In scouring my email to recover old newsletters, I came across two readers who wrote in to recommend this story to me — Drew P. in 2012 and Eric L. in 2016. So, yeah, this one is long overdue. Thanks to both of you for suggesting. And if anyone else has a story idea, send it along — it may take me a decade, but I’ll get there! — Dan

Most of us have wondered, at some point, what people would say at our funeral. Who would show up, who would cry, and who would tell the story we'd rather they didn't. It's a morbid little thought experiment, but a harmless one, because there's no way to ever find out. The guest of honor, after all, isn't in a position to listen. You'll just have to trust that it went well.

Unless, of course, you hold the funeral early.

Timothy Dexter was born in Malden, Massachusetts, in 1747, and he did not start out with much. Per the New England Historical Society, he was working as an indentured farm servant by age eight, later apprenticed as a leather dresser, and eventually landed in the port town of Newburyport. There he married a widow named Elizabeth Frothingham and "set up shop in the basement of his wife's house, selling moosehide trousers, gloves, hides and blubber." He saved up a few thousand dollars and put it into Continental currency, the paper money of the Revolution, which by then was worth next to nothing. Then the new federal government made good on that debt, and, as American Heritage put it, "Dexter overnight became a man of substance." Legends about his luck piled up from there: he supposedly shipped coal to the coal town of Newcastle and sold cats to the Caribbean. According to his first biographer, Samuel L. Knapp, local merchants once tricked him into sending a load of bed-warming pans to the tropical West Indies, where a clever ship captain resold them to sugar makers as ladles.

Money bought Dexter a lot of things, but it didn't buy him the respect of Newburyport's old families, so he went looking for attention instead. He gave himself the title "Lord." He bought a mansion and filled the grounds with more than 40 painted wooden statues of great men — Washington, Jefferson, Napoleon, and, per Atlas Obscura, Dexter himself, above an inscription calling him "the greatest philosopher in the Western world." He wrote a book, A Pickle for the Knowing Ones, with creative spelling and no punctuation at all. When readers complained, he added a page of punctuation marks to the second edition so they could "peper and solt it as they plese." He was weird — but he was also very famous, and, it turns out, kind of insecure, and wanted people to cosplay as if he were dead. You know, so people would cry on his behalf and recount how awesome he was.

Dexter built himself a tomb in the basement of a summer house on his property, bright and airy, because if a candle keeps away bad dreams, daylight should keep away "ugly spectres" too. He hunted down choice mahogany for his coffin, hired a real cabinetmaker to build it, added four silver handles, and climbed in to make sure it fit. He kept it on display for visitors. And ultimately, he took it out for a test drive. He gave his wife, son, and daughter "suits of mourning and money to boot" to play along, and sent out invitations. No clergyman would officiate, so a friend read the burial service and delivered a eulogy for "the great man of the East." The coffin went into the vault, the door was locked, and the mourners went back to the house, where "the choicest wines were poured out like water."

Then a loud complaint came from the kitchen.

It was Dexter, very much alive, beating his wife with a cane. He'd been hiding upstairs enjoying the praise, and he'd noticed that she didn't cry. As Knapp put it: "She had not shed a tear! She should have cried to think it was not a reality." An 1886 account quoted by Atlas Obscura says he was "satisfied with all except that his wife did not shed so many tears as he thought were becoming." His son, on the other hand, performed admirably, according to Knapp, "being sufficiently drunk to weep without much effort." Dexter then joined his own wake, drank the wine, and threw coins out the window to the boys gathered outside. His only other complaint was that "not a single bell tolled." Modern retellings often say 3,000 people came, but Knapp gives no number. He says only that the invited guests showed up, along with "all who desired a frolic."

Dexter died for real on October 26, 1806. All that planning didn't help much. By order of the town's Board of Health, he wasn't placed in his well-lit tomb at all. As Historic Ipswich notes, he was buried in the town's Hill cemetery, under what Find a Grave describes as "a simple tombstone that gives no hint of the colorful character who lies beneath it." No word on whether the bells rang that time.

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Today’s Bonus fact: In 1915, a South Carolina woman named Essie Dunbar had an epileptic seizure and died, so her community held a funeral for her and buried her body. Dunbar’s sister, who lived rather far away, arrived late to the service — Essie’s coffin was almost entirely buried before the sister arrived. The sister insisted on seeing Essie one last time and demanded that the body be exhumed. She was successful, and it’s a good thing, too. As Mental Floss explained, Essie’s seizure wasn’t fatal: “When the coffin lid was opened, Essie sat up and smiled at all around her. She lived for another 47 years.”

From the Archives: How to Make Sure People Attend Your Funeral: You can rent a grieving friend.

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And thanks! — Dan