Green’s Dictionary of Slang

(US) an ageing, impoverished, poss. alcoholic tramp who frequents low drinking saloons.

1890–1904		Farmer & Henley Sl. and Its Analogues I 135/1: Barrel-boarder, subs. (American) – A loafer in low drinking-saloons.
1909		W.H. Davies Beggars 47: The sole occupation of a barrel-house stiff is to stand outside public-houses waiting for invitations to drink [...] There is not often more than one or two barrel stiffs to one house.
1926		W.H. Davies Adventures of Johnny Walker 56: The barrel-house-stiff is the most despised of all stiffs, for the simple reason that he is a physical wreck [...] The barrel-house-stiff is the shortest liver of all stiffs.
1927		‘Jargon of the Und.’ in DN V 438: Barrel-dosser, The lowest order of bums who sleep in and live upon the offal of barrel-houses. Also barrel-stiff.
1931		Irwin Amer. Tramp and Und. Sl. 22: Barrel Dosser. [Ibid.] 23: Barrel Stiff.—An old, worn-out bum, living in barrel houses, eating whatever may be salvaged from garbage cans or cheap lunch rooms, and absolutely without hope or ambition.
1949		Monteleone Criminal Sl. (rev. edn) 17: barrel dosser A tramp who frequents barrel houses [...] barrel stiff A low-class tramp who frequents barrel houses.
1962		Ragen & Finston World’s Toughest Prison 790: barrel-stiff An old worn out bum living in barrelhouses.