#4. John F Kennedy
Nowadays, John F. Kennedy is remembered mostly for getting shot in the head which, while admittedly badass, barely makes the top ten of badass things he's ever done. Plagued with a bad back his entire life, Kennedy was disqualified from service in the army. Instead of using this as an excuse to pursue the decidedly more sane strategy of staying the fuck away from explody things, Kennedy had his dad pull a few strings so he could sneak his way into the navy, where he eventually became a lieutenant. Just to get some perspective, Bill Clinton dodged the draft, Grover Cleveland paid someone else to go in his place when he was drafted, but Kennedy beat the system by forcing his way into the navy. Once there he handled himself like a gravel eating shit-miner, instead of the rich Boston pretty boy he actually was.
Today, he's got his own damned aircraft carrier named after him.
The USS John F Kennedy can launch 80 planes and can single-handedly win a war with most countries on Earth
Upon leaving the Navy, he took up boning on a near full-time basis. Sure, he dabbled in being a Senator and a President or whatever, but his full-time job was Pimping. In fact, if boning-your-girlfriend-right-in-front-of-you was a business, you can bet your cuckolded ass that Kennedy would have been its District Manager.
While almost no two sources are in agreement as to just how much tail Kennedy snagged, historian John Richard Stephens says that "Kennedy confided with friends that he could only be satisfied with three women a day." It's amazing that, with all this boning, Kennedy didn't lose focus and make any colossal screw-ups while in office, and-...What? Bay of what? Moving on.
JFK's sexual conquests allegedly include Marilyn Monroe, Audrey Hepburn, Jayne Mansfield, Angie Dickenson, Brazilian actress Florinda Bolkan, famous burlesque stripper, and rap name pioneer Blaze Starr. There are even rumors that he also had sex with his insanely hot wife once in a while too.
Greatest Display of Badassedry:
In August of 1943, while serving as skipper of the PT-109, Kennedy's boat was ripped in two by the Japanese destroyer Amagiri. Kennedy and his crew were tossed into the water and surrounded by flames. Kennedy, despite a chronic back injury and an even more chronic boning-induced-exhaustion, managed to swim four hours to safety while towing an injured crewman by the life jacket strap with his teeth. His fucking teeth!
Most Badass Quote:
"Jack could be shameless in his sexuality, simply pull girls' dresses up and so forth. He would corner them at White House dinner parties and ask them to step into the next room away from the noise, where they could hold a 'serious discussion.'"
That quote comes from Kennedy's closest friend, Lem Billings. For proof that you will never be as badass and pimpsational as Kennedy, go ahead and try that "Hey baby, let's go have a serious discussion" line on any girl and then come back and tell us how much sex you didn't have.