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3.
At the bossman's request, cruising the jail house or prison yard picking up cigarrette butts in a large tin can.
If that jit keeps irratating the bossman, he's gonna find himself cadillacing soon.
by Ray April 16, 2004
 
1.
slacking
takin it easy when ur spose 2 b workin
When the bossman's gone home boy be cadillacin'
by homeboy September 03, 2004
 
2.
Cadillacing is just when someone drinks any kind of booze and at the same time or right after smokes some weed. It's getting high and drunk at the same time - CADILLACING
I had a shitty day but i didnt care cuz i knew that later that night i would be cadillacing with my jim beam and chronic.
by Wiski October 30, 2006