I've been messing around with the
Random Pairing Generator and here are some examples and commentary
Anya (BtVS)/Susan (Chronicles of Narnia)
-This seems to have some possibilities, possibly talking about lost glories.
It would probably depend on where each of them was in their personal timelines.
Light Yagami (Death Note)/The Devil (Sinfest)
-I haven't read a lot of Sinfest, but I've got the impression the Devil there is fairly
mild-mannered, which means Light would scare the Hell out of him.
Claude Monet (painter)/Rufus (Bill and Ted's Excellent Adventure)
-The scary part is, this is entirely possible within Bill and Ted continuity.
Lyra Belacqua (His Dark Materials)/Ashton (Star Ocean 2)
-Good God. Poor Ashton would be even more doomed then usual.
Cleopatra/Hercules (HtLJ)
-Wait, isn't that canon?
Media (American Gods)/Wonder Woman
-.....Y'know, I can see how this could be mind-boggling cool, but only if a writer like Rucka or Gaiman was writing it..
Mamoru (Sailor Moon)/Bubbles (Powerpuff Girls)
-...I dont think he's into girls that young.
Captain James T Kirk/Barbossa (PotC)
-OK, my brain is officially broken. G'night all.