7. Bill & Ted vs. Harold & Kumar
This is a hard match. Harold & Kumar are older and significantly more intelligent, but Bill and Ted have the power of time travel on their side. In this fight, it's really a question of motivation: none of these four guys are going to be bothered to get in much of a tizzy for
just anything. A mere trophy wouldn't be enough to get either team into the game. I would say that Harold and Kumar are more single-mindedly determined to reach their goal of getting White Castle, refusing to give up after a myriad of misadventures. Whereas Bill and Ted tend to fly by the seat of their pants, although they do manage to fix a broken time machine, so maybe they've got more smarts than we give them credit for.
Who Would Win: I imagine that they would probably lose interest pretty quickly, and all just decide to take a quick trip to Colorado because of reasons. The tiebreaker in this round will have to be their sidekicks, which in this case is George Carlin vs. Neil Patrick Harris. The victor? George Carlin, easily.