
I think in a marksmanship competition, it's pretty clear that Oswald can far out shoot Booth. The man uses magic bullets for god's sake. Plus, Oswald was a sniper, and Booth was more of a side arms kind of guy, so in terms of hitting the target (the other assassin) I feel like the match goes to Oswald. And even beyond marksmanship, preparation was a big part for the both of them, but I feel like Oswald still takes the cake. Booth is an actor, so maybe if he needs to go in disguise to get to Oswald he can win, but planning wise, how well did he really think things through? He had the killing part down to an art, but then what? I can't see Oswald, no matter how crazy he is, leaping off a second story balcony, breaking his leg in the process, yelling some b.s. in Latin and then darting through a heavily guarded hallway. Not gonna happen.
Winner: Lee Harvey Oswald.
Round 2. Mini-Me v. Froddo Baggins.
I can see this fight playing out pretty straight forward in my head. Mini-Me starts out on top, completely taking ol' Froddo by surprise with his incredible knowledge of martial arts. Using a nearby bottle, Mini-Me becomes a force to be reckoned with as

Winner: Froddo Baggins
*Addendum* If Mini-Me can stay alive for long enough, I think its a fair call that the Ring Wraiths will show up and just behead the little hobbit faster than you can say "Yeah Baby, Yeah." In this case...
Winner: Mini-Me.

This is a tricky one. Giant pterodactyls are notorious for their ability to re-grow any flesh that gets shot off by a Wookie Bowcaster. I foresee Chewbacca having a pretty hard time shooting the thing out of the sky, given that particular regeneration factor. But on that same token, the giant pterodactyl is unable to attack Chewbacca from a distance simply by its very nature of being a primitive being. It's all going to come down to one deciding moment. The dino is going to need to get close enough to attack Chewie eventually, and that will be the chance for both of them to strike. Chewbacca will make an attempt to jump on the the giant pterodactyl's back and actually de-wing it midflight. A tricky feat indeed, as all the while the monster will be trying to reach it's neck far enough around to catch Chewbacca in it's massive jaws. This is where the battle is won. A fight of this kind can only happen when the two meet, and giant pterodactyls only hunt at night. Keep in mind also that Chewbacca only goes out that late during the full moon on Kashyyyk, to visit a monthly family reunion. So luckily for Chewbacca, the full moon will draw hoards of moths, confused by the lunar cycle, who will effectively distract the preoccupied giant pterodactyl giving everyone's favorite Wookie the upper hand, and the victory.
Winner: Chewbacca.
Look for John Wilkes Botth in the eventual post "Stupid People In History!"
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