41 — Leonidas I


a.k.a: Leonidas The Brave

Occupation: King

Born: circa 540 BCE

Died: 480 BCE

Brief Description:
Leonidas was the third son of Anaxandridas II of Sparta. His mother was his father’s niece and had been unable to bear children for so long that the King had to take a second wife. His second wife bore the king’s eldest son, Cleomenes. Shortly after however, his first wife gave birth to Dorieus and later to Leonidas.
Because Leonidas was not heir to the throne, he was not exempt from attending the agoge, which made him one of the few kings to have undergone the training.

(Sparta was an unusual city-state in that it had two kings simultaneously, coming from two separate lines, the Agiads and the Eurypontids. The agoge was the rigorous education and training regimen mandated for all male Spartan citizens, except for the firstborn son in the two ruling houses. Even though exempt however, they were allowed to take part if they so wished, which endowed them with increased prestige when they ascended the throne.)

After Anaxandridas’ death, Cleomenes ascended the throne but the spartans considered him insane and put him in prison where he committed suicide.
Leonidas then married Cleomenes’ daughter, Gorgo, and succeeded to the Agiad throne. (Dorieus had already died by then.)

In 481 BCE, he was chosen to lead the combined Greek forces to resist the Persian invasion and in August 480 BCE, he went out to meet Xerxes’ army at Thermopylae with a small force of 300 men. (Supposedly, the oracle at Delphi had predicted that Sparta would either fall to the Persians or mourn the death of a king.) Other Greek city-states joined Leonidas to form an army of 14,000. In contrast, Xerxes’ army consisted of over two million men according to Herodotus (but he’s known for exaggerating so take this with a pinch of salt).

Xerxes waited four days to attack, hoping the Greeks would disperse and eventually attacked on the fifth day. Leonidas and his men repulsed the Persians’ frontal attacks for two consecutive days and even killed two of Xerxes’ brothers. On the seventh day however, a Malian Greek traitor led a Persian general by a mountain track to the rear of the Greeks. At that point Leonidas sent away all Greek troops and remained in the pass with his 300 Spartans and a few hundred Helots and Thespians who refused to abandon him.

Now by this time the spears of the greater number of them were broken, so it chanced, in this combat, and they were slaying the Persians with their swords; and in this fighting fell Leonidas, having proved himself a very good man, and others also of the Spartans with him, men of note, of whose names I was informed as of men who had proved themselves worthy, and indeed I was told also the names of all the three hundred. – Herodotus

Why he’s on the list:
Of my favorite 50, Leonidas is perhaps the character that needs the least explanation as to why he’s on my list.
It should be pretty obvious and straightforward, but just in case you’re blind…
Leonidas embodies all the virtues of a charismatic leader (courage, respect, honor, loyalty, integrity, selflessness, etc.) even when challenged by insurmountable odds.
He and his men, through their valor and sacrifice, have set an inspirational example for all of Greece.
According to Plutarch, when someone told him: “Leonidas! How are you going with so few to risk with so many?”, he said: “If you think that I am going to fight by numbers, then the whole of Greece would be insufficient, for she is only a small part of the numbers of the Persians, but if I am going to fight by valor, then even this number is enough.”

And of course, as is usually the case, characters I like need to have that extra confidence/arrogance. =)
According to Plutarch (again), “When someone said to him: ‘Except for being king you are not at all superior to us’, Leonidas son of Anaxandridas and brother of Cleomenes replied: ‘But were I not better than you, I should not be king.'”

42 — Hernan Cortes de Monroy y Pizarro

Hernan Cortes

a.k.a: The Marquis of the Valley of Oaxaca

Occupation: Conquistador

Born: 1485

Died: 1547

Brief Description:
Hernan Cortes was born in Medellin, Spain, to a family of lesser nobility. Around the age of fourteen, he went to study at the University of Salamanca for a couple of years and soon after, in 1504, left Spain to seek his fortune in the New World.

