Who Was the Funniest Founding Father?

  • Benjamin Franklin, circa 1770
Benjamin Franklin, circa 1770
Credit: © Kean Collection—Archive Photos/Getty Images
Author Kristina Wright

June 15, 2026

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If you picture America’s Founding Fathers as solemn men with stern faces and powdered wigs, you’re getting only half the story. In reality, these figures spent much of their lives writing impassioned letters, arguing politics, insulting rivals, exaggerating grievances, and trying to outwit one another in prose. 

Humor naturally slipped into their writing, sometimes intentionally and sometimes because sarcasm can be easily employed against those who annoy us. Thomas Jefferson once argued that “ridicule is the only weapon which can be used against unintelligible propositions.” 

George Washington, for one, was known to occasionally speak his mind through dry humor. In one instance, he attended a military banquet after the Revolutionary War where elaborate silver cups were presented. After learning that the man who designed the cups had since become a Quaker minister — and knowing that Quakers preferred a plain and simple style that was closer to his own taste — Washington reportedly remarked that he wished the craftsman “had been a Quaker preacher before he made the cups.”

John Adams, meanwhile, had no problem turning his irritations and aggravations into witty insults. Describing Benjamin Franklin in a 1783 letter, Adams complained that Franklin’s “whole life has been one continued insult to good manners and to decency.” 

The jab was meant as criticism, but it also sounds suspiciously like admiration. Because, while many of the founders could occasionally land a sharp line, it was Benjamin Franklin who added humor to nearly everything he wrote.

Credit: © History and Art Collection/Alamy

Ben Franklin’s Mischievous Side

Franklin’s public image often emphasizes the brilliant inventor with the kite, bifocals, and lightning rod. Less attention goes to the fact that he enjoyed provoking people almost as much as he enjoyed experimenting. 

That personality quirk first appeared when he was a young man in Boston, working as an apprentice in his brother’s Boston printing shop. When his brother refused to publish his writing in the newspaper, Franklin invented a fictional middle-aged widow named Mrs. Silence Dogood and slipped essays with her name on them under the door at night so they would be printed.

The Silence Dogood letters were witty and mildly scandalous by colonial standards. In one letter, Mrs. Dogood described Harvard graduates returning home “as great Blockheads as ever, only more proud and self-conceited.” Readers loved the widow’s sharp observations — some men even reportedly proposed marriage to the imaginary woman — and Franklin delighted in using invented characters to say things he could not safely say as himself. 

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