5) Seduction and Spiked Whisky in Brazil

In a startling display of incompetence, guards in a small city in western Brazil allowed two women dressed as "sexy" police officers inside a prison. The women reportedly spiked the guards' whisky, took their keys, and let at least 26 inmates leave with weapons and ammunition.

The next morning, police found the guards handcuffed with little memory of what had happened. "One was found dizzy, trying to wake up. Another slept for the whole afternoon, and couldn't even be questioned," a police official stated, according to Latina magazine. 

Police believe the escape was orchestrated by an 18-year-old prisoner and his girlfriend.

4) Daring Helicopter Escape in Chile

Four inmates escaped from a Santiago high-security prison in 1996 via helicopter. The prisoners were in an open-air recreation space when a helicopter dropped a metal basket into the prison to rescue five leaders of the Manuel Rodriguez Patriotic Front, a group that fought against Chile's dictatorship and remained active after the country's transition to democracy. Guards shot at the helicopter, and during the commotion one of the five fell off the basket, according to El Pais.

The organization had a history of escape attempts: six years earlier, 48 members of the rebel group and another guerrilla fighter dug a tunnel from a prison in Santiago to an abandoned railway station, which -- according to police sources cited by the Los Angeles Times -- was "a real work of engineering."

3) Walking Out of Mexican Fortress Dressed in Drag

After he was caught smuggling cocaine through an airport in Mexico in 1973, US citizen Dwight Worker was sentenced to five years in Lecumberri Prison, a notoriously impenetrable fortress. Worker was the second person ever to escape from Lecumberri; the first was Pancho Villa, one of the leaders of the Mexican Revolution.

Worker fell in love with an American woman who was visiting another inmate, and together they devised a strategy to smuggle female clothing, a wig, and makeup into the prison. Worker then walked out of Lecumberri dressed as a female visitor with a forged pass. He caught a bus and a train to the US border and later married the woman who helped him escape.  

2) Debunking El Chapo's Famous Escape in Mexico

In what is perhaps the most famous escape in Mexican history, Sinaloa Cartel leader Joaquin "El Chapo" Guzman allegedly snuck out of a maximum security prison in 2001. 

The Mexican government said El Chapo was shuttled out of the prison hidden in a laundry cart, but others have questioned the official narrative and argued that instead of a daring tale of escape, El Chapo's story is one of official corruption.

Investigative journalist Anabel Hernandez wrote in her book Narcoland that the prison's sophisticated heat sensors would have immediately detected a body in the laundry cart. Instead, Hernandez found evidence that federal police walked El Chapo out of the prison dressed as a member of their SWAT team. Another journalist who interviewed one of the drug lord's accomplices corroborated this version of events.

El Chapo frustrated authorities for years, maintaining elaborate systems to prevent any future arrest. One security expert called him "the king of tunnels and drains," according to The Economist. Indeed, El Chapo once evaded police by escaping through a trap door under his bathtub. He was finally recaptured in 2014.

1) Pablo Escobar's Escape From Luxury Prison

In 1992, notorious drug lord Pablo Escobar escaped from a prison he had designed for himself. Named "The Cathedral," Escobar's private prison sported a chapel, a soccer field, a discotheque, and handpicked guards.

After he allegedly ordered the torture and killing of four of his lieutenants at the compound, authorities decided to transfer Escobar to a military jail and sent two officials to the prison to inform him of the change. After Escobar's men threatened the officials, Colombian soldiers arrived on the scene, provoking a hasty retreat by Escobar and his guards. A massive manhunt followed, and Escobar went on the lam for 17 months until he was killed in a shootout on a Medellin rooftop.