Very well then. :P

Pee-wee Herman vs. Tony Soprano
Pee-wee will use a chair that freakin talks (hey look!) and hide behind the fish (holy crap!) before taking a big machete and chopping Tony Soprano to bits. .

The Grim Reaper vs. Olcadan
Grim Reaper will stumble into an SC3 stage and get cussed at by Olcadan for screwing up the combos and inputting the wrong buttons before snapping and killing Olcadan.

XS3 vs. Glaurung
I have no idea who this guy even is but XS3 should be able to take him down. I mean... Come on, he beat the almighty Wiimote! .