Green’s Dictionary of Slang

(US) $1; in pl., money.

1883		Davenport (IA) Gazette 26 June n.p.: [...] unto Mr. and did offer to him many fat SIMOLEONS and talents of gold.
1885		Ledger (Noblesville, IN) 14 Aug. 6/2: ‘I expect a stiff today with a “samoleon” or two’.
1886		Lantern (N.O.) 13 Oct. 2: The Judge [...] invited the poor fellow [...] to contribute twenty-five sambolios to the city’s correction fund.
1889		A Bates Philistines 180: ‘Princeton platinum [....] It is a dream that people buy pieces of for good hard samoleons, and--’ ‘Good what?’ interrupted the country member. ‘Shekels, dollars, for cash under whatever name you choose to give it.’.
1890		St Paul Globe (MN) 17 Nov. 3/2: A soldier’s life [...] is all right in its way, but the jingle of simoleons in their pockets is better.
1896		Ade Artie 63: He said I could have it for four hundred samoleons.
1902		Ade Forty Modern Fables 122: I ran it up to an even Hundred Samoleons so that you would not have to bother with any Small Change.
1902		Boston Globe Sun. Mag. 21 Dec. 7–8: A man who has money has ‘bullets’ or ‘plunks’ or ‘simoleons.’.
1902		‘Hugh McHugh’ It’s Up to You 68: Through the kindly assistance of a bell-boy and a few simoleums we were piloted across the hotel to another elevator.
1907		C.E. Mulford Bar-20 iv: If yu wants to corral this here herd of simoleons yu has to ride a cayuse what Red bet me yu can’t ride.
1908		B. Fisher A. Mutt in Blackbeard Compilation (1977) 157: The wad is now 458 hard simoleons.
1909		J.W. Carr in ‘Word-List From Northwest Arkansas’ in DN III:v 404: simloons, the, n. Money.
1910		‘O. Henry’ ‘Strictly Business’ in Strictly Business (1915) 9: I live on it and put a few simoleons every week under the loose brick in the old kitchen hearth.
1915		Wodehouse Psmith Journalist (1993) 265: So when de rent-guy blows in, who’s to slip him over de simoleons? [Ibid.] 335: An uncle of mine some years ago left me a considerable number of simoleons.
1918		L.E. Ruggles Navy Explained 102: Sailormen [...] probably coin more words for money than any other body of men [...] Sheckles, iron men, washers, clackers, jack, cart wheels, simoleons, kopex, mazuma, palm grease, evil metal, oro, jingles, liberty, bait, sou, armor, plate, holy stones, joy berries, and many others.
1920		Ade Hand-made Fables 173: Claude was counting the Leaves in his new Check-Book and trying to grapple with and encompass the Stupendous Fact that he had One Hundred Thousand gleaming Simoleons.
1925		S. Lewis Arrowsmith 86: Father deftly removed the sum of six simolea.
1927		W. Edge Main Stem 106: A coupla more days like ’at an’ I’ll draw about a hundred twenty-five simoleons for two weeks’ work — clear.
1935		C.E. Mulford ‘Don’t Frame a Red Head’ in Western Fiction Monthly Aug. n.p.: Sixty-two bucks, three score an’ two simoleons; all I’ve got.
1939		Howsley Argot: Dict. of Und. Sl.
1946		Mezzrow & Wolfe Really the Blues 140: The ones who stayed devoted and single-minded and never got dazzled by the Almighty Simolion.
1949		L. Hughes Tambourines to Glory I vi: laura: Table stakes? buddy.: Say, fifty simoleons.
1955		R. Graziano Somebody Up There Likes Me (1956) 132: I figure seventy simoleons for a total of ten minutes work is not too bad.
1975		L. Rosten Dear ‘Herm’ 120: I bet you will stash away 1,000,000 bucks (or ‘simoleons’ as we used to say at old Crane Tech.).
1983		‘Heat Moon’ Blue Highways 191: I heard girls at the Big Four are getting twenty-five simoleons for a straight.
1991		C. Hiaasen Native Tongue 229: Two million simoleons outta my goddamn pocket.
1997–2001		Online Sl. Dict. 🌐 samolean n 1. a unit of money. Notes: also spelled ‘samolian’.
1998		R.G. Barrett Goodoo Goodoo 4: If he was interested it was his for a hundred simoleans.
2002		Scott Phillips Walkaway (2003) 237: Waking up wih the screaming meamies and knowing you turned down ten simoleons.
2005		J. Stahl I, Fatty 123: Zukor presented a cool 100,000 simoleons to the [...] DA.
2015		Orlando Sentinal (FL) 23 Dec. F1/1: Price tag: $52 million. Holy samoleons!