Green’s Dictionary of Slang

asshole n.

[ass n. (2) + SE hole/hole n.1 (1); see also arsehole n.]

1. [mid-19C+] the anus.

2. [mid-19C+] the least appetizing, poorest, most run-down and poss. dangerous area of a city or town or place.

3. [1930s+] a fool, a derog. description of a subject.

4. [1970s+] a general term of address.

5. see asshole buddy

In derivatives

ass-holer (n.)

[1980s] a sodomite, thus a male homosexual.

assholiness (n.)

the quality of being a fool or otherwise socially unacceptable individual.

assholeish (adj.)

[1980s+] (US) unpleasant, poss. deliberately so.

In compounds

asshole bandit (n.) [1950s+]

1. [1960s] (US) a Greek (immigrant).

2. (US gay) an anilinguist.

3. (US gay) in anal intercourse, the active partner; thus used derog. for a predatory homosexual male.

4. (US) a derog. term for a male homosexual (cf. arsehole bandit under arsehole n.).

asshole-breath (n.)

[1960s+] a term of contempt.

asshole buddy (n.) [buddy n.]

1. [1940s+] (also A-hole buddy, asshole) an extremely close friend.

2. [1950s+] (US gay) a normally heterosexual man who, deprived for whatever reason of women, enjoys anal intercourse, whether as an active or passive partner.

asshole tight (adj.)

extremely intimate.

In phrases

break out into assholes (v.)

[1970s+] (US) to become terrified.

fall through one’s own asshole (v.)

[1960s–70s] (US) to be extremely surprised, utterly shocked.

from asshole to appetite (also from asshole to Adam’s apple)

[1940s] (US) thoroughly, absolutely, totally.

have an asshole of (v.)

[1920s–50s] (US black) to have a great deal of something.

have a paper asshole (v.) [1940s+]

1. (US) orig milit., to be a weakling, to be a coward.

2. (also have a paper ass) to talk excessively, esp. when meaningless; usu. talk like you have a paper ass(hole).

3. to do anything excessively.

keep a tight asshole (v.) (also keep a tight hole) [the propensity of intense fear to loosen one’s bowels]

[1940s+] (orig. US milit.) to maintain emotional control.

lock assholes (v.) (also lock, lock asses)

[1950s+] (US) to fight.

not know one’s asshole from one’s piehole (v.)

[2000s] (US) to be stupid.

out the asshole (adv.) [i.e. fig. excrement]

[1960s+] (US) a general intensifier, blatantly, excessively, totally, reprehensibly, in large quantities.

snap assholes (v.)

[1950s+] (US) to fight.

think one’s asshole squirts perfume (v.)

[1940s+] (US) to have a high (but unjustifiable) view of one’s own abilities.

up to one’s asshole

[1970s+] involved to the greatest extent.