User blog comment:Bantha117/Captain Hook vs Maleficent - ORRBoUDQ (OGTTIAL) Season 2 Finale/@comment-25308451-20151129062133/@comment-25308451-20151130005801

More suggestions:

Riddler vs Socrates

Bobby Fischer vs Mike Tyson

Alexander the Great vs Spider-Man or Ivan the Terrible or Genghis Khan

Luke Skywalker vs Harry Potter

Benito Mussolini vs Rocky Balboa

Louis Armstrong vs Ray Charles

Link vs King Arthur

GLaDOS vs Marie Antoinette

Gabe Newell vs Shigeru Miyamoto

And I like the ideas of you guys doing House vs Hippocrates, Charlie Brown vs Someone, Milton Hershey vs Willy Wonka, Alex Trebek vs Nostradamus, Joffrey vs Caligula, and Henry VIII vs Churchill.