Famous Fuckboys Throughout History


Fuckboys. We love to hate them and hate to love them. They’re a unique species of asshole that blends charm, wit, apathy, and risk together in an irresistible package that should come with a larger warning label than a pack of cigarettes. When the term arises in conversation, there’s usually one particular guy who automatically springs to your mind. And in all honesty, even if the guy who you’re likely currently picturing did happen to come with a giant neon sign around his neck, you’d probably choose to ignore it.

While it might seem like fuckboys are a relatively new category of male, upon closer examination it becomes blatantly obvious that they’ve been around for decades. Look at David Wooderson (Matthew McConaughey in Dazed and Confused), John Bender (Judd Nelson in the The Breakfast Club), and Mr. Big in Sex and the City. All three exhibit traits of a stereotypical fuckboy: emotional indifference, unflappable cockiness, high consumption of drugs or alcohol, and a tough exterior. Fictional characters are not the only notable fuckboys throughout history, by any means. Here are four famous fuckboys who prove that a rose by any other name would smell as sweet.

F. Scott Fitzgerald

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Although Fitzgerald only lived to be 44, he certainly gave the hard-partying lifestyle the old college try for the duration of his time on earth. Fitzgerald is famous first for his notable literary accomplishments, he penned The Great Gatsby and The Beautiful and Damned, among others. But second for his fuckboy reputation. Fitzgerald lived amidst the roaring twenties and viewed the world as his oyster. A hedonist if ever there was one, he spent night after night getting wildly intoxicated while partying into the wee hours of the morning with other Jazz Age dramatics. Shockingly, this carefree lifestyle began to wreak havoc on his marriage to Zelda Fitzgerald. Zelda spent much of the later half of her life in insane asylums, probably because Fitzgerald, being the fuckboy that he was, was driving her to madness. In the last few years of his life, Fitzgerald took up with a gossip columnist who was with him the evening before his death. Unsurprisingly, life and relationships cannot be sustained by liquor and parties alone, although try telling that to the hardest partying fuckboys on your campus.

Frank Sinatra

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Ol’ Blue Eyes. Mr. Steal Yo Girl. Actually, that last one might be Trey Songz. Regardless, Sinatra was one of the OG fuckboys of the twentieth century. Sinatra was well known for his philandering and constant extramarital affairs. Over the years, he was linked with numerous women, from Ava Gardner to Lauren Bacall. All total dimes, all totally wrapped around his finger. Typically envisioned with a drink in one hand and a cigarette in the other, he split his time banging beauties and partying with his pals until the sun rose. Sounds like a modern day fuckboy, right? While on the surface Sinatra may have seemed like he had it all, partying until dawn without a care in the world, he also seriously missed Ava Gardner after their breakup. Late at night, he would allegedly shoot photographs of her with a pellet gun. So, like, I guess that’s what fuckboys did before the invention of the iPhone. If you can’t hit your ex with twenty texts after a long night of getting smashed, the next best thing is obviously to hit her picture with twenty pellets.

John F. Kennedy

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Arguably the most notorious flirt to have ever occupied the Oval Office, JFK gave fuckboys with political aspirations (*cough* Bill Clinton *cough*) everywhere hope that they could still pull major bitches while in office. Kennedy was a fuckboy who had his shit together, further proving that they can come in all shapes and sizes. Along with a plethora of rumors linking JFK to Marilyn Monroe, he also spent many an afternoon swimming in the White House pool with girl after girl, enjoying daiquiri after daiquiri. One of his most well-known flings began when Kennedy unceremoniously took a teenage Mimi Alford’s virginity after one of these typical sunny swims. The affair continued for over a year, hitting a major bump when Kennedy asked Alford to give head to his brother, Ted while he watched. Sort of like when a twenty-first century fuckboy asks you for a threesome, except completely different!

Mick Jagger

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If you’re the lead singer of one of the most popular rock bands in American history, how could you not be a fuckboy? Even Britney Spears (all hail) drew inspiration from the Rolling Stones, covering “(I Can’t Get No) Satisfaction” in 2000. The song is about commercialism and lust, with the last few lines even referencing a girl getting her period, thus not allowing Jagger to get any. If you had a penny for every time a fuckboy complained about not getting laid because a girl was on her period, you’d probably have the same amount of pennies as women that Jagger slept with (a LOT). Although Jagger had multiple serious girlfriends over the years, he was never dissuaded from his hard partying lifestyle. The suicide of his most recent girlfriend, L’Wren Scott, took a serious toll on Jagger, proving that it might be possible for fuckboys to have feelings after all.

It is becoming more and more blatantly obvious that the fuckboy phase has no clear expiration or end in sight, and the dude that you were hoping would grow up postgrad may never actually change his heavy drinking, smoking, nefarious ways. Stay woke, ladies. And maybe stay away from the 30-year-old still rocking Chubbies.

Images via here, here, here, and here.

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A native Seattleite and self-proclaimed Snapchat queen, she's been a coffee addict since she found out what a coffee bean was. Believer in and promoter of the #freeguac and #freegucci movements. She is obsessed with all things Harry Potter and has been known to stop people at parties to tell them how to remove the wine from their clothes. In her spare time, she enjoys baking, writing for TSM, and pretending like she has her act together. Hit her up @

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