Green’s Dictionary of Slang

(orig. US) a dispute, a quarrel, a problem, a nuisance, anything requiring irritating effort.

1945		Down Beat 15 Feb. 1: Building bands is getting to be a habit with Freddie Slack. He broke up his last few after booking hassels but is currently planning another.
1946		in Sat. Eve. Post 31 Aug. 72: ‘Hassle’ is a gorgeously descriptive word which lately has won usage in show business. It means a quarrel, a fuss, an argument, a struggle or a mess.
1950		N. Cassady letter in Charters (1993) 202: I’d only be a little late returning to Joan, where I’d plead hassel in getting the clothes.
1951		J. Blake letter 18 Mar. in Joint (1972) 16: Being away from [...] all that sex hassle, has done wonders for my peace of mind and serenity.
1959		Mad mag. Sept. 41: Now we’re real hung up in a crazy big hassle.
1960		‘Lord Buckley’ Hiparama of the Classics 15: We have stomped out here to the hassel site of some of the worst Jazz Blowin’ in the entire issue.
1967		E. Shepard Doom Pussy 65: You’re a mighty snazzy chicken to be hanging your fanny out coverin’ this cockeyed hassle.
1971		Current Sl. VI 6: Hass, n. A bother, a nuisance.
1975		E. Torres Carlito’s Way 56: Any beef or hassle come up, kill right away.
1977		E. Bunker Animal Factory 121: If he gets in a hassel, T.J. and Bad Eye would go berserk.
1986		R.G. Barrett Real Thing 175: Would you smoke it outside the car [...] Saves me a hassle.
1989		T. Blacker Fixx 123: The alleged ‘rip-offs’ and ‘legal hassles’.
1991		R.G. Barrett Between the Devlin 46: ‘What’s the hassle man?’.
1996		P. Howard The Joy (2015) [ebook] The Hulk’s getting a bit of hassle from a couple of the screws.
1999		N. Cohn Yes We have No 286: He’d got into a hassle with Mal Platt.
2000		Indep. on Sun. Real Life 16 Jan. 9: Without all the hassle of having to meet them somewhere miles from home.
2004		R.G. Barrett Rosa Marie’s Baby (2013) [ebook] There were no hassles about having to eat.
2012		M. Lacher On the Bro’d 176: [M]y dad knew a dude who could get me into UC-Boulder without a bunch of hassle.
2015		I. Welsh Decent Ride 35: Drug dealin is a big risk and a load ay hassle for no much reward.
2017		L. McInerney Blood Miracles : ‘Selling it [ii.e. a piano] would be hassle’.
2021		Breen & Conlon Hitmen 224: ‘[G]iving out about women [...] giving out about partners giving them hassle’.