The World's 15 Sexiest Criminals

One of the stranger trends going around the internet these days is swooning over attractive criminals. No, society’s moral fabric hasn’t fallen apart; we just tend to operate on a far shallower level

One of the stranger trends going around the internet these days is swooning over attractive criminals. No, society’s moral fabric hasn’t fallen apart; we just tend to operate on a far shallower level on the taboo-lite interweb  — leagues shallower, where risk, danger and chiseled jaws draw endlessly more attention than just being a stand-up guy or gal like everyone else. Of course in real life, criminality doesn't exactly invite a positive reaction - but the hot criminal is an intriguing juxtaposition that we can't help but theoretically enjoy.

Ironically, thinking about sexy criminals made us realize even the web has limits to its debauchery. We set about this list being, of course, a little tongue-in-cheek — applying that superficial hotness standard to people who, under far more significant standards, would usually be considered totally not. But it turns out sometimes that play just can’t be made. Ted Bundy for example — serial killer and dead body desecrator — happened to be a dashing dude. But those charms directly led to serial killing and facilitated his necrophilia, and no amount of tongue in your cheek could possibly say “that dude was sexy”.

So if you find this list upsetting, just remember it could be lot worse. We've limited it to 15 criminals who, despite their bad behaviour, make some tiny modicum of our shameless monkey brains still say I’d hit that. 

15 Jesse James

Jesse James robbed prodigious trains and banks and murdered anyone who stood in his way. All that aside: that’s a good jaw. Since he steered down the path of 19th century thug life, he mostly ran from bootstrapped sheriffs; had he not, he’d still invite chase from the ladies. The man was born to be on the run, and that handsome mug of his (which Robert Ford eventually ruined, the coward) no doubt explains part of why today’s fetishism of criminals even exists.

14 Bonnie and Clyde

Both charmers in their own rights: Bonnie often posing with her cigarette, revolver and high heels, Clyde with his suit, slicked hair and shotgun. Together, under a spell of youth, love and larceny they invented criminal romance. But it’s not so much their looks as the way the couple embodied that  “you and me against the world” attitude so literally. Robbing banks, sticking up gas stations, and ostensibly canoodling each other every night—ultimately dying young, but together in love.

13 Harry Pierpont


A textbook hunk: over six feet tall, blue eyes, soft-spoken, smart and loyal to his bros. His bros might’ve been Prohibition gangsters, and he may have exploited his dashing qualities to coordinate brazen bank robberies in the 20s and 30s, but still Harry Pierpont wasn’t like all the other guys. Shy and uncomfortable in the spotlight, how did such a sensitive (alternatively: cold and calculated) hottie lead such a high-profile life of crime? Why, by letting his friend and fellow smokeshow take all the credit…

12 John Dillinger


Pierpont was the brains behind depression-era gangsterism, but Dillinger’s Hollywood looks and daring attitude made him the face and personality. With Pierpont and the gang he robbed two dozen banks and four police stations, leading a freewheeling lifestyle hiding out in brothels, escaping from jail twice and captivating the public consciousness as public enemy number one. But his worst crime of all was the countless hearts he stole along the way. Alright no, seriously, his worst crime was killing a police officer.

11 Pretty Boy Floyd


He hated his cute nickname, but luckily he had a badass one as well: “The Robin Hood of the Cookson Hills.” Despite being a prodigious bootlegger and bank robber like his contemporaries, the public adored Charles Arthur “Pretty Boy” Floyd. That’s because Floyd did two things right: maintained boyish good looks, and destroyed tons of mortgage documents during his bank robberies which happened to free countless people from debt.

10 Bugsy Siegel


We like to believe he would’ve made a dashing game show host. Instead, Bugsy Siegel joined the cause of establishing the Las Vegas Strip and a nation-wide syndicate of contract killers for the American Mafia. His specialities included racketeering, bootlegging, drug trafficking and murder. But don’t trust anyone who says those eyes don't make them melt, just a little.

