Green’s Dictionary of Slang

Old Harry n.

[give old Harry is still current in W.I. use; Nares, Glossary (1822), defines the phr. as ‘formerly applied satirically to Henry the Eighth’]

1. (also Lord Harry, old Henry) the Devil.

[UK]Mercurius Fumigosus 13 23–30 Aug. 121: If Plaisterers must marry, before their dead Wifes cold, / ’Tis pitty (by Old Harry) but they should be Cuckold.
[Ire]K. O’Hara Midas II i: I swear by Old Harry The moment madam’s coffin’d – Her I’ll marry.
[Ire]J. O’Keeffe Wicklow Mountains 40: This is surely old harry calling this wicked fellow to him.
[UK]J. Poole Hamlet Travestie I i: I’ll speak to it, should e’en Old Harry dare me.
[US]R. Waln Hermit in America on Visit to Phila. 2nd series 24: ‘An elegant six’—‘All luck, by old Harry’.
[UK] ‘The Turncock’ in Regular Thing, And No Mistake 68: Sam swore he loved, she swore again, / ‘blow her if she’d marry’, / He thought to blow his brains out / straight, and toddle to old Harry.
[UK]Talfourd & Seymour Sir Rupert, the Fearless I v: Nor send us all straight to Old Harry.
[UK]Western Times 8 Nov. 5/5: Old Harry and the Dragon came to be consigned to the flames.
[UK]Leaves from Diary of Celebrated Burglar 106/2: As soon as a ‘poke’ was ‘brought off’ and ‘slung,’ the ‘stall’ who ‘copped’ it [...] ‘namased’ like as if the old ’Arry was after him.
[US]A. Pinkerton Reminiscences 24: Everything is going to the old Harry while I am playing detective!
[US](con. c.1840) ‘Mark Twain’ Huckleberry Finn 360: I lay I’ll tan the Old Harry out o’ both o’ ye!
[Aus]H. Lawson ‘Word to Texas Jack’ in Roderick (1967–9) I 65: Texas Jack you are amusin’. Great Lord Harry how I laughed.
[US]‘Frederick Benton Williams’ (H.E. Hamblen) On Many Seas 268: Then indeed there was the Old Harry to pay [...] they hopped right up and down with rage.
[US]Ade More Fables in Sl. (1960) 97: You’re just full of the old Harry.
[US]O.O. McIntyre Bits of New York Life 17 Dec. [synd. col.] Then in our bourgeosie [sic] way we were all full of the Old Harry.
[US]E. Dahlberg Bottom Dogs 36: The girls in the shop said they would make a dandy match, just her size, short, blond, blue eyes, full of old Harry in ’em.
[US]D. Runyon ‘It Comes Up Mud’ Runyon on Broadway (1954) 546: He is pretty sure it is old Henry Devil himself.
[UK]D. Bolster Roll On My Twelve 128: We’ve dropped the old hook, it’s good old Harry flatters and a make-and-mend.
[UK]C. Harris Three-Ha’Pence to the Angel 41: But George, ’e’s got the cheek of Old ’Arry.
[US]H. Rawson Dict. of Invective (1991) 277: Old Nick. One of many old nicknames for the devil, e.g., the Old Gentleman, Old Harry, Old Roger, and Old Scratch.

2. a form of unspecified adulterant used in wine.

[UK]B.E. Dict. Canting Crew n.p.: Old Harry, a Composition used by Vintners, when they bedevil their Wines.
[UK]Grose Classical Dict. of the Vulgar Tongue.
[UK]Lex. Balatronicum.
[UK]Egan Grose’s Classical Dict. of the Vulgar Tongue.

In phrases

like old Harry (adv.)

to a great (lit. ‘devilish’) extent.

[US]R. Carlton New Purchase I 176: I gits bodaciously sker’d and hollows agin like the very ole Harry.
[US](con. 1916) G. Swarthout Tin Lizzie Troop (1978) 165: We fought like the old Harry.
play old Harry (with) (v.) (also give old Harry)

to ‘play the Devil’ (with), to make mischief, to tease or scold.

[UK]G. Colman Yngr John Bull II iii: Heigh! they are playing up old Harry below!
[UK]Annals of Sporting 1 Mar. 210/1: ‘Psha! Psha! cried the Squire; is it old Harry you’d play, Master Div**?’.
[UK]Hotten Dict. of Modern Sl. etc. (2nd edn) 153: ‘To play old harry with one,’ i.e., ruin or annoy him.
[Aus]Illawarra Mercury (Wollongong, NSW) 18 Sept. 2/1: [A] pugilist who has sprained his knuckles is said [...] to have ‘smashed his bunch of fives,’ [...] to have ‘spiflicated his flipper,’ or ‘played old Harry with his mawley’.
[US]S.P. Boyer diary 28 Apr. in Barnes Naval Surgeon (1963) 176: The canned lobster will play ‘Old Harry’ with his bowels.
[UK]‘Old Calabar’ Won in a Canter I 278: ‘I had played old Harry with my fortune, and it would not have lasted long at the rate I was going’.
[Aus]Bulletin (Sydney) 28 Mar. 11/1: When the squatters of an infested district were buying cats of the Thomas variety and letting them loose to play old Harry with poor little bunny, the professional rabbiters killed and skinned these same cats, docked the tails short, and sold the skins mixed up with the rabbit skins, to the deluded owners for 3d. each.
[UK]J. Astley Fifty Years (2nd edn) II 34: With a good bank I could play ‘old Harry’ with the management.
[US]Omaha Dly Bee (NE) 28 Jan. 2/5: He thought he was playing the old Harry with the opposite side.
[UK]Boy’s Own Paper 3 Aug. 694: I could have brought a couple of small ironclads [...] and played ‘Old Harry’ with the Russian army.
[UK]‘Taffrail’ Pincher Martin 226: If this pile of wood catches fire it’ll play Old Harry on the upper-deck with the twelve pounders and their ammunition.
[Aus]Advertiser (Adelaide) 20 Jan. 11/7: He played old Harry with the furniture.