Matthew Perry is a master of sarcasm jitsu and would therefore win hands down.
Edward Scissorhands VS Edward (FFIV) VS Edward Elric VS Edward (Cowboy Bebop) VS Ed VS Edd VS Eddie.
Scissorhands ftw.
Green power ranger vs Sinistral
What? No Edward 40 Hands?
The green power ranger and Sinistral don’t have the same name, and therefore IT DOESN’T WORK FOR THIS GAME!
So… I’ll pick one that actually WORKS for you.
Ken from Street Fighter or Kenneth Anger the Satanic director.
A quick Hadoken followed by a Hurricane Kick would end that matchup.
Sid Vicious vs Sid (from Toy Story) vs Sid (from Ice Age)
Sid Vicious cause he’s twice the man you are and he has half the brains you do!
Lex Luthor vs Lex Luger (and while humorous and appropriate, I DON’T KNOOOOOOOOOW does not count >:E)
Also, Hades, Commodore Perry was an American naval officer.
Who cares. We all know that all Americans are brits at heart anyway.
And Canadians are self-hating Americans. 
Luthor - like I said yesterday, it’s easy to see Luger’s steroid use has dropped (and according to 984, an indy wrestler’s salary must not buy much), so the brains win. Plus whatever sort of cyborg suit crap Luthor can make up.
Huey Long (old governor of Louisiana) vs. Huey (Donald’s nephew) vs. Huey Freeman (from the Boondocks)
Huey Louis and the News <_<
Just kidding. Huey Long would fillibuster them all to death! 
Ronald Reagan vs. Ronald McDonald
Ronald McDonald. Not only is Reagen dead, but McDonald has the help of the Grimace, and no one can defeat the Grimace.
Jimi Hendrix VS Jimmy Page
Jimmi page. No contest
Adam Sessler VS adam West VS Adam Savage VS Adam…uhh from…Anger Management
Adam Sandler. He’d win 'cause he’s Jewish.
Guyver (from some TV show) vs MacGyver.
Uh. MacGyver, hands down. He’d build a bomb out of a rubber band, thumbtack, and paper clip. Then he’d build a working Stargate out of cardboard for kicks.
Prince (the Artist Formerly Known as) vs Prince Charles vs Machiavelli’s The Prince vs The Prince of All Cosmos.
Prince of All Cosmos Katamaris the others, then they get fused into a star. No contest.
Now, to bump it up a notch, the Burger King vs the King of All Cosmos vs King from Tekken.
The Burger King. He’d sneak up on the other two before they wake up then stare down at their corpses in that freaky oversized mask-face of his.
Bob the Builder vs. Spongebob vs. Baby Bob
Spongebob for sure. He’d freaking absorb the others.
Sin(istral) vs. Sin (FFX).
Sinistral’s hair kills Sin with pure awesome. Flawless victory. For a 1v1, Jeff (Earthbound) vs Jeff Foxworthy.
Jeff would break Foxworthy’s brain by simply talking to him. Flawless Victory. Leonardo (TMNT) vs Leonardo Decaprio (did I spell his name right? ^^;; )
Leonardo the Ninja Turtle would slice Leonardo DeCaprio in half. What a sissy.
Walter Mosley (detective fiction writer and author of a great nonficiton book called “Workin’ on the Chain Gang”), Walter Cronkite (the newscaster), or the astronomer Bernard Walter.