Green’s Dictionary of Slang

1. an Italian, spec. an immigrant [the domination of the occupation by Italians].

[1891		in Punch CI:31 Oct. 208: Podb. (overhearing this, with horror): [...] I say, for goodness’ sake, don’t let’s have that old organ-grinding Johnny in the coupé with us! [...] the Italian Gentleman [...] is unceremoniously bundled by the Conductor into the hinder part of the diligence].
c.1940		Heroes in Bold (1979) 108: The Duce gives the order / To fight against the foe / And off to darkest Africa / the organ-grinders go.
1945		‘Song from ‘London Diary’’ in Mess Songs & Rhymes of the RAAF 35: [as 1940].

2. (US) a sexually active male [SE organ + grind v. (1)].

1928		Victoria Spivey ‘Organ Grinder Blues’ 🎵 It’s not your organ / But the way you grind / Organ grinder organ grinder.
1928		C. Williams ‘Organ Grinder Blues’ 🎵 Organ grinder, organ grinder, organ grinder play that melody / Take your organ and grind some more for me / Grind it north, grind it north / grind it north, and grind it east and west / When you grind it slow, I like it the best.
1954		in Randolph & Legman Ozark Folksongs and Folklore (1992) II 592: When I was young, my damfool luck, / All the maidens I did fuck; / Fucked ’em all, an’ knocked ’em up, / With my little organ grinder.
c.1960		in E. Cray Erotic Muse (1992) 342: Straight from the whorehouse, pecker like steel, / My little organ grinder.

3. a senior figure, an authority [phr. talk to the organ-grinder, not the monkey].

2007

S. Low Boys from Baghdad 228: The following morning, I sent an email to my boss in Baghdad—straight to the organ-grinder .