Green’s Dictionary of Slang

asshole adj.

[asshole n.]

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

[US]T.T. Chamales Never So Few (1958) 182: You’re an asshole moralist.
[US](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.
[US]N. Spinrad Bug Jack Barron 22: So what if Jack has asshole reasons.
[US]N. De Mille Smack Man (1991) 51: Some kinda asshole tough guy.
[US]G.V. Higgins Patriot Game (1985) 225: Not like your asshole brother.
[US]T. Willocks Green River Rising 78: Devlin didn’t want to be seen as some asshole outsider.
[US]W. Ellis Crooked Little Vein 98: My asshole boyfriend’s in San Antone.
[UK]Guardian Rev. 14 Jan. 2: I was always playing the [...] asshole lawyer or the doctor.
[UK]K. Richards Life 312: Most guys I know are assholes, I have some great asshole friends.
[Aus]J.J. DeCeglie Drawing Dead [ebook] This guy she was talking about, this asshole loser, I can’t say I hated him.
[US]J. Dicker Harry Quebert Affair (2015) 223: Write this down, Mr Asshole Writer.

2. of a place, run-down.

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

3. stupid.

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

In derivatives

assholingest (adj.)

(US) the notional superlative of sense 1 above.

[US]D. Ponicsan Cinderella Liberty 76: That’s about the assholingest excuse I ever heard.