If a joke or expression works, especially for a comic or a public speaker, it is usually overused and is consequently called “an old chestnut.”
The expression comes from a British play, The Broken Sword, or The Torrent of the Valley, written by William Dimond (1780-1837) and first produced in 1816 at London’s Royal Covent Garden Theater.
Within that play a principal character continually repeats the same joke about a cork tree, each time with a subtle variation, including changing the tree from cork to chestnut.
Finally, tiring of the joke, another character, Pablo, says: “A chestnut! I’ve heard you tell that joke twenty-seven times and I’m sure it was a chestnut!”
The impact moment when the phrase likely entered the English language was during a dinner party somewhat later in the nineteenth century.
At the dinner the American actor William Warren the Younger (1812-1888), who at the time was playing the part of Pablo, used the “chestnut line” from the play to interrupt a guest who had begun to repeat an old familiar joke.
Coincidentally perhaps, the younger Warren’s father, also named William, was an actor, too, who for a time was associated with Philadelphia’s Chestnut Street Theater.