The legend of Democritus the laughing philosopher, alone or in juxtaposition with his counterpart Heraclitus the weeping philosopher, first appears as an anecdote (chreia) in Imperial age philosophers and poets, but has gone on to influence literature and visual arts down to the present day. An examination of its sources reveals interesting discussions of a frustrating mess of emotions: laughing and weeping, anger and tranquility. Melancholy is not an emotion but a disease or character disposition, one which is the apparent cause of all of these symptoms of manic depression (to speak anachronistically). In this chapter, I discuss the ancient influences on the anecdote coming from the writings of Heraclitus of Ephesus (flourished circa 500 BCE), Democritus of Abdera (born circa 460 BCE), and from a classical account of melancholy attributed to Aristotle.