Green’s Dictionary of Slang

lean v.1

[the image is supposedly that of a pimp cruising the streets with his whores]

(US black/west coast) to drive a car while leaning out of the window.

[US]Current Sl. V:2 9: Lean, v. To drive a car while slouched over toward the left window.
[US]E. Folb Runnin’ Down Some Lines 114: Essentially to lean means to lean inwards from the window, as if you are resting your arm on a console or armrest [...] while steering the car with your left hand (or as a passenger, with your left hand braced against your leg or waist as you lean inward).

SE in slang uses

In phrases

lean against the engine (v.) [the recumbent posture of opium smokers, and the concomitant smoke]

(US drugs) to smoke opium.

[US]Berrey & Van den Bark Amer. Thes. Sl.
[US]Anslinger & Tompkins Traffic In Narcotics 312: lean against the engine. To smoke opium.
on a lean (adj.)

(Aus.) waiting, lit. leaning (e.g. on a wall).

[Aus]Bulletin (Sydney) 26 Sept. 15/1: ’T’ keep a lydy on a lean / Where passin’ cobbers grin ’n’ yap / Is dead low down.