Josh Billings, Berkshire Funnyman
Updated: Jul 21
by Kelt Wilska
If you asked a Berkshire native who Josh Billings was, odds are that they would respond with, “You mean the race?” After all, the eponymous runaground triathlon is a beloved late-summer fixture here, crossing multiple towns in South County by foot and bike and paddle. But, again, would they know who Josh Billings was? And for that matter, would anyone outside of our small and strangely literary corner of the state even recognize the name? The answer is as wild and unexpected as a race that now lets you traverse the Stockbridge Bowl on a standup paddleboard.
Josh Billings (born Henry Wheeler Shaw, in 1818) was many things, but a cautious homebody he was not. Adventure and mischief called to him from an early age, much to the chagrin of his congressman father, congressman grandfather, and congressman uncle. Shaw tramped the woods and fields of his hometown, Lanesboro and beyond, causing mayhem for neighborhood dogs and churchgoers alike. When the time came for secondary education, his—albeit brief—alma mater was Hamilton College in central New York, where he quickly soured his reputation among professors by stealing the clapper from the historic chapel bell. What happened next lends to the mystery of Shaw’s story. Some say he was expelled. Some say he fully intended to return the next year but was sidetracked on his way back to school by two St. Louis-bound adventurers who he met on an Erie canal boat. Regardless, off to the Midwest it was, where he spent years as a showman, teacher, rancher, and shopkeeper among other occupations.
This jack-of-all trades habit did not stop even when Shaw settled down in Poughkeepsie, New York, with his new bride. Coal miner, farmer, auctioneer…. Only after exploring seemingly every other career did he settle on writing, a craft in which he quickly developed a distinct rhythm and style. His signature creation was a folksy take on the aphorism, that short and pithy piece of wit once distributed in phrasebooks (when phrasebooks were a thing). Ever heard the saying “Love is like measles...the later in life it occurs, the tougher it gets”? This is attributed to Shaw. His sudden rise to fame, though, came from an odd linguistic experiment. “Humin natur is the same all over the world, cept in New England, and that its akordin to sarkumstances.” “Truth is mitey and will prevail; so iz cider mitey, but yu hav got tew tap the barrel before it will prevale.” Misspelling almost every word, combining country slang with worldly wisdom acquired through his many adventures, Shaw had created a name for himself, and in more ways than one. In choosing the pseudonym Josh Billings, he was joining the ranks of his American humorist contemporaries, among whom it was popular to embrace another name.
While Billings’ work was said to have brought a chuckle to Abraham Lincoln, he never did reach the heights of his peer, Mark Twain. Why is this? Why did Billings fade into the past? Was Twain just…funnier? Was his humor more timeless? Perhaps by leaning heavily into the language gimmicks, Billings lost his chance at leaving a more significant mark on the American literary consciousness. Maybe, though, lasting fame was never his intention. A quick laugh, and on to the next joke, on to the next phrase. The motto of the Josh Billings runaground race embodies this sentiment by reusing an apt Billings quote: “to finish is to win.” To write and make someone smile is to succeed.