Green’s Dictionary of Slang

gentleman of... n.

In phrases

gentleman of the back door (n.) (also back-doors gentleman, usher of the back door) [back-door n. (1)]

[late 18C–19C] a sodomite.

gentleman of the brush (n.)

[early 19C] an artist, a painter.

gentleman of the counter (n.)

[mid-19C] a shop clerk.

gentleman of the drop (n.)

[late 18C] (UK Und.) a confidence trickster who preys on naïve countrymen, persuading them that they can win money by playing cards with a supposedly drunk person – who of course is a confederate.

gentleman of the matt and feather (n.)

[late 18C] (US) an aficionado of cock-fighting.

gentleman of the pad (n.) [pad n.1 (1)]

1. [18C] a highwayman.

2. [early–mid-19C] a street-robber.

gentleman of the road (n.)

1. [18-19C] a highwayman.

2. [1900s–50s] (also man of the road) a tramp.

gentleman of the round (n.) [play on SE gentleman of the round, ‘a gentleman soldier, but of low rank [...] whose office it was to visit and inspect the sentinels, watches, and advanced guard. It was, therefore, an office of some trust, though little dignity’ (Nares, Glossary, 1822) + pun on one who ‘does the rounds’]

[late 16C–early 17C] a discharged or invalided soldier who makes his living by begging.

gentleman of the scamp (n.)

[late 18C] a highwayman; a thief.

gentleman of the short staff (n.) [his truncheon]

[mid-19C] a constable.

gentleman of the swag (n.)

see under swag n.1

gentleman of (the) three ins (n.) (also gentleman of the three inns)

[late 18C] ‘In debt, in gaol, and in danger of remaining there for life; or, in gaol, indicted and in danger of being hanged in chains’ (Grose, 1788).

gentleman of three outs (n.) (also gentleman of (the) four outs, gentleman with three outs) [vars. include ‘out of pocket, out of elbows, and out of credit’ (Bulwer-Lytton, Paul Clifford, 1830); ... of the four outs, ‘without wit, without money, without credit and without manners’ (Hotten, 1864)]

[late 18C–19C] ‘Without money, without wit, and without manners; some add another out, i.e. without credit’ (Grose, 1785).