As Cortes reached Santo Domingo, the capital of Hispaniola, he registered as a citizen and settled in the town of Azua de Compostela where he served as a notary for several years.
In 1511, he joined Diego Velazquez in an expedition to conquer Cuba. Velazquez was so impressed by Cortes that he secured a high political position for him in the colony. As time went on however, the relationship between the two became tense and, in 1518, as Cortes was about to lead an expedition to Mexico, Velazquez changed his mind and revoked his charter. But Cortez ignored the order and set sail for Mexico anyway with 500 men, 11 ships and 13 horses.

Cortes became allies with some of the native peoples he encountered, but with others he used deadly force to conquer Mexico. He fought Tlaxacan and Cholula warriors and then set his sights on taking over the Aztec empire. As the Spaniards reached the Aztec capital, Tenochtitlan, they were received with open arms by Moctezuma II, the ruler of the Aztec empire, who thought Cortes to be the feathered serpent god, Quetzalcoatl, because he was of lighter skin, sitting on his horse and wearing metal armor. Nonetheless, Cortes took Moctezuma hostage and his soldiers raided the city. Led by Cuauhtemoc, Moctezuma’s nephew, the Aztecs rallied. Though reinforced, the Spaniards were besieged, then routed as they fled but they were soon back, and laid siege in turn. They finally took the city in 1521 and claimed it for Spain.

As a result of his victory, King Charles I of Spain (aka Charles V, Holy Roman Emperor) appointed him as governor, captain general and chief justice of the newly conquered territory, dubbed “New Spain of the Ocean Sea” but Cortes faced challenges to his authority and position. He traveled to Honduras in 1524 to stop a rebellion against him in the area. Back in Mexico, he found himself removed from power so he traveled to Spain to plead his case to the king but he was not reappointed to his governorship.

In 1540, Cortes retired to Spain and spent much of his later years seeking recognition for his achievements and support from the Spanish royal court.

Why he’s on the list:
I first heard about Cortes in my early adolescence. I didn’t know much about him at the time but the fact that he was a soldier, an explorer and an adventurer was enough to fuel my imagination.
As I grew a older, it was Cortes’ determined character and pioneer spirit that impressed me. He was willing to do anything to reach his goals. In one instance, he even scuttled his ships in order to eliminate any ideas of retreat among his men.
Today, as I am writing this, it’s his insatiable greed for gold, his desire to always have more, that fascinates me. It’s what capitalism is all about and I love it.

That being said, none of the points above would stand alone to put Hernando Cortes on this list. He’s on this list because he’s a character I liked for different reasons at different stages in my life. For me, he’s a reminder of how our vision of the world grows and evolves over time throughout our experiences, sometimes for the best, sometimes for the worst…

43 — Hippocrates of Kos


a.k.a: The Father of Medicine

Occupation: Physician

Born: circa 460 BCE

Died: circa 377 BCE

Brief Description:
Hippocrates, son of Heracleides and Praxithea, was born on the Aegean island of Kos towards the end of the fifth century BCE.
His family’s wealth permitted him to have a good educational beginning as a child after which, he attended a secondary school where he had a thorough athletic training.
He then went on to study medicine under his father in a form of apprenticeship by following him and another doctor, Herodicos, from patient to patient and observing their treatment.

Hippocrates became a famous ambassador for medicine but Greek politics and governance had opposed his theories and approaches. For this reason, the great physician had to spend two decades in prison. During that time, he wrote his very famous book of medicine ‘The Complicated Body’.

Hippocrates was not only a healer but also a teacher and founded a school of medicine in Kos.
He had many students of which, his own two sons, Thessalus and Draco, and his son-in-law, Polybus.

The ‘Corpus Hippocraticum’ is a collection of roughly seventy works and the oldest surviving complete medical books. Although the works have been written by people other than Hippocrates himself, probably his students and followers, it was attributed to him in antiquity as its teachings closely followed his principles.
The most notable treatise from the Corpus is the Hippocratic Oath. The oath is still in use today (albeit not in its original form) and serves as a foundation for derivative oaths taken today by medical graduates about to enter medical practice. In the oath, the physician pledges to prescribe only beneficial treatments, to refrain from causing harm or hurt, and to live an exemplary life.

Little is known of Hippocrates’ death other than a range of date possibilities but what lives on in modern medicine is his commitment to the treatment of disease.

