On April 25, over the course of 4½ wee morning hours, more than 480 imprisoned Taliban insurgents and other inmates made their way through an underground tunnel to freedom. The passage, which stretched for 1,050 feet (320 m), bypassed government checkpoints and watchtowers, barriers and razor wire that stood between the prisoners (including some 100 Taliban commanders) and the night. At 4 a.m., guards at Sarposa prison in Kandahar City (the former Taliban capital) discovered the jailbreak — just 30 minutes after the Taliban said they had gotten all the inmates safely to a house at the other side of the tunnel. The convenient timing, along with the fact that the inmates somehow escaped from locked cells in the dead of night and that guards had not noticed five months' worth of tunnel drilling, aided suspicion that the inmates had help from guards or officials, or both. This extraordinary break was not even the first such feat by the Taliban. At the same prison in 2008, a coordinated attack by insurgents freed some 900 prisoners.
2. The Escape from Alcatraz
Alcatraz was supposed to be America's only escape-proof prison. Which is why, nearly 50 years after three men vanished from inside its walls on June 12, 1962, the act still fascinates. The Rock, an island set in the middle of San Francisco Bay, held the worst of the worst, including Frank Morris and John and Clarence Anglin (who were all serving life sentences for robbery, among other crimes). The men allegedly dug through the concrete fortress using a metal spoon (strengthened with silver from a dime) and an improvised drill crafted from a stolen vacuum cleaner. Adding to the intrigue, they smartly muffled the sound of their drilling with accordions played during music hour and left behind papier-mâché dummies — whose heads they topped with hair stolen from the prison barber shop — in their place. Though the prison claimed the men drowned at sea (which would thus maintain the belief that the penitentiary had no successful escapees in its 29 years of operation), their remains have never been found and the U.S. Marshal Service maintains an active case file on the trio. The break was the basis for the 1979 movie Escape from Alcatraz, starring Clint Eastwood.
3. The Great Escape
The Great Escape, as it is known, was an attempt by Allied prisoners of war to escape Stalag Luft III, a Nazi maximum-security work camp, in the latter half of World War II. From April 1943 to March 1944, over 600 prisoners worked on the project. They dug three tunnels, nicknamed Tom (which was hidden in a dark corner), Dick (underneath a bathroom drain) and Harry (behind a stove), which they hoped would deliver them to freedom. The tunnels were positioned 30 feet (9 m) underground to escape detection by the guards. TIME described them in 1963 as, "a marvel of Swiss Family Robinson ingenuity." The plan, concocted by a British officer named Roger Bushell, also provided the expected 200 escapees with forged papers that would help them evade recapture once they were free. Of the three tunnels, only Harry was completed. Two hundred men tried to escape out of it on March 24, 1944, only to discover that it was too short; when exiting the tunnel, the prisoners found themselves completely visible and near a guard tower. Because of this and several other setbacks (including an air raid), only 76 men made it out of the tunnel that night. All but three were recaptured. Of those, 50 were shot by the Gestapo. Despite the plan's failure, it was bold enough to merit a 1963 movie starring Steve McQueen.
4. Imrali Island and the Midnight Express
In 1970, Billy Hayes, a 23-year-old New York student, was caught attempting to smuggle hashish out of Turkey. He was sentenced to just over four years in prison and was eventually transferred to Imrali Island in the Bosphorus Strait. When his sentence was weeks from ending, Hayes received an extended sentence of 30 years. Refusing to spend the rest of his life in prison, Hayes, who was given a job on the docks, escaped in a rowboat in 1975. He made his way to Istanbul and, when he could not secure a hideout, dyed his hair and made his way to Greece, where he was eventually deported to the U.S. In 1977, Hayes wrote the book Midnight Express about his ordeal. When it was made into a film by Oliver Stone (screenplay) and Alan Parker (director), the story was altered, including what Hayes says are scenes of violence and rape that never occurred. In a 2007 interview, Hayes said, "My problem with the movie is there are no good Turks in it." The film went on to win two Academy Awards, including Best Screenplay.
