gangster, adj. — Green’s Dictionary of Slang

gangster adj.

1. (US black) pertaining to a rebellious, non-conformist lifestyle.

1980		E. Folb Runnin’ Down Some Lines 120: Gangster is an adjective that refers to something good or exceptional and, like many other synonyms for fine and exceptional in black vernacular [...] inverts standard white usage for the words. Bad becomes good.
1994		N. McCall Makes Me Wanna Holler (1995) 105: They added imitation ‘gangster’ whitewall tyres and long, gaudy TV antennas.
2018		‘Aidan Truhen’ Price You Pay 77: [H]e’s a fucking white guy pretending to be a Hispanic guy because he thinks that’s more fucking gangster and that is just straight out racist.

2. (orig. US) in pl., the female breasts [? link to gangster front , which, with its wide lapels, emphasized the chest area].

1995

S. Moore In The Cut 122: gangsters, breasts.

gangster doors (n.) [the style of car preferred by prominent ghetto criminals]

(US black) the four doors of a saloon car.

1980

E. Folb Runnin’ Down Some Lines 112: Like my ride’s a Lincoln wid d’ gangster doors.

gangster front (n.) [front n.¹ (3); the style of suit worn by the (movie) gangsters of the 1920s–30s and adopted by latter-day ghetto criminals]

(US black) a double-breasted suit.

1980

E. Folb Runnin’ Down Some Lines 239: gangster fronts Style of dress associated with the gangster.

gangster lean

see separate entries.

gangster pills (n.) [? they slow down the gangster’s natural energy]

(US black) barbiturates.

1969		R.R. Lingeman Drugs from A to Z (1970).
1977		L. Young et al. Recreational Drugs.
2001		ONDCP Street Terms 10: Gangster pills — Depressants.

gangster ride (n.) [ride n. (2a)]

(US black) an old-fashioned, large, poss. black car (cf. G-ride under G adj.²).

1972		E. Folb Urban Black Argot 138: Gangster Ride an old model car, esp. from the era of the 30’s and 40’s.
1980		E. Folb Runnin’ Down Some Lines 112: Den you got yo’ gangster ride. Could be a big ride, like a Cadillac.
2004		D. Koontz Face 163: This was a getaway bucket with style, maybe a G-ride, a gangster ride, stolen out of a driveway in Beverly Hills.

gangster stick (n.) [stick n. (6d)]

(US black) a marijuana cigarette.

1980

E. Folb Runnin’ Down Some Lines 172: [Marijuana’s] dubious legal status is even more prominently acknowledged in terms like [...] gangster sticks.

gangster walls (n.) [SE (white)-walls; i.e. the style of wheel preferred by successful ghetto villains]

(US black) white-walled tyres.

1980

E. Folb Runnin’ Down Some Lines 120: Got a ’64 Chevy, black, gangster walls, tinted window. Looks good.