Green’s Dictionary of Slang

1. (US, also assholey) a general negative description, unpleasant, worthless, obnoxious etc.

1957		T.T. Chamales Never So Few (1958) 182: You’re an asshole moralist.
1962		(con. 1940s) G. Mandel Wax Boom 84: A high and mighty face don’t fool you none, and an ass-hole voice is just plain shit.
1969		N. Spinrad Bug Jack Barron 22: So what if Jack has asshole reasons.
1975		N. De Mille Smack Man (1991) 51: Some kinda asshole tough guy.
1982		G.V. Higgins Patriot Game (1985) 225: Not like your asshole brother.
1994		T. Willocks Green River Rising 78: Devlin didn’t want to be seen as some asshole outsider.
2007		W. Ellis Crooked Little Vein 98: My asshole boyfriend’s in San Antone.
2000		Guardian Rev. 14 Jan. 2: I was always playing the [...] asshole lawyer or the doctor.
2010		K. Richards Life 312: Most guys I know are assholes, I have some great asshole friends.
2011		J.J. DeCeglie Drawing Dead [ebook] This guy she was talking about, this asshole loser, I can’t say I hated him.
2012		J. Dicker Harry Quebert Affair (2015) 223: Write this down, Mr Asshole Writer.
2012		M. Lacher On the Bro’d 7: I thought Derek was sorta like a lessy assholey The Situation — ripped, funny as shit, with spiked hair.
2019		D. Winslow Border [ebook] ‘Just be your normal asshole self’.
2020		C. Hiaasen Squeeze Me 256: ‘I liked how you dealt with the asshole fawn poacher’.

2. of a place, run-down.

2003

N. Green Angel of Montague Street (2004) 29: Drag me all the way [...] to the asshole end of Brooklyn.

3. stupid.

2011

J.J. DeCeglie Drawing Dead [ebook] I wasn’t about to take any asshole chances.