It is hard to find a philosopher who writes well. One can list the good stylists on one hand: Bernard Williams, for the clear frankness of his prose; Stanley Cavell, whose writing self-reflectively folds in on itself like origami; Friedrich Nietzsche, whose dazzle and exclamation seduce many people into questionable ideas. David Hume is typically seen as part of this crowd. The 18th-century Scottish philosopher wrote in many genres: not only essays, dissertations and treatises, but dialogues, impersonated monologues and biographies. Hume adored the literary celebrities of his day, like the essayist Joseph Addison, who founded The Spectator magazine, and the French moralist Jean de La Bruyère. He was also unfailingly committed to finding a way to bridge the divide between scholars and society, between a world that was ‘learned’ and one that was ‘conversible’. However, it was Hume who helped to divide what we now call ‘literature’ from what we now call ‘philosophy’. He did so by posing a devastating challenge to the prestige of one literary tool that had long been considered a legitimate method in which to practise philosophy: the character sketch.

Characters and Caricaturas (1743) by William Hogarth. Courtesy the Met Museum, New York

What is a character sketch? It is a short description of a person, a social type, which focuses on their habitual preferences and behaviours. Imagine describing a type of person: an incel, an intellectual, a mansplainer. You might start by saying that they are ‘the kind of person who…’ The incel is a kind of person who lives in their parents’ basement, who knows the latest memes, and who politically probably leans far Right, or at least libertarian. The intellectual is the kind of person who likes good coffee shops, reads high-brow magazines, and who politically finds themselves leaning liberal, or far Left. The mansplainer, to borrow the journalist Marin Cogan’s memorable expression, is the kind of person who has a ‘need to explain to you – with the overly simplistic, patient tone of an elementary school teacher – really obvious shit you already knew.’

The character sketch is a genre that is descriptive by nature, and that today reads as a little sociological, a little literary, and more than a little comic. While a part of our everyday discourse, this genre has a long history, stretching all the way back to ancient Greece. Over the course of this history, the character sketch became entangled with another discipline entirely: moral philosophy, the branch of philosophy concerned with virtues and vices, with thinking about social customs and mores, and altogether with trying to work out what it takes to become good. For hundreds of years, the character sketch was understood as a standard method of practising this form of philosophy – until Hume challenged this assumption in 1748. With this, philosophy and literature started to split.

The ancient Greek thinker who should be credited with establishing this curious form of writing is a little-known philosopher called Theophrastus, who sits within the canon of great philosophical stylists. His name, given to him late in life by his teacher Aristotle, means ‘divine speaker’. (He was formerly called Euphrastus or ‘good speaker’ but then he got upgraded.) Theophrastus directed his writerly talents to a dizzying range of topics. He wrote treatises on juice, as well as works of metaphysics, logic and politics. He is most renowned, however, for two things: inventing the science of botany, and writing a very short book that came to be known as the Characters.

The Characters is a collection that sets out to define 30 vices. It does so by writing sketches of types who embody these qualities. In the Characters, Theophrastus considers vices like Bad Timing, Absentmindedness, and Idle Chatter, and then shows them in action. The Man with Bad Timing, for example, is someone who always chooses the wrong moment. He ‘is the sort who goes up to someone who is busy and asks his advice,’ who ‘sings love songs to his girlfriend when she has a fever,’ who, ‘when a man has just returned from a long journey,’ invites him to go for a walk. The Absentminded man is similarly maladroit. He is the sort of person who, when he’s in the audience at the theatre, ‘falls asleep and is left behind alone.’

The Characters was a ‘guide’ to understanding what kind of people you should frequent and what kind to avoid

As these examples hint, Theophrastus is not interested in glamorous vices, vices that make tragedies, vices that present clear problems like Envy or Lust. The qualities he depicts are linked together by the special quality of being ordinary: these are social sins that we commit at the scale of the everyday. Theophrastus’ vices are not only everyday, but they are explored without an eye to explanation. At no point does Theophrastus indicate why the Man with Bad Timing behaves as he does. These sketches are works of description alone.

Theophrastus’ short work, with its interest in describing ordinary kinds of ineptitude, has long puzzled classicists, who have battled over why Theophrastus wrote it. Was this a work of rhetoric, helping young lawyers work out how to mock defendants in court? Was it an appendix to the Poetics, listing comic characters, as opposed to the tragic characters favoured by Aristotle? Or was it a work of ethics: exposing a set of bad qualities one should keep in check, when living among other people? The first person to attempt to answer this question was an anonymous Roman writer, who decided to write a spurious preface to the text in Theophrastus’ name. The Characters, the preface claims, has two ambitions. It is an exercise in classifying and describing people, in the same way that Theophrastus had previously classified plants. And, it is a work with a significant ethical intention. The Characters should be used as a ‘guide’, this preface says, to understanding what kind of people you should frequent, and what kind you should avoid.

This preface launched a moral reading of the Characters, which proved incredibly popular in the Renaissance.

In a European intellectual society racing to recover ancient manuscripts, and to use ancient wisdom to solve modern problems, Theophrastus’ Characters was a big hit. After it was first translated into Latin in the 1430s (by an Italian man who was looking to impress a Paduan Papal chamberlain), humanist after humanist rushed in to offer new and improved Latin translations, complete with explanations of what........

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