From Rap Dictionary
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  1. To hang with a given person or crowd. "I'm rollin' with the new jack crew" -- Ice-T (Newjack hustler [1991]).
  2. To roll on someone means to beat someone up.
  3. To roll a joint.
  4. To drive one's car in the neighborhood with a certain style or finesse.
  5. to do a job e.g. on a raid for doe --kingknocker
  6. an ecstacy dose, "I am rolling so hard right now, PLUR guys, PLUR"
  7. To rollerblade; freestyle rolling.