Green’s Dictionary of Slang

(orig. US) insignificant, unimportant, cheap; also as n., insignificant stuff or activity.

[1855		‘Q.K. Philander Doesticks’ Doesticks, What He Says 259: Napoleon spends most of his time playing penny ‘ante’ with the three Graces].
1865		Nation Vol. I n.p.: Look at those fellows now! . . . ain’t they a ‘penny ante’ lookin’ lot.
1897		Wkly Messenger (St Martinsville, LA) 27 Feb. n.p.: [advt] No penny-ante business at E.E. Soulier The Poor Man’s Friend One Price to All.
1907		D. Runyon ‘Fat Fallon’ in From First to Last (1954) 28: He’s down in Arizona now, commanding a penny-ante post on the desert.
1916		J. Lait ‘Omaha Slim’ in Beef, Iron and Wine (1917) 117: Votin’ don’ do no good. That’s peanut stuff—retail pennyante.
1930		J. Lait Gangster Girl 26: You miss those penny-ante punks you thought were big shots in Chi.
1940		B. Appel People Talk (1972) 278: It’s a penny ante business.
1943		R.L. Bellem ‘Feature Snatch!’ Dan Turner - Hollywood Detective Feb. 🌐 He was a cheap two-bit grifter and penny ante louse around town.
1952		W.R. Burnett Little Men, Big World 210: No more penny-ante jobs with the police department or the D.A.’s office for him. He was a big man now.
1953		Kramer & Karr Teen-Age Gangs 146: The penny pimps and two-bit whores – were barred.
1957		‘Weldon Hill’ Onionhead (1958) 77: ‘Now report me, you penny-ante dictator’.
1960		E. De Roo Big Rumble 111: Whatever they scrounged knocking off parking meters and vending machines in other parts of town was penny ante.
1965		(con. 1940s) Malcolm X Autobiog. (1968) 143: Those penny-ante squares who came in [...] putting on their millionaires’ airs.
1971		T. Thackrey Thief 288: But damn if I didn’t let a cruddy little penny-ante safe-cracker named Shorty, into ‘just one more’ score.
1978		H. Selby Jr Requiem for a Dream (1987) 176: We jus gonna wheel an deal an not go fuckin with any penny boolshit.
1981		J. Ellroy Brown’s Requiem 214: I collected the bets, sent guys to the track to place them, that kind of thing. It was penny ante.
1990		S. Morgan Homeboy 98: Killing machines [...] were inexpendable; not so pennyante players like Frank.
2001		J. Stahl Plainclothes Naked (2002) 131: A cop-killing police chief? Come on, that blows away all that penny-ante Ramparts shit.
2015		P. Beatty Sellout (2016) 67: Like asking some penny-ante lounge singer if they knew the way to San Jose.
2018		‘Aidan Truhen’ Price You Pay 56: She believes in things like ethics which is why Sarah has a penny-ante practice in a terrible office.