Most people think of most criminals as what they are: bad people who break the law. For the most part, we don’t cheer on the common mugger or the cold-hearted killer, we don’t praise the embezzler or the fraudster, and we don’t look up to the drug runner or car thief. So why is it that certain types of crime and certain individual criminals tend not only to not be vilified, but are often even celebrated? Why do some crimes, like bank robbery or art theft, often have a romantic, exciting edge to them? After all, they’re still crimes, and crime is bad.
More often than not, the reason certain criminals become de facto pop culture celebrities is simply because people don’t have all the facts. When only a few facets of a criminal’s history are known, he or she may indeed come across as a dashing, sexy figure that we might not only respect but even envy. The more you know about a criminal, however, the more likely you are to realize how few lawbreakers actually deserve anything other than disdain and punishment.
If you think of any of the criminals on this list as dashing heroic types, just read on to learn that, in fact, they were pretty much just bad people.
15. Jay Z
Today the musician and producer known by his stage name, Jay Z, is generally considered to be a law-abiding citizen. However, in his younger years (and not quite so young years) he was little more than a violent criminal. Jay Z has admitted to selling drugs, to shooting his own brother (non-fatally), and to various other crimes and indiscretions. He likely also stabbed a man in a nightclub. Like many rappers, rock stars, and other artists, Jay Z’s celebrity largely rests on his background as a troubled, lawless, and violent man; it’s part of his aura and legend. But really it should denigrate, not elevate him: after all, he shot, stabbed, and sold drugs to people.
14. Jesse James
Today, many people see Jesse James as a dashing, daring figure who flouted laws and social mores but was an overall admirable character, known for giving the spoils from his many crimes to the poor and destitute. In fact, he was just a murderous robber. James got his start as a Confederate guerilla, battling Union troops during the Civil War when just a teenager, often killing men who were unarmed and actively trying to surrender. Which is not cool. Later, after the war, James and his gang robbed banks, trains, and stagecoaches. James was eventually shot dead by a member of his own gang who hoped to collect a reward out on the 34-year-old’s head.
13. Lucky Luciano
Considered by many to be the father (or should I say godfather) of the modern mafia, Lucky Luciano was one of the most famous criminals alive when he died in the mid-20th Century. He was street tough as a kid, a booze smuggler during the Prohibition years, a racketeer, and a negotiator who allegedly helped the United States military forge ties with Sicilian crime families during WWII. He cuts a dashing figure, in a lot of ways. But let’s not forget that we was also a pimp and a ruthless killer who ruined many lives and helped create a criminal network that is still extant today.
12. Pablo Escobar
If you watched the Netflix series Narcos, chances are that, at one time or another, you found yourself rooting for Pablo Escobar, the Colombian cocaine kingpin largely responsible for the influx of narcotics in the 1980s and one of the reasons for the so-called War on Drugs still being “waged” by American law enforcement personnel today. Escobar did some good things for his impoverished home community, yes, but mostly what he did was cause the deaths of dozens of people directly and thousands of people indirectly by playing a pivotal role in the increase in production and distribution of illegal drugs.
11. Richard McCoy, Jr.
On April 7th, 1972, Richard McCoy, Jr. highjacked a United Airlines flight and made off with $500,000 when he leaped from the plane wearing a parachute. He used a fake grenade and an unloaded pistol during the highjacking, which makes it clear he never intended to hurt anyone. After his arrest a few days later, he briefly went to prison, but broke out using a fake gun he crafted from dental paste. Seems like kind of a clever, cool criminal, right? Well, he also tried to kill federal officers who came after him following the breakout, dying in a gunfight. And also he left behind a wife and two kids.
10. Baby Face Nelson
Generally when you can see that a gangster’s lifespan was less than three decades, you can safely assume he or she was a pretty terrible person. Today the name Baby Face Nelson might not make you think of a ruthless, hardened killer and might instead call to mind a romanticized Prohibition Era rogue facing the authorities as he took what he pleased. But no, this guy was garbage. He robbed banks, robbed homes, killed perfect strangers over slight offenses (road rage, e.g.) and engaged in shootouts with the police. Fortunately he was killed before his 26th birthday, cutting short a “career” that surely would have left more grief in its wake.
9. Butch Cassidy
Maybe he was played by Paul Newman in a hit movie and maybe he was the head of the Wild Bunch, one of the most famous and romanticized group of Wild West Era bank robbers, but Robert Leroy Parker, AKA Butch Cassidy, should be remembered as a robber and killer and that’s about it. His string of crimes led him across the American west in the late 1800s and likely as far south as Tierra del Fuego right at the southern tip of South America. Cassidy made his way north as far as Bolivia, where he was shot to death in 1908.
