If history wasn’t your favourite topic in school, perhaps your teacher wasn’t finding ways to make it relevant to what you really care about. History is so much more fun when you add sex. We’ve rounded up five of the most famous men in history, the guys who shaped the future of the world and who just happen to have some of the most famous penises in history.

1. Grigori Rasputin (aka The Mad Russian)

Grigori Rasputin was a Russian mystic, political advisor and all around strange man. The Russian Tsar Nicholas II and his wife, Tsaritsa Alexandra, believed him to be a prophet, a faith healer and a confidant. When he wasn’t advising Russian royalty, Rasputin was out on the town, getting drunk, having sex and causing plenty of trouble. Stories about his sexual powers spread throughout the area and continue to be discussed today. According to one account, a woman who had sex with the Mad Russian had an orgasm so intense she fainted. After Rasputin was murdered in 1916, his penis was severed from his body and was kept by a variety of owners throughout the years. Today, Rasputin’s penis has a place of honour in the Russian Museum of Erotica where it has become one of the museums biggest attractions.

2. Juan Baptista dos Santos

Born in 1843 with three legs, Juan Baptista dos Santos was pretty much destined to have a career as an exhibitionist. Santos didn’t go the typical Circus Side Show route, however. He limited his exhibitionism to the medical community which was interested in another physical anomaly – his extra penis. Santos is one of the few well documented cases of diphallia, the condition where a man is born with two penises. The photographer C.D. Fredericks worked with Santos to capture the only known photographs of his condition and claimed that each penis functioned normally so Santos could have sex to completion with one penis and then carry on with the other.

3. David

The statue of the Biblical King David by Michelangelo is perhaps one of the most iconic and easily recognizable works of art throughout human history. The statue was created in the early 1500s and has survived wars, earthquakes and even the Victorian zeal of removing any signs of sexuality from art, literature and society. David managed to survive this Victorian zeal for propriety thanks to a detachable fig leaf which was created in order to appease Queen Victoria. The statue of David has sparked a number of protests throughout the years but remains one of the most popular works of art in the world. Reprinted and broadcast countless times in book, magazines, television and movies, David’s penis has been seen by more people than any other.

4. Napoleon

Napoleon just can’t catch a break. Not only did he suffer from the most iconic case of Small Man Syndrome, his penis has become a historical artefact that was recently closely examined for a British television series and found to measure it at a not very impressive inch and a half. For some, this puts some credence to the concept of there truly being a “Small Man’s Syndrome”. Napoleon’s penis has circulated through a number of collectors over the years and is now in a private collection of a Urologist in New Jersey.

5. John Holmes

Most people know exactly who John Holmes is and why he’s famous. Measuring up at 13 and a half inches (according to his long-time friend and colleague Bill Amerson) Holmes took the adult film world by storm when his career took off in the early 1970s. He eventually became well known for his recurring character Johnny Wadd, and his career and lifestyle would later form the inspiration for the role of Dirk Diggler in the 1997 hit ‘Boogie Nights’. While his record breaking penis brought him fame and fortune – albeit temporary fame and fortune – his continuing legacy is what earns him a place on this list. Holmes’ member and the public’s fascination for it, was one of the leading contributors to mainstream acceptance of pornography as well as ushering in a more open minded approach to sex in general.