The weekend newspapers are full of them. Our computer screens are full of them. They go by different names—columns, opinion pieces, diaries, blogs—but personal essays are alive and well in the twenty-first century. They flourish just as they did in James Thurber’s and E. B. White’s twentieth-century New York, or in the nineteenth-century London of William Hazlitt and Charles Lamb. There seems no end to the appeal of the essayist’s basic idea: that you can write spontaneously and ramblingly about yourself and your interests, and that the world will love you for it.

No end—but there was a beginning. The essay tradition blossomed in English-speaking countries only after being invented by a sixteenth-century Frenchman, Michel Eyquem de Montaigne. His contemporary, the English writer Francis Bacon, also used the title Essays, but his were well-organized intellectual inquiries. While Bacon was assembling his thoughts neatly, the self-avowedly lazy nobleman and winegrower Montaigne was letting his run riot on the other side of the Channel. In his Essais (“Attempts”), published in 1580 and later expanded into larger editions, he wrote as if he were chatting to his readers: just two friends, whiling away an afternoon in conversation.

Montaigne raised questions rather than giving answers. He wrote about whatever caught his eye: war, psychology, animals, sex, magic, diplomacy, vanity, glory, violence, hermaphroditism, self-doubt. Most of all, he wrote about himself and was amazed at the variety he found within. “I cannot keep my subject still,” he said. “It goes along befuddled and staggering, with a natural drunkenness.” His writing followed the same wayward path.

In doing this, he rejected almost every literary virtue the French were to hold dear for the next few hundred years: clarity, rigour, beauty, and elegance. Yet his rebellious style gave him immense appeal to British, Irish and American authors. For more than 450 years, they took inspiration from Montaigne and his meandering charms.

One of the first was William Shakespeare. A whole monologue of The Tempest—that in which Gonzalo conjures up an ideal society in a state of nature—seems cribbed from John Florio’s translation of the Essais, published in 1603 but circulated earlier in manuscript. “No kind of traffic / Would I admit,” says Gonzalo; “no name of magistrate; / Letters should not be known; riches, poverty, / And use of service, none.” Florio’s Montaigne talks about a state with “no kind of traffike, no knowledge of Letters, no intelligence of numbers, no name of magistrate, nor of politike superioritie; no use of service, of riches or of povertie.” It was not just the words that sounded similar: Shakespeare and Montaigne both held up an attractive dream of an innocent utopia, while clearly doubting its practicability.

It’s possible that Shakespeare also borrowed a little of Montaigne’s character when working on Hamlet. Like the prince, Montaigne thought too much and was haunted by his own inconsistency and indecisiveness. “We are, I know not how, double within ourselves,” he wrote. “We are all patchwork, and so shapeless and diverse in composition that each bit, each moment, plays its own game.” He even observed that brooding on all the consequences of actions makes it impossible to do anything—exactly Hamlet’s problem.

While French literature became ever more poised and formal, seventeenth-century England produced a series of oddballs very like Montaigne, often paying him explicit tribute: writers such as Robert Burton, whose Anatomy of Melancholy ran about “like a ranging spaniel, that barks at every bird he sees,” or Sir Thomas Browne, who wrote in tangled prose about doctors, gardens, burial urns, and imaginary libraries. In subsequent centuries, more and more English writers belonged to what the critic Walter Pater called “the true family of Montaigne.” They had “that intimacy, that modern subjectivity, which may be called the Montaignesque element in literature.” You can see it in Oliver Goldsmith, Alexander Pope, John Dryden, and even the pompously classical Samuel Johnson, whose Rambler essays have the most Montaignesque title imaginable.

The rambliest of all was the Anglo-Irishman Laurence Sterne, whose digressive novel Tristram Shandy several times mentions the Essays—which seems positively well-ordered by comparison. Tristram’s supposed plot vanishes, and all its elements appear out of order, with the Author’s Preface turning up in chapter 20 of volume 3. The rest is governed by whim and play. “Have I not promised the world a chapter of knots?” Sterne asks at one point; “two chapters upon the right and the wrong end of a woman? a chapter upon whiskers? a chapter upon wishes?—a chapter of noses?—No, I have done that:—a chapter upon my uncle Toby’s modesty: to say nothing of a chapter upon chapters, which I will finish before I sleep.” The knots unravel and the wishes remain unfulfilled; we never reach any destination, for limitless distractions intrude along the way. As Montaigne remarked about his own year traveling in Italy, no one could have said he failed to follow an itinerary, for he only had one simple plan: to keep moving and to see interesting things. So long as he was doing this, he was adhering closely to the program.

“In taking up his pen,” wrote the great essayist William Hazlitt of Montaigne, “he did not set up for a philosopher, wit, orator, or moralist, but he became all these by merely daring to tell us whatever passed through his mind.” He wrote about things as they are, not things as they should be—and this included himself. He communicated his being on the page, as it changed from moment to moment; we can all recognize parts of ourselves in the portrait.

In America, Ralph Waldo Emerson felt this shock of familiarity the first time he picked up Montaigne in his father’s library. “It seemed to me as if I had myself written the book, in some former life, so sincerely it spoke my thought and experience,” he wrote. “No book before or since was ever so much to me as that.” From Renaissance winegrower to nineteenth-century transcendentalist seems a big leap, yet Emerson could hardly tell where he ended and Montaigne began.

These days, the Montaignean willingness to follow thoughts where they lead, and to look for communication and reflections between people, emerges in Anglophone writers from Joan Didion to Jonathan Franzen, from Annie Dillard to David Sedaris. And it flourishes most of all online, where writers reflect on their experience with more brio and experimentalism than ever before.

Bloggers might be surprised to hear that they are keeping alive a tradition created more than four centuries ago. Montaigne, in turn, might not have expected to be remembered so long, least of all in the English language—yet he always believed that such understanding between remote eras and cultures was possible. “Each man bears the entire form of the human condition,” he said. We are united in the very fact of our diversity, and “this great world is the mirror in which we must look at ourselves to recognize ourselves from the proper angle.” His book is such a world, and when we look into it there is no end to the strangeness and familiarity we might see.

Sarah Bakewell is the author of How To Live: A Life of Montaigne in One Question and Twenty-One Answers.