Posted by Brian from Shawnee on October 26, 2010 at 17:49
In Reply to: That's how I roll posted by Debpriya De on October 23, 2010 at 18:33:
: What is the origin of the expression "that's how I roll"?
: It probably means "that is how I am or that is how I work".
You're correct about the meaning, and the phrase also carries an implied shrug of nonchalance when your behavior is challenged. There's a post on UrbanDictionary.com under "that's how we roll" from 2004.
I first came across the verb "to roll (with)" meaning "to hang around (with)" while watching the 1995 movie Clueless. A rap song called "Rollin with My Homies" by Coolio is featured in the movie.