Green’s Dictionary of Slang

chestnut n.

[the term emerged c.1880 but appears to have originated in the play Broken Sword (1816) by W. Dimond. The relevant passage reads: ‘Zavior: When suddenly from the thick boughs of a cork tree. Pablo: (Jumping up.) A chestnut, Captain, a chestnut. Captain, this is the twenty-seventh time I have heard you relate this story, and you invariably said, a chestnut, till now’]
(orig. US)

1. an old, much-repeated joke that has long-since lost any real humour.

Larens Advertiser (SC) 9 Dec. 1/1: The increase of the chestnut joke is truly significant.
Springfield Daily Republic (OH) 15 Sept. 1/3: The audience groaned at the buff-coloured jokes and antedeluvian chestnuts gotten off by the company.
[Aus]Dead Bird (Sydney) 21 Sept. 6/2: This is a hoary-headed back blocks chestnut.
[UK]Sporting Times 4 Jan. 6: There they are cracking their chestnuts like one o’clock.
[US]Nat. Police Gaz. (NY) 22 Feb. 2/3: [I]f they told a chestnut he couldn’t move and kick hia tormentors out.
[Aus]Truth (Sydney) 28 Jan. 1/3: The story about the fortunate gentleman who ate somebody else’s dinner [...] was a chestnut when New South Wales was started.
[Aus]Bulletin (Sydney) 14 Apr. 15/4: That ‘marry-the-girl’ yarn is a world-wide chestnut.
[UK]D. Cotsford Society Snapshots 220: The Author (re-roasting a ‘chestnut’). People ought to be willing to rehearse for that!
[US]‘Hugh McHugh’ Skidoo! 107: The best stuffing for turkeys is chestnuts, which you can obtain from any author who writes musical comedy.
[US]T.A. Dorgan Silk Hat Harry’s Divorce Suit 9 Oct. [synd. cartoon strip] ‘Did you hear the story about the fellow who bought the parrot that could speak seven languages?’ ‘Aw. That’s the last word in chestnuts. Columbus told that one to his sailors’.
[US]‘Phinneas A. Crutch’ Queen of Sheba 165: balkis: It’s a peach. You’ll never guess it. psha: Chestnut, you mean.
[US]D. Maurer Big Con 252: The old gold brick game, a chestnut, if ever there was one.
[US]Green & Laurie Show Biz from Vaude to Video 5: Actors laid them in the aisles with such sparkling chestnuts as ...
[US]Wentworth & Flexner DAS.
[US]T. Robinson Rough Trade [ebook] ‘Oh, that old chestnut. What do you call a musician without a girlfriend?’ ‘Homeless’.

2. any anecdote (not necessarily true) or dictum that is often repeated.

[US]Nat. Police Gaz. (NY) 2 Oct. 14/3: It's always the same old chestnut, ‘Boston came too late,’ and the public has to stand the same weakness year after year.
[UK]Sporting Times 8 Mar. 1/4: ‘I overbalanced and fell on the hot grate, just as I was pulling out some chestnuts—’ ‘What, for the paper?’ interrupted Arthur and the atmosphere was full of office rulers.
[Aus]Sun. Times (Perth) 23 Apr. 4/7: Writer came into the office [...] to prepare his weekly budget of chestnuts [etc.].
[UK]Sporting Times 25 Mar. 13/3: Now-a-days black or brown hair suffering from old age is like a story afflicted with the same complaint. It becomes a chestnut.
[UK]Sporting Times 1 Jan. 10/3: Only one story was worth remembering among the baked chesnuts that the orators showered on us.
[US]Hecht & MacArthur Front Page Act I: We’ve been printing that chestnut for weeks!
[UK]H.E. Bates My Uncle Silas 69: Uncle Silas brought out the chestnut of how a game keeper had blown his hat off with a double-barrelled gun.
[Aus]D. Stivens Jimmy Brockett 69: The stories about him grew—many of them apocryphal, no doubt, some of them chestnuts.
[UK]N. Cohn Awopbop. (1970) 224: It was the oldest chestnut imaginable.
[NZ](con. 1930s) H. Anderson Men of the Milford Road 150: Somebody then asked if there was anybody else who could tell a new story — they didn’t want any old chestnuts they had heard before.
[US]S. Morgan Homeboy 5: The old chestnut [...] about when she was a kid and ran away with the circus.
[UK]Guardian Guide 5–11 Feb. 69: Liberally dispensing such chestnuts of paranoid thought as ‘Information is power – power is control’.
[US]J. Stahl OG Dad xiv: Here’s a chestnut: if you’re tired of thinking about yourself, have a child.

3. anything once popular, now hackneyed and unfashionable.

[US]D.K. Ranous Diary of a Daly Débutante (1910) 199: Think of doing that awful old Nancy Lee—such a chestnut! [...] and following it up with that happy, romping dance!
[US] ‘High School Sl.’ in N.Y. Dispatch 31 May 7: I wish you wouldn’t say ‘take the belt,’ Floy. Don’t you know that’s a regular chestnut, and none of the girls in our gang use it any more.
[UK]Sporting Times 1 Feb. 1/5: In conclusion, ‘May the best men win!’ (Yah! Get out! What are you giving us? Rats! Chestnuts! It’s been said before!).
[US]Ade More Fables in Sl. (1960) 173: He knew they [i.e. certain old songs] were Chestnuts, and had been called in, but they suited him.
[US]Van Loan ‘The Pitch-Out’ in Lucky Seventh (2004) 287: Sings all those old chestnuts that always get a hand somehow.
[US]A. Hazzard Mother Liked It in Hatch & Hamalian Lost Plays of Harlem Renaissance (1996) 64: His stunts were all chestnuts.
[US]F. Swados House of Fury (1959) 84: They all knew the rules were old chestnuts, dusted off every time a girl ran away.
[UK]J. Cary Horse’s Mouth (1948) 62: ‘Well, how’s the revolution?’ ‘Revolution.’ He spat on the kerb. ‘That chestnut. Are you trying to be funny, or is it a joke?’.
[US]A. Maupin Further Tales of the City (1984) 23: The movies were [...] comfy old chestnuts like Splendor in the Grass.

4. a scheme, a trick.

[Aus]Bulletin (Sydney) 5 July 8/1: In fact the ways of arranging the matter are numberless, and yet with all these unbounded resources at command, the Australian keeps on leaving his hat and boots on the sea-shore, and as a consequence when his widow applies for the money the manager of the [insurance] company simply gets mad at the monotony of the old chestnut and throws her indignantly into the street.

In compounds

chestnut picket (n.)

(US) undefined term pertaining to commercial sex.

[US]N.E. Police Gaz. (Boston, MA) 12 Oct. 5/2: Annie and Em, two charitable creatures of 178 Canal street, are ‘some’ on ‘chestnut pickers’ (The meaning of the above item will be explained to the uninitiated upon application at this office).

In exclamations

chestnut!

(US) excl. of dismissal, mockery.

[US]Nat. Police Gaz. (NY) 30 Oct. 7/2: ‘'Oh, chestnut,'’ responded the dude spokesman, ‘you can’t crawl out of it so easy as that. We know you aud show our utter contempt for you’.