Two old, two new, and please don’t mention sprite colour limitations.
The courier waits as Descartes composes a letter to Princess Elisabeth.
Not a very philosophical emphasis, I admit; but Super Mario/Übermensch jokes would have been too obvious.
I settled on Asellus/Beauvoir partly because of the implied gender ambiguity in Asellus’s story, and partly because arguably it also has existential themes.
I imagine Socrates provoked facial expressions like those when questioning people. In retrospect, though, Diogenes would have been much more fitting...