Green’s Dictionary of Slang

1. the devil.

1890–1904

Farmer & Henley Sl. and Its Analogues.

2. a boss, a manager, a police sergeant or captain etc.

[1796		Grose Classical Dict. of the Vulgar Tongue (3rd edn) n.p.: Skipper [...] the captain of a Dutch vessel.].
1864, 1867, 1870		Hotten Sl. Dict.
1877		H. Hartigan Stray Leaves (1st ser.) 178: Rather shame-faced was Larry as he faced the ‘skipper,’ [i.e. army captain] as we used to call him.
1889		H. Smart Long Odds II 214: ‘If I understand Jack Cuxwold — and I know my dear old skipper pretty well — he sees his way into fooling old Mohammed some’.
1900		‘Doss Chiderdoss’ ‘Follow My Leader’ Sporting Times 27 Oct. 1/4: The Britons who seafaring go / Can at spinning a yarn take the palm; / And the skipper can tell ’em to rights, as you know, / So I follow the captain, marm!
1906		A.H. Lewis Confessions of a Detective 14: The skipper wants to look you over.
1915		Atlanta Constitution 29 Aug. 42/2: I got the goods on you all right. Come on over and see the ‘skipper’ (captain).
1916		J. Lait ‘“Taxi, Mister!”’ in Beef, Iron and Wine (1917) 141: All this is preliminary to the tale of Marty Taylor, skipper of a numbered, registered, polished taxicab.
1929		A.J. Barr Let Tomorrow Come 23: The jailer ambles past. Gordon calls to him, ‘Say, skipper, is May still in stir – that dame that bumped Bates?’.
1938		F.D. Sharpe Sharpe of the Flying Squad 58: He reported to the sergeant: ‘All correct, skipper’.
1943		‘Henry Green’ Caught (2001) 90: You’ve said it skipper.
1958		(con. 1950) E. Frankel Band of Brothers 3: We already got the best skipper in the division – as good a marine as ever took a dump between a pair of boondockers.
1968		G. Radano Walking the Beat 185: ‘He’s so sanctimonious! But that didn’t keep him from bumping our old skipper out of the precinct so he could get the job’ .
1975		J. Wambaugh Choirboys (1976) 19: He blinked and said ‘Hi Skipper’ to Captain Drobeck.
1987		(con. 1967) E. Spencer Welcome to Vietnam (1989) 29: Me, the new skipper who now commands seasoned platoon commanders.
1990		(con. c.1970) G. Hasford Phantom Blooper 29: The skipper was one hell of a decent man. He was people, you son of a bitch.
2003		H. Hill A Good Fella’s Guide To N.Y. 8: The Capos are the middlemen, sometimes called skippers.
2010		(con. 1973) C. Stella Johnny Porno 39: Eddie Vento, who happened to be a skipper with the Vignieri crime family.
2024		C. Stella Joey Piss Pot 4: ‘Jerry Galante is acting skipper for Montalvo’s crew’.

3. a general mode of address.

1895		Shields Dly Gaz. 18 Apr. n.p.: ‘Well, well, skipper,’ said the Sheriff good-naturedly, ‘for a’ that the loons would hae been nane the waur o’ their kail’.
1927		C. Coe Me – Gangster 161: I don’t mean to be fresh, skipper.
1935		H. McCoy They Shoot Horses, Don’t They? (UK edn only) 154: ‘Say a word, skipper – ’ Rocky said, tilting the microphone stand over.
1946		(con. 1910s) J. Thompson Heed the Thunder (1994) 144: Havin’ yourself a time there, skipper?
1951		D. Stivens Jimmy Brockett 182: ‘Where do you want to go, skipper?’ I asked him. ‘Where the horses are, daddy.’.
1990		(con. early 1950s) J. Ellroy L.A. Confidential 340: Skipper, you should sit down, you look like you’re about to have a coronary.
1992		V. Headley Yardie 19: Skipper, any phone box around here.
2000		Indep. on Sun. 9 Jan. 26: Must dash, skipper, bye!
2017		V. McDermid Insidious Intent (2018) 29: ‘Morning, skipper [...] shall I make us all a brew?’.
2024		J. Meades Empty Wigs (t/s) 940: ‘I’d like to be delivering top griff Skipper but, you know, fucking zilch is fucking zilch’.

4. see captain n. (13)