User blog comment:GravityMan/Literature vs History Season 1 News with Jay Gatsby/@comment-5393732-20151205035758/@comment-5393732-20151205043006

Holden vs Bueller is two badass rebellious teenagers that live by their own rules

1984 vs Truman Show would be like Winston vs Truman, with Big Brother and Christoph coming in at the end or something

Jack Meridou is the antagonist of Lord of the Flies; connection is two violent and characmatic leaders that rally the support of many others

And since graphic novels count as lierature:

V vs Che Guevara

Marv (Sin City) vs The Bride (Kill Bill)

Dr. Manhattan vs Marie Curie

Other suggestions:

Jurgis Rudkis (The Jungle) vs Ronald McDonald

The Hardy Boys vs Sam and Dean

Lisbeth Salander vs Neo

Willy Wonka vs Milton Hershey

Alice vs Chihiro (Spirited Away)

King Arthur vs Indiana Jones

Macbeth and Lady Macbeth vs Bonnie and Clyde

Patrick Bateman vs Donald Trump

Hannibal Lecter vs Vlad the Impaler

Paddington Bear vs Chucky

Robinson Crusoe vs Gilligan

Count Olaf or the Baudelaires have to be in a battle at some point

The Three Musketeers vs Batman, Robin, and Batgirl (I have no idea, they were the first vigilante trio I could think of)

Captain Ahab vs Jacques Cousteau

Billy Pilgrim (Slaughterhouse Five) vs Phil Connors (Groundhog Day)