Philip Stanhope, the 4th Earl of Chesterfield (born 22 September 1694) wrote to his illegitimate son Philip (a diplomat) a famous series of ‘Letters to His Son on the Art of Becoming a Man of the World and a Gentleman’ (1774) (https://tinyurl.com/y7l3xfl8), published posthumously by Philip Jr.’s widow.

Why Lord Chesterfield’s letters are famous: Lord Chesterfield is arguably the greatest paragon of eloquent hoighty-toightiness in English letters, a sort of English Castiglione. But his life story is also like a biblical parable (or Greek tragedy) showing the perils of *fathering way too hard.*

Lord Chesterfield wrote letters to Philip from the age of 5 to when Philip died (to his father’s shock) at age 36. The letters were the means by which Lord Chesterfield sought to mold Philip–morally, but far more so, *socially*, in manners–into a more perfect version of himself. (As my Twitter follower @adavidsouthard observes, this is “a familiar parental endeavor.”)

But Philip could never be quite perfect enough to meet the stringent demands of his father; he lacked the social grace to carry off the advice he was given. And the advice Lord Chesterfield offers in these letters (which Chesterfield never intended to be published) is … how shall we say it? … extremely practical (read: cynical.)

The advice is less about how to be a good person (not that Chesterfield actively counseled Philip to be a bad person–with the exception of the infamous Letter 202, the hilarious upshot of which is Adultery with Rich Men’s Wives = Good!) but more about how to advance in the world, like a very eloquently phrased, 18th century version of How to Win Friends and Influence People. See for example this excerpt on why it’s good to flatter people’s vanities and how to go about doing it:

It’s not for nothing that Samuel Johnson said the letters “teach the morals of a whore, and the manners of a dancing-master.” (There is also a hilarious anecdote about how Johnson, while feuding with Chesterfield, called him “the proudest man this day”–not a compliment–to which someone rejoined that there was at least one man more arrogant than Chesterfield in England, Johnson himself.)

Fun fact: Chesterfield popularized (but didn’t invent) the phrase “manners maketh man,” which you may recall from the 2014 movie Kingsman: The Secret Service.