Why he’s on the list:
For the content of the oath…

I swear by Apollo the physician and Asclepius, and Hygieia, and Panacea, and all the gods and goddesses, that, according to my ability and judgment, I will keep this Oath and this stipulation: To reckon him who taught me this Art equally dear to me as my parents, to share my substance with him, and relieve his necessities if required; to look upon his offspring in the same footing as my own brothers, and to teach them this art, if they shall wish to learn it, without fee or stipulation; and that by precept, lecture, and every other mode of instruction, I will impart a knowledge of the Art to my own sons, and those of my teachers, and to disciples bound by a stipulation and oath according to the law of medicine, but to none others.

I will follow that system of regimen which, according to my ability and judgment, I consider for the benefit of my patients, and abstain from whatever is deleterious and mischievous. I will give no deadly medicine to any one if asked, nor suggest any such counsel; and in like manner I will not give to a woman a pessary to produce abortion. With purity and with holiness I will pass my life and practice my Art.

I will not cut persons laboring under the stone, but will leave this to be done by men who are practitioners of this work.

Into whatever houses I enter, I will go into them for the benefit of the sick, and will abstain from every voluntary act of mischief and corruption; and, further, from the seduction of females or males, of freemen and slaves.

Whatever, in connection with my professional service, or not in connection with it, I see or hear, in the life of men, which ought not to be spoken of abroad, I will not divulge, as reckoning that all such should be kept secret.

While I continue to keep this Oath unviolated, may it be granted to me to enjoy life and the practice of the art, respected by all men, in all times. But should I trespass and violate this Oath, may the reverse be my lot.

44 — Jessica Stoyadinovich


a.k.a: Stoya

Occupation: Porn Star

Born: 1986

Died: Not Yet

Brief Description:
Stoya was born in North Carolina of a Serbian father and a Scottish mother. She was home-schooled and got her high-school diploma before the age of sixteen. Later, she moved to Delaware to attend college but dropped out. She then moved to Philadelphia where she started to pose for photo-shoots (with her clothes on). Gradually, she started posing nude then doing girl-on-girl scenes and eventually, everything else…

She is an exclusive contract performer for Digital Playground and is regarded as their first alt porn contract girl.
Her stage name “Stoya” was her nickname before appearing in adult films and is the shortened version of her family’s last name.
In 2009, Stoya won AVN’s Best New Starlet.

Why she’s on the list:
Technically, Stoya is not my favorite porn star: I don’t really have a favorite porn star but I do love porn stars in general. I also like the concept of porn and the idea of selling pleasures and fantasies.
I happen to love girls with huge plastic boobs, multiple piercings and full-back and sleeves tattoos. But Stoya lacks all these, so why her?
I don’t know. Maybe because she’s a porn star that just doesn’t fit the stereotype.

Physically, I like the fact that she’s relatively thin and tall with a strong contrast between her dark hair and light skin.
Intellectually, Stoya is smart, sharp and witty in a fun way. (At least that’s the public image she projects.)
She also likes to read. Seriously. Bonus points for being mentally twisted.
In general, it seems to me that Stoya is well-suited to be the placeholder and representative of porn stars on my list.

To recap: Porn stars are awesome and Stoya is awesomer so she gets a place on this awesomest list.

45 — Diogenes of Sinope

Diogenes of Sinope

a.k.a: Diogenes the Cynic

Occupation: Philosopher

Born: circa 412 BCE

Died: 323 BCE

Brief Description:
Diogenes is regarded as one of the founders of the cynic philosophy, which later inspired stoic doctrines. While the factual description of his life would sound boring, the anecdotes behind the man and his philosophy are awesome and give a deep insight into the character, so I shall focus on these…

Diogenes was born in Sinope (mordern-day Turkey). His father was a banker and it is likely he was helping him out. At some point, they became embroiled in a scandal involving the defacement of the currency and Diogenes got exiled from the city. Little else is known about his early life.
After his exile, Diogenes moved to Athens. There, he used his simple lifestyle and behavior to criticize the social values and institutions of what he saw as a corrupt society.
He made a virtue of poverty. He lived in a large ceramic jar and was known for carrying a lantern in the daylight, looking for an honest man.
Later in his life, he got captured by pirates and got sold to a Corinthian. Stories vary regarding what happened next but he most likely lived the rest of his life in Corinth, preaching his doctrines.


