Top 10 Shady Asshole Bros Throughout History

Woody Allen, Kobe Bryant, the Biebs, any bro who's ever competed on The Bachelorette, and so on – famous dudes constantly find new ways to sketch us the fuck out. However, don’t forget that bros have been doing shady shit since before the Internet was around to immediately let us know they did shady shit. Let’s take a moment to recall philandering, scandals, and other shadiness throughout history, because it's almost Valentine's Day and the Internet should never forget.

King Henry VIII

This bro founded an entirely new church just so he could get a divorce and marry a new betch who #8 wasn’t having sex with him, beheaded her when his baby batter didn’t produce a boy, and went through four more wives before dying of obesity. Something to think about next time a pro doesn’t text back.

Benito Mussolini

^ Sex machine

The Italian dictator had women brought to him every day, participated in massive orgies, and called the idea of monogamy “inconceivable,” serving as an inspiration to his Italian-American brethren of MTV demi-fame.

Benjamin Franklin

He gave us a lot of good things, like the lightbulb and something to call our $100 bills, but dabbled on the shady side. For example, in a letter from 1745, he advised a fellow revolutionary bro to hook up with old haggard women instead of young ones, because 1) all the shit looks the same if you cover the head with a basket and 2) they are “so grateful.” There’s also the whole syphilis rumor…

John F. Kennedy

JFK claimed that he got headaches if he didn’t have sex every day, so instead of popping whatever Mad Men had in lieu of Xanax, he ostensibly slept with every vag around.


Bill Clinton

And then they fucked.

Bill aka Slick Willy is the only president who can claim to have spent a year fighting over the definition of sex with Congress and almost getting fired for it. Two words: Hillary Clinton. Can you blame him?

Anthony Weiner

Pro tip – if you’re going to be a public official who insists on sending dick pics over highly traceable and easily stored forms of communication, you might want to change your last name to something less phallic. Fucking duh.

Frank Sinatra

I can't believe my grandparents used to stalk celebrity mugshots too.

Pulled plenty of John Mayers before John Mayer existed. Sinatra’s main technique was to tell women he wanted to marry them before executing the D.E.N.N.I.S. system. Fun fact: in 1938, he was arrested for seduction and adultery of a female of ‘good repute’ (old speak for nicegirl).

Hugh Grant

Never mind the fact that he was arrested for getting a beej in his car from a prostitute while still married to Elizabeth Fucking Hurley (see above). Hugh Grant apparently thinks that he’s the prime minister in real life, not just in Love Actually, and is trying to unite the world by spawning a love child with a woman from each country (completed: China, Sweden).

Jerry Springer

Back in the 70’s, Jerry Springer was busted for patronizing a “massage” parlor in Kentucky. Strangely, the scandal ended up boosting his political career before he started his talk show; now, he’s the highest paid television show host in the world. Suck it, Seacrest?

Tiger Woods

With a new sex scandal coming to light like, every week, you may have forgotten 2009’s golf club whack heard around the world. Tiger didn’t realize that obvs it’s an unwise idea to piss off a BSCB, and his two five many-timing ways led to car crashes, millions of dollars in lost endorsements, one of the largest divorce settlements of all time, and a tangentially related admission of drug abuse.


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