two-bit, adj. — Green’s Dictionary of Slang

two-bit adj.

also two-bits

[SE two +bit n.¹ (1), lit. worth 25 cents]

(US) second-rate, inferior.

1904		N.Y. Eve. Post 12 Feb. 5: Out in the ‘two-bits’ country, on the other side of the Rocky Mountains, it is still possible to pass Confederate paper money [DA].
1916		J. Lait ‘Canada Kid’ in Beef, Iron and Wine (1917) 174: There he was, a sidewalk curbstone faker, peddling with droning voice two-bit swindles to the Christmas crowds.
1928		N. Welsh ‘Chicago Women Blues’ 🎵 Keep on drinkin’ that two-bits whiskey / You’re gonna drive your poor man away.
1928		R. Carr Rampant Age 232: Last night, in Buffalo, we blew ourselves to a two-bit hotel.
1934		(con. 1920s) J.T. Farrell Young Manhood in Studs Lonigan (1936) 381: These goddamn two-bit jellybeans around the place.
1947		B. Schulberg Harder They Fall (1971) 10: Grifters, chisellers, two-bit gamblers, big-time operators with small-time minds.
1958		C. Himes Real Cool Killers (1969) 63: You look like two-bit punk to me.
1967		(con. 1940s) M. Dibner Admiral (1968) 220: A bastard son of a cheap two-bit ward-heeling bitch in a Brooklyn slum.
1979		‘Iceberg Slim’ Airtight Willie and Me 47: She got the hots for a two bit hustler.
1989		C. Hiaasen Skin Tight 76: That’s pretty rich coming from a two-bit doper.
1994		N. McCall Makes Me Wanna Holler (1995) 152: It made me feel like I was a political prisoner rather than a two-bit stickup man.
2004		M.B. ‘Chopper’ Read Chopper 3 19: If most of the two-bit crims had her dash, guts, and courage, they would never tell tales out of school.
2009		N. Flexner Disassembled Man [ebook] A two-bit ex-con who enjoys hot dogs and beer more than caviar and Sxcotch.
2016		Twitter 20 Nov. 🌐 Trump isn't the real menace; he's a two-bit grifter. The menace is the monsters he's enabling.
2019		S.M. Jones Lives Laid Away [ebook] ‘You a two-bit Uncle Tom niggah just like yo dead old man’.

In compounds

Two-bit Annie (n.) (also two-bit Sadie) [+ proper name]

(US) a cheap prostitute.

1948		(con. 1944) N. Mailer Naked and Dead 14: Just there be Two-bit Annie around the corner when he felt like company.
1950		Goldin et al. DAUL 230/1: Two-bit hustler. [...] 2. A prostitute who sells her favors cheaply. [Also Two-Bit Kitty; Two-Bit May; etc.].
1972		R.A. Wilson Playboy’s Book of Forbidden Words 137: The lowest class of prostitutes [...] in Brooklyn they are dubbed two-bit Sadies.

two-bit hustler (n.) [hustler n.] (US Und.)

1. a promiscuous woman; a low-priced prostitute.

1950		Goldin et al. DAUL 230/1: Two-bit hustler. [...] 2. A prostitute who sells her favors cheaply.
1986–7		Maledicta IX 150: The original argot of prostitution includes some words and phrases which have gained wider currency and some which have not […] two-bit hustler (cheap lay).

2. a second-rate confidence trickster.

1950

Goldin et al. DAUL 230/1: Two-bit hustler. 1. Any petty thief or racketeer.

3. a passive homosexual or low-priced male homosexual prostitute.

1950

Goldin et al. DAUL 230/1: Two-bit hustler. [...] 3. (P) A passive pederast or male oral copulator who is promiscuous and cheap in the sale of favors. [Also: Two-Bit Willy; Two-Bit Tom; etc.].