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2.
Adj. Describes something that is both stupid and funny at the same time.
When Brandon skateboarded into the road and got hit by a taxi, it was stupidfunny.
by Mr. Aaron October 03, 2005
 
1.
Funny, but not because of humor brought forth by a logical statement. Instead it's funny because the person or thing being such acts in a stupid way.
Person 1: Did you see the latest Fred video on YouTube?
Person 2: Yeah. *laughs* He's so stupid-funny.
by Xman490 June 08, 2009