– When he was asked where he came from, he replied that he was a citizen of the world (cosmopolitan).

– When Plato gave Socrates’ definition of man as “featherless bipeds” and was much praised for the definition, Diogenes plucked a chicken and brought it into Plato’s Academy, saying, “Behold! I’ve brought you a man.” After this incident, “with broad flat nails” was added to Plato’s definition.

– When Alexander The Great met Diogenes. He was very thrilled to meet the famous philosopher and asked him if there was anything he could do for him. Diogenes, who was relaxing in the sunlight, replied: “Yes, stand out of my sunlight.” As everybody laughed, Alexander declared: “If I were not Alexander, then I should wish to be Diogenes.” To that, Diogenes replied: “If I were not Diogenes, I too should wish to be Diogenes.”

– When he once visited the magnificent house of a rich man, he spat in the rich man’s face then said: “I didn’t dare to spit anywhere else.”

– When he was going to be sold as a slave, he was asked what his trade was. He replied that the only trade he knew was that of governing men and therefore, that he wished to be sold to a man who needed a master.

There’s plenty more but these are my favorite. Besides, it’s meant to be a brief description, so I’m keeping it as such.

Why he’s on the list:
The Cynics’ philosophy is to live in agreement with Nature and to become free from the influences of desire such as wealth, power and sex which have no value in Nature.
I always thought this was bullshit and I still do.
However, another one of the Cynics’ principle states that happiness depends on being self-sufficient and a master of mental attitude and for this, I respect them.
Diogenes has been able, throughout his life, to live by those principles and has always shown virtue through actions rather than theory.
But that wouldn’t be enough to make it on this list: this list is for badass people only.
That being said, Diogenes is a critical thinker who doesn’t respect anybody or anything except truth and virtue and those who apply them.
Combine this genuine attitude with the fact that he just doesn’t give a shit about anything and now it makes perfect sense that he’s on this list.

46 — Louis XIV of France

Louis XIV

a.k.a: Le Roi-Soleil

Occupation: King

Born: 1638

Died: 1715

Brief Description:
In 1638, after 23 years of marriage, Anne of Austria finally gave birth to a child, leading contemporaries to regard him as a divine gift and Louis XIV (only the Dauphin at the time) was named Louis-Dieudonne as a consequence. Louis XIII died at the end of the Thirty Years War when his son was only four years old so his mother ruled as regent until her son could claim his throne.
When Louis XIV came into power, France was going through turbulent times and so, he did not live the privileged life of a king-to-be.

In 1660, at the age of 22, Louis married the daughter of King Philip IV of Spain, Marie-Therese, in order to seal the peace treaty after the Thirty Years War. But despite their 6 children and the evidence of affection early on in their marriage, Louis wasn’t devoted to his wife and took many mistresses, both official and unofficial, during his lifetime.
One year later, Cardinal Mazarin, who had been like a father to Louis, died and Louis XIV became King of France. Louis XIV ruled as an absolute monarch of France and involved himself in all matters of state. His statement “L’etat, c’est moi.” is very representative of the way he ran his government.

During Louis’ reign, France fought three majors wars (the Dutch War, the War of the Spanish Succession, the War of the Palatinate) as well as two lesser wars (the War of Devolution and the War of the Reunions) and gained land as a result of these conflicts. But even though France spent most of its years under the reign of Louis XIV fighting wars, it also flourished culturally during these same years. By bringing the Academie Francaise under his patronage, he became its protector, protecting writers such as Moliere, Racine and La Fontaine, whose work remain greatly influential to this day. He also supported music and the visual arts. But perhaps the most spectacular of his achievements remains the Palais de Versailles, which was originally a hunting lodge built by his father and where he eventually relocated his court, thus giving the Louvre to the arts and the public.

He died of gangrene in 1715 after 72 years on the throne. His great-grandson, Louis Duke of Anjou, became his successor (Louis XV) since his son, grandson and eldest great-grandson had all predeceased him.

Why he’s on the list:
Louis XIV put in place the Code Louis, which was later used as a basis for the Napoleonic Code, which itself is still used today as the basis for many modern legal codes. And Napoleon himself, who was anti-Bourbon (Louis XIV was of the House of Bourbon), described him as “the only King of France worthy of the name”.

