Green’s Dictionary of Slang

asshole adj.

[asshole n.]

1. [1930s+] (US) a general negative description, unpleasant, worthless, obnoxious etc.

2. [2000s] of a place, run-down.

3. stupid.

In derivatives

assholingest (adj.)

[1970s] (US) the notional superlative of sense 1 above.