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)]

a sodomite.

[UK]Grose Classical Dict. of the Vulgar Tongue n.p.: Usher, or gentleman of the back door. The same [i.e. as prev. entry backgammon n.].
[UK]Lex. Balatronicum.
[UK]‘Jon Bee’ Dict. of the Turf, the Ring, the Chase, etc. 5: Backgammoner or Back-doors man or gentleman ― a fellow whose propensities lie out of the natural order of things in England.
[UK]E. de la Bédollière Londres et les Anglais 312/2: gentleman of the back-door, [...] Intraduisible.
[UK]Farmer Vocabula Amatoria (1966) 15: Apôtre de l’anus, m. A sodomite; ‘an usher of the back-door’.
gentleman of the brush (n.)

an artist, a painter.

[UK]Egan Life in London (1869) 185: This term [...] had given great offence to several gentlemen of the brush.
gentleman of the counter (n.)

a shop clerk.

[UK]Paul Pry 29 Jan. 1/2: [A] common ‘dancing shop,’ frequented principally by gentlemen of the counter, fighting men, and a great many Jews.
gentleman of the drop (n.)

(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.

[UK]G. Parker Life’s Painter 177: Gentlemen of the drop. Are a set of people to be seen in all the great thorough-fares of London [...] They dress quite different, some like farmers and graziers, with a drab coat, a brown two curl wig, boots, spurs, &c., others like walking jockeys, horse-dealers, tradesmen, gentlemen, mackaronies, &c. Some speak Irish, some Welch, and others the West and North Country dialects; they often appear as raw countrymen.
gentleman of the matt and feather (n.)

(US) an aficionado of cock-fighting.

Indep. Journal (N.Y.) 31 Jan. 2/2: Several meetings of the gentlemen of the matt and feather have lately been held in this city, which produced much sport in the gallant pastime of cock-fighting.
gentleman of the pad (n.) [pad n.1 (1)]

1. a highwayman.

Farquhar Beaux’ Stratagem II ii: D’ye know of any other Gentlemen o’ the Pad on this Road?
[UK]T. Walker The Quaker’s Opera III ii: There’s Shepherd and Miss Frisky, both as fine as Five-pence; and Four or Five more Gentlemen of the Pad.
[UK]C. Johnson Hist. of Highwaymen &c. 139: ’Tis that makes Gentlemen of the Pad, as I am, wear a Tyburn Tippet, or old Storey’s Cap on some Country Gallows. [Ibid.] 311: A Law that was soon pass’d in Scotland, for the hanging of a Highwayman as soon as ever he was taken. This Statute was afterwards often put in Force against Gentlemen of the Pad.
[UK]W. Scott Rob Roy (1883) 81: Gentlemen of the pad, as they were then termed.

2. a street-robber.

[UK]Partridge DSUE (8th edn) 846/2: ca. 1820–50.
gentleman of the road (n.)

1. a highwayman.

Ordinary’s Account 9 Nov. 5: He bad a Hackney Coach stand, behind Buckingham House; there was a Gentleman and Lady in the Coach; the Gentleman he commanded to come into the Road to him out of the Coach, upon which, the Lady very briskly told him, tho' he was a Gentleman of the Road, she knew the Way of the Town as well as he, for he knew little of the Town to attack such as she. [...] [Then] he thrust up his Pistol, and swore he’d thrust it in her Face and bolt out her Eyes.
[UK]B.H. Malkin (trans.) Adventures of Gil Blas (1822) I 40: I do not think you are fool enough to make any bones about consorting with gentlemen of the road.
[UK]Lytton Paul Clifford II 108: Gentlemen of the Road, the Street, the Theatre and the Shop! Prigs, Toby-men, and Squires of the Cross!
[UK]Duncombe Dens of London 37: Jamie [...] was, however, a professed gentleman of the road; had an eye as sleepy and cunning as a cat.
[UK]J. Lindridge Sixteen-String Jack 151: I’m a gemman of the road — damme!
[US]H.B. Marriott-Watson in New Rev. 8 July n.p.: But if a gentleman of the road must be hindered by the impudent accidents of the weather, he had best ... settle down with empty pockets afore a mercer’s counter [F&H].

2. (also man of the road) a tramp.

[UK]Shields Dly Gaz. 11 June 4/4: The gentleman of the road! Thus our modern rhymsters [...] speak of the tramp.
D. Runyon ‘A Tale of Two Fists’ IV in Pittsburgh Press (PA) Financial Sect. 20 Apr. 6/1: Any person who has had any experience [...] with the gentlemen of the road can tell that Dempsey has been about a bit.
[US]N. Anderson Hobo 6: The women and children of the neighborhood are usually outnumbered by the men of the road, who monopolize the benches and crowd the shady places.
[US]Monteleone Criminal Sl. (rev. edn).
[US]H. Ellison Introduction in Pulling a Train’ [ebook] Sleeping under railroad trestles, shating gypsy coffee out of a tin can with ‘gentlemen of the road’.
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’]

a discharged or invalided soldier who makes his living by begging.

[UK]Jonson Every Man In his Humour III ii: He had so written himself into the habit of one of your poor Disparview’s here, your decayed, ruinous, worm-eaten gentlemen of the round.
gentleman of the short staff (n.) [his truncheon]

a constable.

[UK](con. 1703) W.H. Ainsworth Jack Sheppard (1840) 21: That (in the language of the gentleman of the short staff) an important caption could be effected.
gentleman of the swag (n.)

see under swag n.1

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

a punning phr.: see cit. 1788.

[UK]Grose Classical Dict. of the Vulgar Tongue ms. additions n.p.: Gentleman of Three Ins. In Debt, in Gaol, & in danger of remaining there for Life: or, in Gaol, Indicted, & in danger of being hanged in Chains.
[UK]Grose Classical Dict. of the Vulgar Tongue (2nd, 3rd edn).
[UK]Lex. Balatronicum.
[UK]Egan Grose’s Classical Dict. of the Vulgar Tongue.
[UK]Hotten Sl. Dict. 142: ‘GENTLEMAN OF THE THREE INNS’ — that is, in debt, in a danger, and in poverty.
[US]A.J. Pollock Und. Speaks 44/2: Gent of 3 ins, in debt; in danger; in poverty.
gentleman of three outs (n.) (also gentleman of (the) four outs, gentleman with three outs) [for vars. see cits. 1830 and 1864]

a punning phr.: see cit. 1785.

[UK]Grose Classical Dict. of the Vulgar Tongue n.p.: Gentleman of Three Outs. That is, without money, without wit, and without manners: some add another out, i.e. without credit.
[UK]Lex. Balatronicum.
[UK]Egan Grose’s Classical Dict. of the Vulgar Tongue.
[UK]Lytton Paul Clifford I 64: In a very short period, we grieve to say, Paul became that distinguished character, a gentleman of three outs, – ‘out of pocket, out of elbows, and out of credit.’.
[UK](con. 1737–9) W.H. Ainsworth Rookwood (1857) 170: Jerry Juniper was what the classical Captain Grose would designate a ‘gentleman with three outs;’ and, although he was not entirely without wit, nor, his associates avouched, without money, nor, certainly, in his own opinion, had that been asked, without manners; yet was he assuredly without shoes, without stockings, without shirt.
[US]Flash (N.Y.) 31 Oct. 3/3: To sum up, he wears a moustache, which is the only manly thing about him, and is a gentleman with three outs – out of wit, money and manners.
[UK]Hotten Sl. Dict. 142: ‘GENTLEMAN OF FOUR OUTS’ — ‘that is, without wit, without money, without credit, and without manners.’.
[UK]Farmer & Henley Sl. and Its Analogues.