The Greatest Literary Villains of All Time

[Clint_L]

Not sufficiently literary.

It's possible, though the list already has its share of "non-literary" authors.

 

[Clint_L]

The final showdown: O'Brien vs. Satan. Seems like a mismatch. O'Brien is terrible, don't get me wrong, but Satan has all the branding.

The Best Villains in Literature Bracket: The Final Showdown

Welcome to the final round of Literary Hub’s inaugural Ides of March Madness bracket: The Best Villains in Literature. This is it: the final villains matchup, our top two going head-to-evil-head. A…

lithub.com

SATAN​

(1) Satan (John Milton, Paradise Lost)

Is evil incarnate just a misunderstood bad boy? Our top seed in the anti-villains category is the Western embodiment of wickedness, whom Milton treated with more depth of character and contradiction than anyone else in his poem. Milton’s Satan is still a fallen angel who corrupts Adam and Eve with sin, but as readers, we feel his alienation and frustrations. It turns out even Satan struggles with big decisions.

Weapon of Choice: Army of Fallen Angels, Apples
Reasoning: “Here we may reign secure, and in my choice/to reign is worth ambition though in Hell:/Better to reign in Hell, than serve in Heaven.”
Number of Furies Fierce As: 10

Read: Satanic Sympathies: On the Demon Depictions That Helped Jamie Quarto Write Two-Step Devil

vs.

(1) O’Brien (George Orwell, 1984)

Our top seed for authoritarians is this extremely memorable villain from one of the most widely read books about villainy. Orwell’s O’Brien combines all the worst villains from the real world into one of the nastiest guys in literature: he’s a fascist, a boss, and a snitch all rolled into one, a sort-of fascist Megazord, if you will.

Weapon of Choice: Lying, Rodents, Party-Members-Only Wine
Grim Prediction: “If you want a picture of the future, imagine a boot stamping on a human face—forever.”
2+2: 5

Read: 75 Years of 1984: Why George Orwell’s Classic Remains More Relevant Than Ever and George Orwell’s 1984 is Always Just Around the Corner

 

[DrunkonDuty]

I feel they're different enough characters that comparing them is kinda weird.

 

[Clint_L]

I feel they're different enough characters that comparing them is kinda weird.

Of course it's weird. That's the fundamental premise of the tournament. It's for fun, not serious business.

 

[DrunkonDuty]

I realise I haven't said that I quite enjoyed the competition. I get that it is meant to be silly fun. And I happily embrace that.

 

[Clint_L]

The winner is...

The Best Villains in Literature Bracket: And The Winner Is…

The thrilling conclusion to Literary Hub’s inaugural Ides of March Madness bracket: The Best Villains in Literature. After six rounds of voting and thousands of ballots cast, we have our winner, th…

lithub.com

 

[billd91]

Well, I guess that's not a surprising outcome given recent/ongoing events.

 

[Clint_L]

On sheer literary merit and impact I would have gone with Milton's Satan, but O'Brien is a worthy champion. The rare villain who is not the hero of his own story.

 

[Guest 85555]

On sheer literary merit and impact I would have gone with Milton's Satan, but O'Brien is a worthy champion. The rare villain who is not the hero of his own story.

I agree. I liked 1984 just fine, but I had to think for a moment to remember O'Brien clearly. Satan in Paradise Lost is so satisfying