Green’s Dictionary of Slang

1. (US) a devotee of swing music, this adj. sharpy.

1936		A.E. Duckett ‘Truckin ’round Brooklyn’ in N.Y. Age 25 July 7/1: Yvette is looking cool in yellow and Unis appearing drapey with a ‘sharpey’ moustache.
1939		Detroit Free Press (MI) 17 Sept. 8/3: ‘Geemininy willikinazzy, a fellow can’t wear clean white shoes to a swingaroo like tonight, can he?’ ‘Maybe those sharpies from Canuck High can’.
1977		(ref. to 1920s–30s) Daily Mirror 20 Aug. 10: For the fans of the Thirties it was Crosby, for the sharpies of the Twenties it was Jolson.

2. (US) a slick operator, one who lives and hopes to prosper by their wits.

1941		W. Winchell On Broadway 5 Nov. [synd. col.] A six-foot sharpie who tippd the scales at a hot 125 pounds, but would do anything as long as they was a price attached.
1953		R. Chandler Long Good-Bye 75: Three booths down a couple of sharpies were selling each other pieces of Twentieth Century Fox.
1963		G. Lambert Inside Daisy Clover (1966) 242: She’s a real sharpie and has picked up a lot of cute expressions.
1966		J. Holledge Great Aust. Gamble 130: [N]o other sport attracts sharpies and tricksters as does the turf.
1969		‘Iceberg Slim’ Pimp 39: He was a ‘sharpy’ from a number-racket family in New York.
1970		‘Red’ Rudensky Gonif 60: At that moment, I couldn’t picture him the leader of scores of sharpies, guys who sliced up the biggest gangland empire in history.
1989		C. Hiaasen Skin Tight 102: He got wise, hired a bunch of young sharpies, all board certified.
1998		P. Doyle (con. late 1950s) Amaze Your Friends (2019) 74: ‘Two or three of the sharpies [...] go back to civilisation a few thousand quid richer’.
1999		Wash. Post 7 Nov. X06: The private eye, as traditionally conceived, is a sharpie, a wisecracking, hard-drinking, aloof tough guy.
2004		J. Ellroy ‘Jungletown Jihad’ in Destination: Morgue! (2004) 343: Pellegrino: strong-arm goon, shakedown sharpie.

3. a cheat, a liar, a confidence trickster.

[1872		Fife Herald 8 Aug. 4/1: Yon sly whutret [i.e. weasel] o’ a lawyer, ca’d Sharpie].
1942		Berrey & Van den Bark Amer. Thes. Sl. §436.2: cheat, sharp, sharpie.
1957		‘Ed Lacy’ Lead With Your Left (1958) 6: You even enjoy looking like a seventeen-year-old sharpie—you eat up the amazed look when people finally believe you are a real cop.
1999		G. Seal Lingo 146: The scope in gambling for cheating and chicanery was, and is, almost unlimited, so it is not surprising to find many gambling terms related to less than honest practices. These included: cardsharper which is still in occasional use and has probably given us sharpie, a sharp person, one who is not to be trusted.
2004		E. Weiner Drop Dead, My Lovely (2005) 246: The bad side of the street. Where the sharpies and the hustlers play.
2012		D. Spivey ‘If You Were Only White’ 49: [T]he hustlers suggested upping the ante. He obliged, and the sharpies then played him for real, quickly relieving him of five dollars.

4. (US) a stylish dresser.

1951		Dinah Washington ‘New Blowtop Blues’ 🎵 Now I used to be a sharpie / All dressed in the latest styles.
1964		R.S. Gold Jazz Lex. 273: sharp, adj. [...] cf. general and teenage slang sharpie (i.e., one who is well-groomed and flashily attired).

5. (US) anything in conspicuously good condition, esp. a motorcar.

1960

C. Cooper Jr Syndicate (1998) 75: [of a boat] The days when I could pull a fifteen foot sharpie around the world.