I love absolute monarchies and I hate democracies. Of course, absolute monarchies are double-edged swords as monarchs can lead their kingdoms to greatness but also to ruin depending on their characters, philosophies and visions. But at least there’s a slight chance it might work. Democracies, on the other hand, never work as politics and personal interests inevitably get in the way of good judgement. I am using democracy here only as a modern example for the other end of the spectrum. In contrast, Louis adhered to the theory of the divine rights of kings, became the most powerful French monarch and consolidated a system of absolute monarchical rule. This, me likey!

But what I like most, even though Louis XIV was often criticized for it, was his vanity. It is said that “there was nothing he liked so much as flattery, or, to put it more plainly, adulation; the coarser and clumsier it was, the more he relished it”. He cultivated his public image and the idealization of the monarch by having himself depicted as Roman Emperors, as Gods and even as Alexander The Great. And if you still don’t think vanity’s cool, just check the Galerie des Glaces at Versailles, it’s enough to understand why he’s on this list.

47 — Lawrence Joseph Ellison

Larry Ellison

a.k.a: The Other Software Billionaire

Occupation: CEO

Born: 1944

Died: Not Yet

Brief Description:
Larry Ellison was born in New York out of wedlock. His mother, judging herself incapable of caring for him, gave him up for adoption to her aunt and uncle.

After graduating from high school, Larry attended the University of Illinois but later dropped out. He then continued his studies at the University of Chicago but dropped out again.

In the 1970s, Larry worked for the Ampex Corporation as a programmer on a database project for the CIA which he named ‘Oracle’.
Soon after, he founded ‘Software Development Laboratories’ (SDL) and subsequently renamed it ‘Relational Software Inc.’ and later ‘Oracle’ after its flagship product ‘Oracle Database’.
The original release was called Oracle 2. There was no Oracle 1.

Although IBM was the primary database system for companies, it did not cater to smaller companies and microcomputers. This allowed Oracle, Sybase and Microsoft to fill in that void.
The original Sybase software was sold to Microsoft and became the well-known SQL Server.
Today, the market is still dominated by IBM, Microsoft and Oracle.

Larry also served for a few years as a director of Apple Computer when Steve Jobs returned to the company in 1997.

He is still the CEO of Oracle and the company keeps on growing…

Why he’s on the list:
As I said in one of my previous posts, I do not like college dropouts but what I like even less are the entrepreneurs who take that hypocritical symbolic $1 salary.
Management and ownership of a company are two very distinct topics and should remain separate. Unlike most entrepreneurs, Larry seems to understand this difference.
Even though he owns more than 20% of Oracle and is ranked by Forbes as the 8th richest person in the world, he also tops the list of the best-paid executive of a public company with total compensations over the past decade reaching well above $1 billion.
It’s like a ‘fuck you’ to the supposedly modest (but hypocritical) CEOs of other successful tech and internet companies whose salary is 1$.
And I like that so I included him on my list.

48 — Robert James Fischer

Bobby Fischer

a.k.a: The Bad Boy of Chess

Occupation: Grandmaster

Born: 1943

Died: 2008

Brief Description:
Bobby Fischer was born in Chicago to a Jewish mother who had moved from Switzerland to the US. The actual identity of his father is unknown. So Bobby grew up with his mother and older sister. When he was six, his sister bought him a chess set and he learned to play from the instructions.

A few years later, Bobby joined the Manhattan Chess Club. At age 13, he defeated the winner of America’s Chess Championship by sacrificing his queen. This game became known as the game of the century. One year later, he won his first US Chess Championship, the first of eight. Later that year, he set the record for becoming the youngest chess Grandmaster.

In 1972, Bobby Fischer played against Boris Spassky for the World Chess Championship title. The game was seen as a proxy battle for the Cold War between the US and the Soviet Union. And although he hated most Soviet players and accused them of collusion, he had respect and affection for Spassky. He ended up winning, thus becoming the first and only American to win the World Chess Championship in the 20th century.

