When researching Ted Anthony’s usage of the noun “chestnut” in his articles, I did wonder how “chestnut” could come to mean “An old, frequently repeated joke, story or song” in the first place. The Online Etymology Dictionary speculates it comes from a joke:
Slang sense of “venerable joke or story” is from 1886, probably from a joke (first recorded 1888) based on an oft-repeated story in which a chestnut tree figures. The key part of the 1888 citation is:
[Captain]: When suddenly from the thick boughs of a cork-tree —
[Pablo]: A chestnut, Captain; a chestnut.
[Captain]: Bah! booby, I say a cork-tree!
[Pablo]: A chestnut[.] I should know as well as you, having heard you tell the tale these twenty-seven times.
The interchange between Captain and Pablo felt familiar to me. It reminds me of the Saturday Night Live Skit where Sarah Palin and Hilary Clinton speak out against sexism in campaigns:
Palin: You know, it reminds me of a joke we tell in Alaska.
Clinton: Oh boy.
Palin: What’s the difference…
Palin: Between a hockey mom…
Palin: And a Pitbull?
Clinton: There you go.