Pwners:
Phoenix Wright: Actually, pretty much almost everyone who has ever defended/prosecuted, but Phoenix is the best. I don't need to explain.
Dante: The guys near invincible, has a giant sword, two infinite ammo hanguns, and can juggle you in the air until there is nothing left but holes.
James/Henry (SH2/SH4): Both of these people fought off essentially the legions of hell. James did it because he could, there was nothing forcing him in silent hill, oh yeah, and PYRAMID HEAD *shudders*. and Henry beat an invincible ghost who used a revolver and a CHAINSAW and was stuck in his apartment room, where not even there could he find sanctuary from the relentless horde of evil. If you play through SH 2 and 4, you will understand.
Zidane Tribal: Hey, i like the guy. And he does own.
Pyramid head: OH GOD OH GOD I THINK HE'S CHASING ME. nuff said.
Fredrick Francois Chopin: Eternal Sonata is the only game that could make a terminally ill 19th century composer seem friggen awesome
Pwnt:
Sgt. Paul Jackson: The guy was killed by a nuclear bomb, seriously, wtf. What kind of main character can get killed by anything, let alone a bomb.
Cyberdemon: The one from doom 3. Nothing that big should be beat by a lone marine 1/100 of your size, WITH the help of a demon army attacking him alongside you.
John Freeman: well, technically...its from something made from a game.
Gordon
FROHman:
http://www.hlcomic.com/ Comic ended, but its hilarious. Same reason as above.