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1.
Badly-cut hair, usually the result of going to a cheapie barber or hair stylist. It looks as if someone took a cup and cut the hair around it.
Mike must've gone to that Turk down on Steinway St. That barber has to go back to barber school 'cos all he seems to know is how to do a cup job.
by pentozali January 29, 2014
 
2.
When you put a balloon inside of a solo cup and have sex with it.
"Seriously, if you put a balloon inside of a cup, and fuck that, that would be better than Anna."
"Wait, what would that be called?"
"A cup job."
by therealfrosty April 02, 2010