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1.
Phrase used in an infamous rap battle that led to a fight. It is now commonly used to further anger a person who is not up to par with your style (or anything for that matter). Studies have shown that the use of the words 'Oh u mad' before the phrase further irritates the person.

see: u mad, cal is on me, o rly?
"Oh u mad 'cause I'm stylin on you!"
by Adam aka Im Better Than You January 01, 2007
 
2.
to be hotter, flyer, and just overall better than you
"oh you mad cuz I'm stylin' on you?"
by ayeDub April 24, 2008