8. John Dillinger
John Dillinger was a celebrity even in his own day, seen as something of a folk hero fighting back against the oppressive forces of Depression Era America. Of course all he and his gang were really doing was robbing banks and killing people. Dillinger and his cadre were responsible for at least ten deaths, seven serious injuries, and for tens of thousands of dollars stolen. The moral of the story here is that, more often than not, good people don’t end up shot to death during a gunfight with FBI agents. That’s how he died, at the ripe old age of 31.
7. Jack the Ripper
Alright, perhaps no one celebrates Jack the Ripper, exactly, but this unknown 19th century serial killer today enjoys something of a macabre celebrity status nonetheless. He is more a source of interest and scintillation than revulsion, at any rate. But really, he should pretty much disgust us, whoever he was. “Mr. Ripper” murdered at least five London prostitutes in the year 1888. His target of choice shows an inhuman cruelty, as clearly this killer was going after people the least likely to be protected by the criminal justice system and the least likely to be missed by society. In other words, he just really wanted to kill people.
6. Robert Downey Jr.
Downey Jr. is a fine actor and seems to be, these days, a decent human being. But were he not an actor, and one who plays the major role of Tony Stark/Iron Man in a number of blockbusters, he would just be some guy with a bunch of drug arrests. Like…a bunch. The actor was arrested for possession of everything from pot to coke to heroin to weapons, giving him a wrap sheet that would plague most people’s lives forever, preventing them from getting menial jobs, much less from becoming fabulously rich and famous. We have a much shorter memory for celebrities than we do for run-of-the-mill repeat offenders.
5. Whitey Bulger
Now the subject of several books and movies and known all around the world, James “Whitey” Bulger was already well-known and largely beloved in his native home of South Boston. Bulger grew up and grew into a criminal there in the 1930s and 40s. His first arrest came in his early teens, and by the time he was in his mid-20s, Bulger was in federal prison. He would return to Boston after getting out of prison in 1965, where his criminal activity intensified. Bulger is thought to have killed multiple people, but surprisingly he didn’t perpetrate a homicide until he was already in his 40s, which is unusual for most murderous criminals.
4. Charles Manson
Most people who even still remember Charles Manson know him for who he is: a psychopathic piece of garbage not worth the air he breathes. But some people still consider this twisted cult leader a romantic, compelling figure worthy of interest and even devotion. To be fair, Manson had a wretched childhood spent bouncing between homes and correctional facilities. Also to be fair, so have other people who have not grown up to be terrible people who pointlessly incited a bunch of brainwashed idiots to murder innocent people. But that’s what Manson did. Now well into his 80s and still in jail, he’ll soon enough be dead and gone.
3. Billy the Kid
Billy the Kid, AKA Henry McCarty and also known as William H. Bonney lived to be all of 21 years old. That’s an age at which few people have developed any real sense of maturity or restraint, and indeed it is the tender age at which the Kid died, which helps to explain the allure of this celebrated outlaw. Maybe he would have grown up into a decent man; we’ll never know. What we do know is that this “kid” killed several people, and some of them in cold blood. He also took part in multiple armed robberies, which is also not cool, kids.
2. Robin Hood
OK, so the Sheriff of Nottingham was definitely a jerk, that much I’ll grant you. Robin Hood and his Merry Men were probably justified in fighting back against this corrupt authoritarian who abused the power invested in him for his own gain. But not every rich person in the Dark Age/early Medieval England was a bad person, surely; so most of the time when Robin Hood, Little John, and the rest of the gang were stealing from the rich and giving to the poor, they were just robbing people, really. And timeless ballads, Disney movies, Kevin Costner’s no-accent performance, and all the rest of it notwithstanding, robbing people is not cool, Robin Hood.
1. Bonnie and Clyde
We think of Bonnie Parker and Clyde Barrow as this amazing, romantic couple who told the whole world to kiss of, living and loving the way they chose. Really, though, they were a couple of terrible people who both died violently while still in their early 20s and who left behind nothing but a string of corpses and money stolen from innocent people. The couple were celebrities in their own (brief) time, known to mug for the camera and seen all over newspapers of the early 1930s. Far from the sexy, carefree life they seemed to be living, they spent most of their two year crime spree in hiding before being gunned down on May 23rd, 1934.
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