Scammers and swindlers are nothing new: as long as humanity has existed, there has always been a certain group of people who enjoy telling tall tales and tricking others out of their possessions. However, these five individuals below truly stood out among the others, be it due to their sheer dedication or the sheer insanity behind their lies. Be it for money power, or just for the fun of it, here are five of history’s most iconic and infamous imposters in all of history.

1. Cassie Chadwick

Cassie Chadwick, born Elizabeth Bigley, was a 19th century con artist who first started off with some minor forgery in her native Canada, before setting her sights on the United States. There, she pretended to be a clairvoyant in many cities all over the country. One of boldest antics was when she befriended a lawyer named James Dillon, an acquaintance of the wealthy Andrew Carnegie. Claiming to meet Carnegie for important business, Chadwick had Dillon drop her off at Carnegie’s house where she instead spoke with the head housekeeper under the guise of checking the references of a maid she wanted to hire.

2. Fred Demara

Fred Demara, or “The Great Imposter,” as he’s so affectionately known, was a man who changed his identities and profession like hats, many he was hardly qualified for. His resume is quite a large one: he was a Trappist monk, dean of philosophy, prison warden, law student, civil engineer and even a naval surgeon who performed legit surgery. Demara had many people totally fooled over the course of his life—they only found out about his schemes after he sold his story to Life magazine. It certainly helped that he had a very high IQ and photographic memory which aided in his charades.

3. John Deydras

Sometime in the early 14th century, a man named John Deydras walked right into the Beaumont Palace in Oxford claiming that he was in fact the real Edward II. Deydras further expounded his story, saying that his fearful nanny switched him with a random boy after a sow bit off his ear while he was playing with it. Rather than being offended king Edward II was rather amused and kept him as a court jester. However, his wife wanted Deydras gone, and imprisoned him until he confessed that the whole thing was a ruse planned by his possessed cat. Both were later assassinated.

4. Lord Gordon-Gordon

Lord Gordon-Gordon was a smooth-talking 19th century British man who swindled many people after successfully impersonating a Scottish landowner. His victims were all wealthy businessmen who he convinced into loaning him tens of thousands including the railroad magnate, Jay Gould. Gordon-Gordon scammed Gould out of half a million dollars which he was only supposed to hold on to. When the jig was up, Gordon-Gordon immediately fled to Canada for safety, but instead took his life upon learning that he was set to be extradited to the US.

5. George Psalmanazar 

George Psalmanazar impressed the 18th century London residents with tales of his so-called native homeland, Formosa now known as Taiwan. He further convinced them of his stories by eating unusual foods and performing strange rituals, making his lies seem more believable. At one point during his travels, Psalmanazar stumbled upon a Scottish chaplain named Alexander Innes who “converted” him to Christianity and then brought him over to London. Along with his other insane and exaggerated lies, Formosa remained highly popular among the public for only a few years until they got tired of him.