Bobby did not defend his title in 1975 and then disappeared from the chess scene for almost 20 years, after which, he played a rematch against Spassky and won again. This was his last time playing chess in public and only time since his world championship title.
He died of illness at the age of 64, coincidentally the number of squares on a chessboard.

Why he’s on the list:
Bobby Fischer found his passion in chess and went to the extremes to develop his skills.
He read books, analyzed games, and even played against himself because he had no one else to play. He played for the fun, for the challenge, for the love of the game.
Chess was his life.
He loved the imagination and creativity that chess offered and eventually came up with his own chess variant (Chess960) which rendered the memorization of opening moves rather impracticable, thus compelling the players to rely on their talent and creativity instead.
“Let’s play. I’m willing to play anywhere,” says Bobby.

This leads me to my second point. You can’t be so passionate about an activity and so skilled at it and yet remain modest. Modesty is for average people. When you’re consumed by something, you want to prove to yourself and the world that you’re invincible. In Bobby’s words: “I am the best player in the world and I am here to prove it.” It’s a natural consequence of the love of a game rather than mere arrogance, as many tend to think. Provocation is just another way to challenge yourself further, push the limits, be the best, as you’re being put on the spot by those waiting your downfall.

Today, he is still regarded by many to be the best chess player of all time but it’s his love for playing rather than his status that puts him on my list.

49 — Isaac Newton

Isaac Newton

a.k.a: Sir Isaac Newton

Occupation: Scientist

Born: 1642

Died: 1726

Brief Description:
Isaac Newton was born in Woolsthorpe, England. He was the only son of a local farmer who died three months before his birth. When he was three years old, his mother remarried and left him with his grandmother. The lack of his mother’s attention and his hate towards his step-father are believed to have been the cause of his insecurities and paranoia later in life.

In 1661, Newton left for Cambridge University, thus entering a new world, one he could eventually call his own. While at Cambridge, he first got exposed to mathematics and became fascinated by the works of Euclid and Descartes. In the years that followed his bachelor’s degree, Newton made his greatest contribution to mathematics and discovered the law of universal gravitation.

Newton was known for his advancements in mathematics, optics, astronomy as well as mechanics and gravitation. His work ‘Philosophiae Naturalis Principia Mathematica’ is regarded as one of the most important scientific books ever written.

Why he’s on the list:
First of all, Newton never married. Bachelors FTW!
Note: Many people on this list are bachelors but I will not keep on repeating this so keep it in mind…

Especially in the earlier part of his life, Newton was a deeply introverted character and fiercely protective of his privacy and had outbursts of violent temper. Personally, I love introverted people. They’re usually the skilled thinkers and the most interesting to talk to.

Newton graduated from Cambridge without honors. As much as I find successful college dropouts and school failures annoying, I have special affinity for those who actually graduated without any sign of distinction.
Nonetheless, the first hints of Newton’s brilliance could already be found in his boyhood inventions. He created sundials, wooden clocks, water wheels and even a mouse-powered mill.
The result: Newton is generally regarded as the most original and influential theorist in the history of science. And as such, he gets a place on my list.

50 — Alphonse Gabriel Capone

Al Capone

a.k.a: Scarface

Occupation: American Gangster

Born: 1899

Died: 1947

Brief Description:
Al Capone was born in Brooklyn to Italian immigrants and began his career there until he moved to Chicago in his early twenties and became the boss of a criminal organization, the Chicago Outfit.

During the prohibition era, the Outfit amassed great wealth through prostitution, gambling and bootlegging. These funds were used to solidify Capone’s grip on the political and law-enforcement establishments in Chicago and, of course, allowed him to indulge in a luxurious lifestyle.

Although he was never convicted of racketeering charges, Capone was indicted for tax evasion and sentenced to prison but such was his power, that he was still able to run his empire from his cell. After his release in 1939, he returned to his home in Florida but his health had significantly deteriorated due to the syphilis he had contracted in his youth.

Why he’s on the list:
Al Capone went from saloon bouncer to the leading crime boss of Chicago in only six years. He became known worldwide and was admired by many for his disregard of the Prohibition. Today, he has become the stereotype for mobsters, crime lords and criminal masterminds.
And it’s this attitude of absolute power and freedom to act, of doing whatever he wanted because he owned the city, that places him on this list.