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1) The way in which a 'gangster' sits in the driving seat of his 'ride'. ie, leaning towards the passenger seat, with one arm resting on the glove/tape box in the middle, the other hand on top of the wheel and head ducked low under the rearview.

2) A type of walk or bowl employed by a 'gangster' that makes it look like said gangster has a slight limp from prehaps having a 'cap' 'popped' in their leg.
Thus leaning to the opposite side and taking the weight of the injured leg produces a gangster lean. An injured leg however is by no means a prerequisite for having a gangster lean, many addopt the style in an effor to look 'hard' or 'cool'
Lyrics from: William DeVaughn - Be Thankful for What You Got
"Diamond in the back, sunroof top
Diggin the scene
With a gangster lean, wooh-ooh-ooh"
by e_mpika May 17, 2006
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The original 'gangster lean' came from old gangster movies and may have even been taken from real life. When fleeing (usually from the scene of a crime) and a car pulls up and you jump on the side of one of those old gangster cars like a 1937 Hudson Terraplane, and you lean on the outside of the car until you're far away.
From Roman Polanski's 1974 timeless crime/mystery classic 'Chinatown'. Jack Nicholson and Faye Dunaway are told to get into a car by some thug, and Nicholson goes to beat him up while Faye takes the car and starts it towards Nicholson as he jump onto the car and does the 'gangster lean'.
by BushwackerJones June 21, 2007
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1.Leaning, with your right hand on the wheel,out the window, with rap blastin' out the speakers, and bouncin' to the beat.

2.Leaning a girl frontward, lifting up her skirt, or pulling down her pants, and inserting dick in pussy for a better sensation.
1."Joe was Gangster LeanIng when he hit the stop sign.

2."I wanna Gangster Lean yah bitch!"
by Jessy Plouffe May 11, 2006
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