How Hollywood Made Prison Breaks Seem Heroic

Movies and television have made jailbreaks seem like the ultimate victory against a corrupt system, but the reality is far less heartwarming.

Columbia Pictures

The details of the Mexican drug lord Joaquín Guzmán Loera’s escape from prison on July 11 are pure cinema. He fled through a two-foot by two-foot hole drilled in the shower area of his cell, climbing down a ladder to a mile-long tunnel, complete with lighting, ventilation, and a motorcycle on rails. Much like the June breakout of two inmates from the Clinton Correctional Facility in Upstate New York, the news of Loera’s escape was both frightening to nearby citizens and a political setback for local officials. But its vivid details—the tunnel dug just high enough for its subject to walk through, the surveillance camera that had just one blind spot, the whiffs of larger corruption—couldn’t help but conjure memories of one of Hollywood’s favorite subgenres: the escape caper.

The Internet was quickly flooded with pop culture’s most indelible (one might even say clichéd) imagery of prison breaks. A torn-down movie poster revealing an escape route in The Shawshank Redemption. Paul Newman throwing chili powder behind him to mask his scent in Cool Hand Luke. An ensemble cast of anti-heroes scattering into the woods on the TV show Prison Break, a one-time hit series that Fox is now reportedly planning to revive.

Considering that jails are essentially supposed to keep criminals out of society, it’s notable how much glee audiences derive from watching someone bypass the protections of a maximum-security prison. But that’s where fact and fiction begin to deviate. Movies and television have long used jailbreak as a thrilling and dramatically potent plot device, but typically affirm the breakees as misunderstood heroes in the process—people who’ve been unfairly convicted or who are Robin Hood-type criminals who largely eschew violence. The redemptive format of the genre belies the reality, even while fictional escapes and real-life escapes continue to inspire each other.

Loera, nicknamed “El Chapo” (or “the shorty”), is one of the world’s most notorious drug traffickers, as well as one of the richest, and at the time of his arrest in 2014, had imported more drugs (including cocaine, heroin and methamphetamine) to the United States than anyone in history. A security analyst called him “the jewel of the crown,” and his escape was seen as a devastating blow to the Mexican government. The two men who broke out of Clinton, Richard Matt and David Sweat, were hardened felons serving time for murder and whose getaways put nearby communities on high alert.

It’s far rarer for a Hollywood jailbreak to feature such unsympathetic protagonists. Usually, to engineer a daring dash out of prison, one needs to possess both incredible craftiness and a winning personality, as well as be either falsely accused or extremely repentant. Andy Dufresne (Tim Robbins) chisels his way out of Shawshank State Penitentiary after serving 17 years of a wrongful conviction; his friend Red (Morgan Freeman) is only freed when he bluntly discusses his inescapable guilt to a parole board. Luke Jackson (Paul Newman), an angry war veteran, is thrown in the slammer for a victimless bit of vandalism in Cool Hand Luke; the heroes of The Great Escape are breaking out of Nazi imprisonment; the cast of Prison Break are pawns in a larger game of corrupt political gamesmanship that goes all the way up to the White House.

If the hero is an active criminal, he usually abides by a code of honor, like Clint Eastwood’s bank-robber protagonist in Escape from Alcatraz, who defines himself in opposition to the gangsters and rapists who reign in the notorious prison. The same goes for Jack Foley (George Clooney) in Out of Sight, who robs from the rich but is nonviolent. Escaping from jail is just another of his sexy jaunts in the Steven Soderbergh film, which is driven by the amorous frisson between Foley and the U.S. Marshal Karen Sisco (Jennifer Lopez), whom he runs into during his getaway. The titular protagonist of Steve McQueen’s Papillon is a safecracker wrongly accused of a far worse crime, and the two-and-a-half-hour epic is an existential critique of the Kafkaesque horror of prison that features long, torturous spells in solitary confinement.

The prison-drama narrative usually follows a rigid form for a reason. Most moviegoers have little experience of life behind bars, says Frankie Y. Bailey, a criminal justice professor at the University at Albany. “A lot of what they're learning comes from movies or television.”

The protagonist is almost always a new inmate, often wrongly accused, who’s shown the ropes by a wiser, older friend. He or she is defined in opposition to villainous wardens or correctional officers who represent a general oppressive sense of injustice for the audience to rebel against. In that framework, any attempt at freedom feels justified and hard-earned—and usually involves a mix of personal charm and MacGyver-like ingenuity. “It’s like going to a gangster movie or a horror movie. You can play with those stereotypes, but an audience does go in with certain expectations,” Bailey says.

Referencing the Clinton breakout, she notes the soapy drama behind the details of Matt and Sweat’s escape—a female staffer has been arraigned on charges of aiding them, and allegedly participated as part of a larger plan to kill her husband that she backed out of. “At some point it's going to be a Lifetime movie, because that’s the kind of story it is. But [the prisoners] don't fit into the Hollywood stereotype of people you want to root for,” Bailey says.

Instead, Hollywood seeks out prison stories with a redeeming edge, or some social value. Realism is sacrificed partially because of a lack of access to the world inside bars. “Once prisoners are behind walls, particularly in maximum-security prisons, they're inaccessible,” she says. “That's one of the reasons we get a lot of stereotyping and a lot of reasons why the media has to rush to stereotype to fill in the gaps. It blurs the line between news media and entertainment ... You don’t see the everyday, normal life behind bars.”

Exceptions often end up proving the rule, like Netflix’s Orange is the New Black, which itself has featured multiple escape plotlines (that all seem to end in death, one way or another) among its more prosaic stories of life in prison. Inspired by Piper Kerman’s autobiography, the series is shown through the eyes of a white, middle-class protagonist, who gets a whole new perspective on a world she barely understood before her conviction.

Just as the media rushes to romanticize any escape from freedom, pop-culture representations of prison can even make life behind bars seem alluring to some. Many states are now moving away from having inmates wear orange jumpsuits as a result—which themselves were designed in the early 20th century to remove the stigma of the black-and-white stripes Hollywood had made so familiar.

“They’re becoming too popular,” Bailey says. “The uniform itself, there are periods where it moves into fashion. A few years ago in New Orleans, I saw an orange jumpsuit on sale at a gift shop in the French Quarter.”

And yet movies and TV have become a cultural prism through which the public can grasp the grim realities usually beyond their reach. After the Clinton jail break, New York Governor Andrew Cuomo led reporters on a tour of the prison to navigate just how the inmates had broken out. “They put dummies in the bed,” he told the press, indicating how Matt and Sweat had found time to execute their plan. “Like in The Shawshank Redemption.