I disagree, Yrie. The shirt is about an award wining singer who's actually lip-synching his songs, hence the Milli Vanilli reference. I feel the the design does a good job of explaining that. The comic has nothing to do with lip-synching, and isn't needed to clarify the shirts story. It's just there for added amusement.
Quite honestly, until i read your description, i didn't get the lip-syncing bit, i just thought a bear swallowed the fat lady of the opera and took her prize! lol. I'm not sure how to make it more understandable, but i think it's a really cute design regardless of fully understanding ti or not. Maybe just having the bear performing in an opera or belting out a tune in a dramatic pose instead of holding the trophy? Who knows, maybe most people get it right away, but like i said, a nice clean design and good work!
Bigsbey is setting himself up for an infamous Milli Vanilli-esque fall from stardom.
Scandal!