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Weaving and driving fast through the streets of a residential area or just a low traffic non-mainstream road or part of town.

(Cutty meaning taking an alternative route home that is off the main road i.e. "I took the cutty way all the way home.")

(And shark meaning to drive fast and wind your way through sharp turns and stops signs typically of a neighborhood, and to do so with the agility and speed of a shark.)

Hence the phrase "cutty shark"
Freeway rush hour traffic was a bitch so we cutty sharked it through the side streets to make it home in time for dinner.
by skrillykillex November 11, 2011
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2
Alludes to position of leadership over subpar class of people. Stems from the Latin phase King Cutty Shark, inventor and President of Urban Prowlers, an online crew of malcontent caucasian wiggers
Cutty Shark destroyed the lives of many a white internet textcee, from Defc0n, to Len Duggan, to the Joker
by MC Aloe Vera September 02, 2011
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3
A local kid in your town who steals and commonly uses methamphetamine.
I almost got jumped by that cutty shark back there
by Jairo Ortiz March 31, 2005
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4
used under the most boring conditions, meaning to leave your current situation.
aye, fuck this, lets cutty shark.
by jewish krime brigade August 23, 2004
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