-recaptured and eventually sent to a maximum security prison in Pollock, Louisiana, where he stayed until 2006.

McNair worked repairing damaged mail bags that were then loaded onto a pallet, shrink-wrapped, and taken out of the prison by forklift. It gave him a mad idea: McNair spent months building an “escape pod,” complete with air hose, that he put under the mailbags and crawled into. He was forklifted out of the secure area of the prison, cut himself free, and walked. After nearly two years of freedom, McNair was re-re-recaptured in Canada and extradited back to the US. He’s now held in a Supermax prison in Florence, CO, presumably plotting his escape.

The lesson: Think outside the box.

Unlike most of the escapees on this list, political activist and Black Liberation Army member Assata Shakur (the step-aunt and godmother of Tupac Shakur) managed to stay out of prison after her daring escape.

Convicted of first-degree murder after a shootout with a New Jersey state troopers in 1973, Shakur was remanded to the Clinton Correctional Facility for Women in New Jersey. She was there until 1979, when her friends in the BLA broke her out. The activists showed up as visitors, then drew guns and a stick of dynamite. They held a couple guards hostage long enough to commandeer a van, which they used to drive Shakur away.

A massive hunt failed, mainly because no one talked to the cops, and Shakur wasn’t spotted in public again until 1987 when she gave an interview to Newsday from her home in Cuba. She lives in Cuba to this day, despite numerous extradition attempts and a two million dollar reward for her capture. Donald Trump even name-dropped her personally when he was president, but was unable to lock her up.

Lesson: Keep close and trustworthy friends.

The 30-year Irish ethno-national conflict dubbed “The Troubles” was heavier on grueling attrition and bombings than heroism, but The Mountjoy Prison helicopter escape is a shining exception. After being imprisoned without trial, Irish Republican Army Chief of Staff Seamus Twomey and two other senior members of the IRA found themselves imprisoned at The Mountjoy Prison in Dublin, Ireland. On Halloween 1973, their boys busted them out.

IRA soldiers hired a commercial helicopter. When it arrived, they held the pilot at gunpoint and ordered him to fly to the prison and land in the middle of the exercise yard. While the other prisoners held the guards back, the IRA leadership stepped into the helicopter and flew to freedom. The whole operation was over in less than a minute. Nothing blew up, no one was hurt, and the Wolf Tones wrote a song about it—a banger if you like Irish folk rebel music.

Lesson: Have a helicopter waiting.