9 Evelyn “Billie” Frechette


Billie Frechette was guilty of one thing: being John Dillinger’s cute girlfriend. She spent two years in a Michigan prison for letting her bad boy hide out in her apartment, and just months after her arrest, police shot him down anyway. Poor girl. In the end she lived a quiet life in the Metis Reservation where she was born, leaving the cute to thoroughly outweigh the criminal in this story. Did we mention she was also a singer?

8 Amy Fisher

Once upon a time in the early 90s, Amy Fisher shot her lover’s wife in the head on her front porch. The victim survived, but suffered permanent physical and mental damage, and Fisher received a 15 year prison sentence for attempted murder. Dubbed the 'Long Island Lolita', she was 17 years old at the time. Fast forward to her early release in 1999, and she embarked on a career as a journalist in Long Island. At what point did Amy Fisher get photographed so scantily clad? When she became an adult entertainment star years later.

7 Matteo Messina Denaro


Italian magazine L’Espresso featured the above face on their April 2001 cover headlined: “Here is the new boss of the mafia”. Matteo Messina Denaro became notorious overnight. Denaro, who some call by the comic book villain nickname Diabolik, is considered one of Cosa Nostra’s new leaders and one of the ten most wanted criminals in the world. What few photographs of him exist are shrouded in super cool mystery — a cold cement expression underneath a set of aviators, and great hair. Legend has it he’s a ruthless womanizing playboy addicted to luxuries and explosive violence. He’s been running since 1993.

6 The Cellphone Bandit


Candice Rose Martinez made headlines in 2005 as a super hot 19-year-old who robbed four banks in Northern Virginia while talking on her cellphone. Along with her boyfriend/getaway driver/cellular dispatch, she stole a total of $48,620 before her arrest and 12 year prison sentence. A real shame, since she could've made a killing selling skin cream.

5 The Sexy Robber


That’s actually what the cops called her. In this video capture from 2011, some sexy woman peruses a jewelry store. A few seconds later, she sexily pointed her revolver at the jewellery store owner and demanded loot. She fled (sexily) in high heels and remains at large. LAPD describe the suspect as armed, dangerous and incredibly sexy.

4 Foxy Knoxy

Meredith Kercher’s murder became so shrouded in mystery and speculation that the only thing people know with certainty is that her accused killer is bizarrely enchanting. With a combination of good looks and enigmatic behaviour, Amanda Knox took the law and the media on a roller coaster of conjecture, doubt and suspicion as to whether she took part in her roommate’s killing in 2007. Conflicting alibis, false accusations and shaky forensic evidence: Last January, Italian courts sentenced Foxy Knoxy, the femme fatale, to 28 years in prison, but Amanda Knox — maintaining innocence — remains free in the US pending appeal.

3 Casey Anthony


On one hand she isn’t exactly a convicted criminal. On the other, if she was it would confirm some pretty egregious stuff that would obliterate every scrap of sexiness you could find. Does Casey Anthony deserve to be on this list? If you ask the internet, several “hot Casey Anthony” picture compilations answer loud and clear. Her youth and looks no doubt contributed to the attention Anthony's trial received, and today, as long as doubt still exists that this woman was involved in her two-year-old daughter’s death (she was found not guilty) people will entertain the thought that she is, in Howard Stern’s words, a “stone-cold hottie”.

2 Jeremy Meeks


Here is the angelic face that damned the internet to sexy criminal addiction. Jeremy Meeks was one of five Californian men arrested in a gang sweep last June and the only one who might probably be the better for it. Despite 11 felony counts related to firearms, street gang activity, and violating probation, Meeks’ mugshot landed him world wide web fame and — God save us — a modelling contract if and when he gets out of prison. To think we could one day see “one of the most violent criminals of the Stockton area” (he once beat a teenager, almost to death) posing for Armani.

1 Stéphanie Beaudoin

And alas, the latest chapter in this debauched development: Last Thursday, the above Quebec beauty's picture went viral as the “hottest alleged thief on the planet”, after her arrest on 108 separate charges including breaking and entering, thievery, and criminal firearm possession. Stéphanie Beaudoin, 21, returns to court this November, and the world will no doubt be watching her chest.

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The World's 15 Sexiest Criminals