The Shot Glass Checkers Set—as its title implies—is actually for checkers, but as the title of this post implies, I couldn't think of any famous checkers players. The concept could be adapted to chess with some creative glassblowing, though the greater brainpower requirements of that game might not jive with the spirits. After losing (and slamming) three pawns and a rook, I'd probably be trying to move my knight like a queen.
Still, it would be kind of awesome to watch a Great Masters of Chess tournament where the players are struggling to checkmate before they puke.
What we'd like to see next: Connect 4 with quaaludes. "Pretty sneaky sis...zzzz...."