Socrates

"To express oneself badly is not only faulty as far as the language goes, but does some harm to the soul."

—Socrates (attributed)

Socrates, commonly considered the father of philosophy, was an Athenian philosopher who lived from 469-399 BCE, when he was executed in the wake of the Peloponnesian War (of which, interestingly, he was a veteran, having served with distinction at Delium in an earlier phase of the war). Despite his reputation, he was not, by any stretch, the first philosopher -- earlier philosophers certainly existed and are, in fact, known as the "pre-Socratic philosophers".

He disapproved of writing, and so is known chiefly through the writings of his student Plato. (Another of his students, Xenophon, also wrote about him, but his works are less known.) Socrates taught and inspired many prominent young Athenians, from the aforementioned Plato to Alcibiades. (Plato even devoted a good chunk of his Symposium to defending against the common charge that Socrates had an affair with Alcibiades).

The story goes that the Oracle at Delphi described Socrates as the wisest man in Greece, and Socrates, a simple bricklayer, set out to disprove this claim by seeking out all the most knowledgeable men in Greece and demonstrating that they knew more than he did. It always backfired, because Socrates, possessing basic reasoning skills, could always see and point out the massive holes in everyone's claims. For example, he tried to get Euthyphro, an esteemed religious expert, to put forth a workable definition of "piety". None of Euthyphro's attempts held up under scrutiny, and eventually he gave up and went away.

Take everything you read about Socrates with a grain of salt: Plato was very fond of putting his own words in his teacher's mouth, and it's hard to tell how much of Socrates's dialogue in Plato's works are Socrates's words and how much are Plato's. (This is described academically as the "Socratic problem".) The Apology (Plato) is usually considered the most faithful work, and it covers Socrates's trial and conviction on charges of corrupting the youth and introducing new gods. If one reads between the lines in Republic and Symposium, it's quite possible that Socrates was guilty on both counts, though he vigorously denied the charges in court. Aristophanes lambasted him without mercy in The Clouds.

Socrates provides examples of the following tropes:

Armor-Piercing Question: His specialty.
Badass Beard
Bald of Awesome
Beauty Equals Goodness: In a time when many Greeks genuinely believed this (good looks could allegedly even be used as exonerating evidence in court), Socrates was a major aversion.
Compliment Backfire: Some people just can't take a compliment...
Constantly Curious
Cool and Unusual Punishment: He doesn't get one, but if there is an afterlife, he IS one - interrogating the dead about their wisdom.
Cool Old Guy
Cultured Badass: He was a hoplite which means he was expected to charge straight into a hedgehog-thick row of spears. And at the Battle of Delium he became a war hero by organizing an orderly retreat when the rest of the Athenian army were running helter-skelter
The Cynic/Deadpan Snarker: So much. He was even an immediate influence to the original Greek Cynics.
Does Not Like Shoes: Possibly the Ur Example.
Doomed Moral Victor
Dying Moment of Awesome/Obi-Wan Moment: His trial and execution.
Face Death with Dignity
The Gadfly: Trope Namer. Some semantic drift.
Genius Bruiser: Although not as much as his student Plato (who was a pankration champion), Socrates did serve with distinction in the Peloponnesian War, which took no small amount of physical strength.
I Drank What: Implied in the film Real Genius - which is the Trope Namer here - and in other comedies that Socrates accidentally drank the hemlock. But this is averted in Real Life: Socrates knew exactly what he was doing.
I Love You Because I Can't Control You: Apparently why Socrates married Xanthippe.
New Media Are Evil: Socrates did not approve of reading. He thought it destroyed the memory.
- Well, on a person-by-person basis, he was right. It's just that having decentralized physical memory such as books allows for a greater possible total sum of human knowledge.
  - A benefit he probably never considered. The enormous benefits of writing were probably hard for the ancients to conceive, especially Socrates, who came to the conclusion that no one really knew anything anyways.
Obfuscating Stupidity: Combine this with Armor-Piercing Question and you've got the Socratic method.
The Philosopher/Contemplate Our Navels: Obviously, but he's not the sesquipedalian, "bookish" philosopher.
Suicide by Cop: What his execution might have been; according to Plato's The Crito, Socrates went willingly to his sentence to teach others the value of law in a just society.
Teacher-Student Romance: With Plato. Much Values Dissonance ensues for modern readers, such as that the Ancient Greeks had six different kinds of love, each identified with a separate word, and Teacher-Student Romance was effectively one of them.
Word of Dante: Plato is the intercessory agent here.