For centuries, society has cheered for men who racked up the greatest number of “conquests”—conquests of women, that is. Apparently sleeping with thousands of women is a badge of accomplishment in some circles. And even several popes have bragged about their sexually activity. But the biggest playboys in history were also pretty terrible human beings.
The men on this list were all huge scumbags who treated women like garbage. When Fidel Castro wasn't palling around with Che Guevara, he was scouring the beaches of Havana for his next “meal.” Pablo Picasso drove two of his lovers to suicide, while Henry VIII beheaded two of his. But at least one of the men repented on his deathbed, warning others not to idolize his sexual exploits.
From Hugh Hefner’s scheduled group sex nights to Lord Byron’s pubic hair collection, these lotharios were not the greatest male lovers in history—they were historical womanizers who should be exposed for their exploits. And now it’s your turn to weigh in on the sleaziest playboys in history.
Today, Genghis Khan has 17 million direct male descendants—which placed him on one list for having one of the greatest sex lives in history. But it’s not very impressive once you consider how Genghis Khan made himself the genetic ancestor of 8% of Central Asia’s population. Genghis Khan was a ruthless conqueror who slaughtered his enemies and raped countless women. He reportedly even claimed that
“...the greatest joy for a man is to defeat his enemies, to drive them before him, to take from them all they possess, to see those they love in tears, to ride their horses, and to hold their wives and daughters in his arms.”
Gross. Rapists are automatically scumbags.
Birthplace: Delüün Boldog
Fidel Castro might not be the first name that comes to mind when you hear “suave playboy”—but the Cuban dictator supposedly slept with 35,000 women in his lifetime. For Castro, it was all about racking up the numbers, not about the women themselves. Castro sent out his guards to recruit beautiful women on the beaches of Havana to keep up with his appetite, as if he were ordering take-out. And he paired sex partners with his meals, aiming for a different “lunch” and “dinner” partner every day. As if that weren't gross enough, Castro also admitted to sleeping with girls as young as 15, which is a crime in Cuba (and pretty much everywhere else).
Birthplace: Birán, Cuba
Profession: Politician, Lawyer
Ian Fleming is famous for creating James Bond, but his real-life exploits are almost as crazy as his fictional hero’s. And just like James Bond, Fleming spent a lot of his time seducing beautiful women. One female friend said of Fleming, “No one I have ever known had sex so much on the brain as Ian.” But for Fleming, it was apparently all about the conquest—he told a friend that women were like pets or dogs. To him, they were not real human beings like men. In addition to his misogyny, Fleming was kicked out of a military academy in Britain because he had gonorrhea.
Age: Died at 56 (1908-1964)
Birthplace: London, England
Profession: Journalist, Novelist, Author, Writer
Casanova’s name made it into the dictionary as a synonym for playboy, but he shouldn't be anyone's hero. The real Giacomo Casanova was born in 1725, and he nearly became a priest before he was expelled for sleeping with another student. After leaving the seminary, Casanova devoted himself to seducing women. "Cultivating whatever gave pleasure to my senses was always the chief business of my life," Casanova wrote in his autobiography. But it wasn’t all fun and games. Casanova also admitted to forcing a peasant girl to have sex with him and beating a prostitute when she refused him—plus, he most likely spread gonorrhea and syphilis to his many partners.
Age: Died at 73 (1725-1798)
Birthplace: Venice, Scorzè, Italy
Profession: Librarian, Author, Writer