Gabe Newell vs. Shigeru Miyamoto (Legendary gaming programmers)
Richard the Lionheart vs. Andrew Jackson (High leaders and violent as all hell)
Rick and Morty vs. Mordecai and Rigby (Animated sitcom duos)
Sonic The Hedgehog vs. Usain Bolt/The Flash (Fastest things alive)
Captain Underpants vs. Jared Fogle (For the straight up lols)
Nostalgia Critic vs. AVGN (Classic internet reviewers)
Monty Phython vs. South Park (Masters of dark comedy)
Men in Black vs. X Files (Sci-Fi film/tv show)
...and maybe a few more afterwards, though tbh I'm happy with what's here :)
Sorry for all the fictional stuff, I just really enjoy that I suppose.