The tortoise and the playwright - 458 B.C.
The possibly apocryphal but widely-disseminated story of Aeschylus' death goes something like this: the legendary Greek playwright was walking outside when an eagle, mistaking his round bald head for a rock, dropped a tortoise on it. (Seriously.) Apparently, eagles still use this technique to break open shelled prey -- no word as to whether the tortoise was killed as well as the writer.
The stoic who died laughing - 207 B.C.
It's said that the Greek philosopher Chrysippus died of laughter while watching his drunken donkey attempt to eat figs. (Actually, if he'd had a video camera, sounds like that might've been the first great YouTube phenomenon. Which, if everyone were as sensitive to funny animal videos as the Greeks probably would've been, could lead to a doomsday scenario like this.)
The man who thought too much - 270 B.C.
The Greek poet and philosopher Philitas of Cos is said to have died from insomnia while contemplating the Liar Paradox. (An example of a Liar: "The next sentence is false. The previous sentence is true.") According to Athenaeus, his epitaph read:
"Philetas of Cos am I
'Twas The Liar who made me die,
And the bad nights caused thereby."
The man with the golden tongue - 53 B.C.
Roman general and politician Marcus Licinius Crassus was one of the most rich and powerful men of his time. He suppressed the slave rebellion led by Spartacus and boasted a number of impressive military victories won under his command. Still hankering for glory, however, he led a disastrous military campaign into Syria, and was executed after an embarrassing defeat at Carrhae. It is rumored that he died in one of two -- equally bizarre -- ways: either by having molten gold poured down his throat (supposedly to satisfy his unquenchable thirst for wealth) or by having his head used as a theatrical prop by enemy king Orodes II. Either way, he makes our list with flying colors.