5. The Maze
The Maze, located about 10 miles (16 km) west of Belfast, opened in 1971 and housed many of the most notorious offenders during the Troubles. There were several escape attempts from the maximum-security prison before it was closed in 2000. But a 1983 breakout by 38 IRA prisoners was the biggest event in the history of the Maze, once considered one of the most escape-proof prisons in Europe. With guns smuggled into the prison, the escapees, led by Bobby Storey and Gerry Kelly, took over H-Block 7, killing one guard and wounding several others. When a van delivering food supplies arrived, the men took the passengers hostage and used the vehicle to escape. Within a few days of the break, 19 prisoners were apprehended (including Storey, who received an additional seven years for his participation). The remaining 19 were shuttled to safe houses and some were sent to the U.S and other countries (a few died or were killed while on the lam). Kelly and Brendan McFarlane, another escape leader, were eventually returned to the prison after being extradited from Amsterdam.
6. John Dillinger
"I know he's a bad baby and a jailbreaker but I can handle him," Sheriff Lillian Holley said of John Dillinger, according to a 1934 issue of TIME. The notorious gangster had been taken to Indiana, where he was wanted for killing a policeman, following his capture in Arizona in January of that year. Only months earlier, his cohorts had helped him break out of an Ohio jail where he had been serving time for bank robbery. Yet contrary to the authorities' boasts, the Crown Point, Ind., jail was as escape-proof as the Titanic was unsinkable. On March 3, 1934, Dillinger, the FBI recounts, used "what he claimed later was a wooden gun he had whittled" to break out. And he imprisoned guards before driving away — in the sheriff's car. "If I ever see John Dillinger," Holley was also quoted as saying, "I'll shoot him dead with my own pistol. This is too ridiculous to talk about." In July that same year, after an intense manhunt, Dillinger was shot dead, outside the Biograph theater in Chicago.
7. The Libby Prison Escape
Under the cover of darkness in 1864, more than 100 Union soldiers broke out of Libby Prison in the heart of the Confederacy in Richmond, Va. A group of northern soldiers inside the prison found a way to dig a tunnel from the prison basement that let out beyond its walls. The basement was so infested with vermin they called it "Rat hell." But after a couple of weeks of burrowing, they surfaced inside a tobacco shed. One hundred and nine Union soldiers eventually escaped. Though many were recaptured and a few died in their attempt to make it back north, it remains the largest prison escape of the Civil War.
8. Pascal Payet, the Crafty Frenchman
This Frenchman has a knack for Hollywood-style escapes. In 2001, he fled a French prison via helicopter. In 2003, he again used a chopper to help three others escape the same facility. After he was recaptured, Payet escaped yet again in an even more dramatic jailbreak. A copter was hijacked in Cannes and flown to a state penitentiary in Grasse, where it landed on the prison's roof. Three men jumped out with pistols and sawed-off shotguns, busted their way in and came out with Payet. That unleashed a massive search for the men, and three months later Payet was caught in Spain. It's unclear whether he's got another dramatic escape in him.
9. John Gerard and the Tower of London
Inmates in the Tower of London may not have had to worry about advanced security technology when plotting their escapes, but then, not many prisoners today have to deal with crossing moats. The 1597 jailbreak of John Gerard, a Jesuit priest imprisoned and tortured under Queen Elizabeth I's Protestant reign, involved orange-juice invisible ink, string, rope, a boat, a little help from his friends and, as Gerard would have it, a lot of help from God.
10.Napoleon Leaves Elba
By the spring of 1814, the armies of France's continent-conquering Napoleon were a bedraggled mess, reeling from a disastrous campaign in the Russian winter. Surrounded and weakened, Napoleon was forced to abdicate his imperial throne and sent into exile on the tiny Mediterranean island of Elba. Now, you can say it's hardly a prison when you get to claim sovereignty over a whole island, keep a small navy and spend your days surveying land and ordering the construction of iron mines, but Napoleon knew his enemies would not tolerate his presence in Elba long and had plans to send him much further to St. Helena in the Atlantic. So Napoleon stealthily abandoned Elba with a small force and landed on French soil — in a famous encounter, the French regiment sent to intercept the Emperor on the run simply joined ranks with him. And soon the entire nation would rally around him once more. But in the summer of 1815 his luck ran out and his armies were defeated decisively at the famous battle of Waterloo. Napoleon was banished to St. Helena, a prison from which this time there was no escape.