Solo: A Star Wars Story is about a young man lured into a life of smuggling and thievery. Deadpool 2 stars an actual murderer. Why do we admire heroes who commit crimes? On the latest episode of That Looks Familiar, Beth Elderkin shares the stories of real-life “Lovable Rogues” from history and looks at what happens when true stories of convicted criminals are changed from tragedies into victories.
A Lovable Rogue is a heroic character who’s known for breaking the law, but we love them anyway—not in spite of their crimes, but because of them. It’s usually because they’re attractive, charming, clever, generous to the poor, or some kind of combination. It’s usually best if they’re not known for killing people (outside of self-defense), but as we’ve seen with Deadpool that can be finagled a bit.
Besides characters like Han Solo and Deadpool, there are a few notable “Lovable Rogues” scattered throughout history. For the most part, Lovable Rogues are created in hindsight, with stories of real-life criminals becoming romanticized or even fictionalized years after they happened. But sometimes, these so-called rogues are beloved within their communities during their lifetimes.
There’s Harm Peery, the thrice-elected “Cowboy Mayor” of Ogden, Utah. During the 1920s and 1930s, at a time of Prohibition and moral pearl-clutching, Peery was a total renegade. He accumulated countless tickets and arrests over things like speeding and gambling violations at his bar, but the people loved him! Seemed he could do no wrong, even though he did a lot of wrong stuff. Like one time, as mayor, Peery smashed open a cigarette machine at City Hall so the city engineer could get some smokes. A journalist tried to take photos of the damage (unethically altering the crime scene while doing so), leading Perry to chase him down and threaten him... along with anyone else who tried to do the same. He got arrested for that, a couple of times.
Then, there’s the story of Half-Hung MacNaghten, a man from the 1800s who accidentally killed his girlfriend while trying to kidnap her. He was caught and sentenced to death by hanging. However, folks saw him as this tragic romantic hero and didn’t want to see him die. Luckily, he didn’t—at least not at first. When the noose man first tried to hang him, it didn’t work. John MacNaghten survived! The crowd saw this as a sign that God wanted him to live and begged for his release. Instead, he was rehung. But his legend has gone down in Irish history—there’s even a folk song about him.
Not even close! But we were fascinated by them. Following the expiration of Britain’s Licensing Act in 1695, which had prohibited anyone from making stuff on printing presses without government approval, we got a slew of new published works throughout Europe. This led to the rise of the criminal biography, collections of stories about real-life criminals from the time period. They became a public obsession, especially among the middle class—much like today’s true crime dramas and podcasts. There were two reasons people liked them so much: They were about “real people” instead of the aristocracy (though sometimes they cited fictional characters like Robin Hood), and folks at the time were really paranoid about crime.
During the 1700s, there was heightened public anxiety around crime, and people wanted to understand the criminal mind better. Hence why they loved reading criminal biographies. But at the same time, they were not about forgiving and forgetting those who were committing these acts. According to historians, folks at the time viewed crimes as sins. They didn’t think the people committing the misdeeds were bad, necessarily, but they did see their actions as sins that had to be atoned for. That usually meant through capture and punishment. In addition, there was a belief that criminal biographies shouldn’t just entertain, but also impose morals, steering folks away from a life of crime. As a result, criminal biographies ended up sensationalizing a lot of stories, but usually did not give them fake happy endings, because they were also designed to steer folks away from what was seen as moral impropriety.
If you’ve seen films like Gold, Catch Me If You Can and any just about any Captain Blackbeard movie, it’s clear that Hollywood isn’t beyond changing biographies in order to tell a better story. That includes stories of real-life criminals. There are examples of Lovable Rogue stories being given happy endings that didn’t actually happen, usually years of decades after the events occurred.
A major example would be the Great Gold Robbery of 1855, one of the most famous train heists of the 19th century. A bunch of gold bars were locked in safes on a train bound from London to France. Upon arrival, it was discovered they had disappeared without a trace. The investigation lasted months, eventually leading to the arrest of three men including William Pierce. A century later, Michael Crichton turned this real event into a book and movie called The Great Train Robbery, with Sean Connery as William Pierce. Only in his version, William escaped using a key that a woman smuggled to him during a passionate kiss on the courthouse steps. That... didn’t happen to the actual guy.
So, why are stories like William Pierce’s fictionalized so they become the hero that got away? Why change actual history? Well, it’s because we’re more empathetic to criminals the more fictional they become. Whether it’s through the passage of time or romanticization of their acts—or having them be actual fictional characters, like Deadpool. It lets us see their actions as ideas instead of as part of their crimes. True, there are other factors involved. Criminal justice is complicated and has changed over the years. Plus, our own bias comes into play. But there is a reason why, earlier this year, a guy called himself a “lovable rogue” as his actual criminal defense. Smuggle some stuff off a train, you’re breaking the law. But do it with a smirk on your face and a Wookie by your side. Suddenly, you’re a hero.
Clarification: Earlier version of post cited MacNaghten as being from Scotland when his story comes from Ireland. This has been fixed.