This is what happens when the Oracle of Delphi tells you you’re the wisest person in Athens, I guess.
When he told Ion he flat-out sucked at poetry.
Ion was a talented poet who wins first prize in a competition of rhapsodists at the festival of Asclepius, as narrated by Plato. On the road back, he encountered Socrates, and they chatted about Ion and which poets he likes to perform. Ion says he only likes Homer, and then Socrates basically tells him he sucks at life for the rest of the dialogue.
Sickest burn: "No one can fail to see that you speak of Homer without any art or knowledge. If you were able to speak of him by rules of art, you would have been able to speak of all other poets; for poetry is a whole."
(NB: As Socrates didn't leave any of his own writings behind, it's impossible to distinguish the historical Socrates from Socrates as described by Plato et al. These anecdotes are pulled from those writings.)
The time he trolled his students into measuring how far a flea can jump.
In Aristophanes' The Clouds, Socrates got his disciples engaged in a fight about how far a flea could jump. Socrates and Chaerephon then measured an actual flea's foot in wax to see how long it was.
Troll harder: "He said that the gut of the gnat was narrow, and that, in passing through this tiny passage, the air is driven with force toward the breech; then after this slender channel, it encountered the rump, which was distended like a trumpet, and there it resounded sonorously."
When he invented the entire Socratic method.
1. Ask some a question.
2. When they answer, reframe the question in an asshole-y way.
3. Accuse THEM of being an asshole. Repeat.
See: The entire Euthyphro, especially at the end when Euthphyro tries to leave and Socrates is like, "lol come back, I want to piss you off some more."
When he insulted someone and then blamed it on a divine spirit taking over his speech.
In the Phaedrus, Socrates begs Phaedrus to read him a speech by Lysias. Afterward, he remarks that his "daemon" is overtaking him before saying he thought the whole thing was crap.
A sample: "The responsibility rests with you. But hear what follows, and perhaps the fit may be averted; all is in their hands above. I will go on talking to my youth. Listen: [talks for like eight days]."
