Palom. Niko Bellic (GTA IV) vs. Trevor Phillips (GTA V) vs. Tommy Vercetti (GTA:Vice City)vs. Carl Johnson (GTA:SA) in a Four way fight to the death.
CJ. He's the physically the strongest, and probably the best shot, too. (At least he was when I played the game.) Yuri Lowell (Tales of Vesperia) vs. Lloyd Irving (Tales of Symphonia) in a duel to knockout.
Sailor Venus knows how to right wrongs and triumph over evil way better for sure! The Joker vs Jason Voorhees highest body count wins
Jason Voorhees has 154 kills. The Joker has at least 160 confirmed kills, and many more hinted at. Batman with a Green Lantern ring vs. Superman in a fight to knockout.
Julius Caesar, because Napoleon would make very dangerous moves and then rage quit when they don't work, and Alexander would be too focused on working it like real war as opposed to a board game. Duke Nukem (Duke Nukem) versus Eridan Ampora (Homestuck) Two totally unrelated characters! (I swear if one of you replies with "I dunno who that is so Duke Nukem" I will personally come to your house with the intent to kick butt and chew gum, and I will have ZERO ACCESS to gum.)
I don't know much about Silent Bob.. but he has Silent in his name.. and Fluttershy would scream if something upset her so Silent Bob. Twilight Sparkle vs Starswirl the Bearded in a proper magic duel. (Even though Twilight ascended by understanding friendship when he didn't, Starswirl did create a huge number of spells and Twilie only created one. That said he was alive a long time ago and there have likely been a lot of advancements since them. Also Twilie has had time to study the spells he made and others.)
Wario. He cheats. (If you had said Sterling Marlin, it may have been an even match.) Bear with an axe vs. kangaroo with a sword.
I've only seen two episodes of LPS, but I don't recall the Biskit twins making fun of the disabled. Skwisgaar Skwigelf vs. Satan in a rock-off.