Welcome to the final round of Literary Hub’s inaugural Ides of March Madness bracket:
The Best Villains in Literature.
Article continues after advertisement
This is it: the final villains matchup, our top two going head-to-evil-head.
After a lot of big upsets, it’s come down to Satan versus O’Brien. Two power-fetishizing characters with a love of dominance for the sake of cruelty and an unfeeling disregard for those they crush. As surprised as we’ve been at the outcomes this week — No Ripley? No Richard III?! — it’s not at all surprising that cruel authoritarians and their servile bootlickers have been the most resonant with people.
Who will win this final vote? The startlingly complex Satan from Milton’s Paradise Lost? This isn’t your Sunday service Satan or your red-caped vaudeville Satan, this is the anti-villain Satan, who muttered that it’s better to rule in hell than serve in heaven, who was cast out and sought his revenge, and who doubts himself along the way. And he’s got a huge army of demons, which you hate to see.
Or the Inner Party member and Thought Policeman O’Brien from 1984? He’s a recognizable foe, a cynical torturer who admits that the whole game for the Party is “the thrill of victory, the sensation of trampling on an enemy who is helpless.” He deceives and lies, and makes no apologies or concessions. