Green’s Dictionary of Slang

boss n.2

[Du. baas, master, in which form it first appeared in the American colonies in mid-17C. The term did not arrive in the UK until the mid-19C and has always been sl. or colloq.]

1. [mid-17C+] (also bosshead, bossman) the master (or mistress), the manager, the person in charge.

2. [mid-19C+] (US) an exceptional person; often in context of fashion.

3. [mid-19C+] (orig. US, also bossman) a term of address, esp. to a man whose name one does not know.

4. [late 19C+] a ‘criminal mastermind’.

5. [late 19C] (UK tramp) a farmer, thus boss-crib, farmhouse.

6. [1930s] (UK prison) a prison governor.

7. [1950s] a heroin wholesaler.

8. [1950s+] (US prison) a prison warder.

9. [2000s] (US black) female-to-male fellatio [the dominant role of the male as ‘boss’].

10. (US black) a man.

In compounds

boss-bitch (n.)

[1960s+] (US black) the senior member of a pimp’s ‘stable’ of whores.

boss boy (n.) [S.Afr. derog. boy, an African, usu. a servant or labourer]

[20C+] (S.Afr.) a black foreman or overseer in charge of subordinate black workers.

Boss Charlie (n.) (also …Charley) [generic use of proper name Charlie]

[20C+] (US black) a white man, esp. in authority.

boss cocky (n.) (also boss cockie) [cocky n.2 (2)] [late 19C+]

1. (Aus.) a farmer who employs labour and still works.

2. (Aus.) a person in authority.

boss dog (n.) [20C+]

1. (US) an important person or one who poses as such.

2. (US prison) a prison rapist; one who exploits weaker prisoners, esp. sexually.

boss game (n.)

[1970s] (US black) an important person, usu. in ironic use.

boss lady (n.)

1. [20C+] a female superior.

2. [1910s+] (US, also boss-woman) a wife who dominates her husband.

boss man (n.)

1. [19C] (US) the overseer, foreman, employer, chief prison guard, anyone in authority; also as a term of address.

2. a farmer.

3. [1960s] a pimp.

4. [1970s+] (US gay) the ‘masculine’ member of a homosexual couple.

In phrases

little boss (n.)

[1980s+] (Aus. prison) a middle-level prison officer.

whip boss (n.) [he carries a whip]

[1940s–50s] (US prison) the chief officer on a prison farm.