Green’s Dictionary of Slang

1. (US) a tramp, a migrant worker; also attrib.

[1894		Mirror of Life 25 Aug. 2/4: Hungry Higgins: ‘Dat’s a mighty short but you are smokin.’ Weary Watkins: ‘I know it, but I don’t have to draw the smoke so far, see?’].
1900		Bulletin (Sydney) 15 Dec. 10/3: Recently saw half-a-dozen rats lying in front of the Richmond Town-hall. Evidently had been purchased by the council, which thus stood a good chance of being double-banked by any passing Weary Willie. And if those rats were infected, they certainly gave the plague a grand chance of spreading, for every wandering cur mauled them about, and inquiring small boys took them up and examined them minutely.
1904		Sun. Times (Perth) 10 Jan. 8/3: [headline] Weary Willie Wires. Six Hours To Go 80 Miles.
1906		L.A. Herald 17 June 40/1: Four-Footed Weary Willies. This is the time of year when the two-legged tramp leaves the jail [...] In just the same way the town rats will soon be moving.
1908		Truth (Wellington) 11 Jan. 5/6: [headline] Where Weary Willie Wants for Nothing. the swaggie’s supper.
1910		Derbys. Advertiser 2 Dec. 25/4: Miles away from Derby, I have heard its casual ward described by many ‘Weary Willies’ as a “’ard un”’.
1912		Bulletin (Sydney) 25 July 14/2: [T]he experienced Australian bushman won’t have the fresh immigrant, partly for the reasons that restrain Fat and Co. from taking Weary Willie into partnership in their large and prosperous city business, and partly because the experienced bushman objects to having an inexperienced mug from Fogville-on-Thames dropping trees on him when his attention is otherwise engaged.
1916		‘A-No. 1’ Snare of the Road 19: I saw the Weary Willie coming back on a run to where I was waiting.
1922		E. Dyson Missing Link 🌐 Ch. iii: A fellah ’d think you’d just come from sleeping in a rubbish bin. Yes. Best Weary Willie I’ve seen.
1922		B. Hecht A Thousand and One Afternoons [ebook] ‘My wardrobe is practically gone.’ He glanced with apparent amusement at his weary-willie makeup.
1923		N. Anderson Hobo 157: I told him I was a college student looking for work. ‘The hell you are!’ he sneered, ‘you’re a Weary Willie, now get out of here.’.
1933		Hecht & Fowler Great Magoo 61: Despite the somewhat weary-willie ensemble, he is a forceful-speaking fellow.
1942		W. Winchell On Broadway 3 Feb. [synd. col.] Victor Killian as the weary willie and Pat Hitchcock as his little chum.
1949		Monteleone Criminal Sl. (rev. edn).

2. ? a prison warden.

1904

Sun. Times (Perth) 10 Jan. 1/1: That a Perth detective warned the Weary Willie in charge of a prisoner's gaol breaking proclivities.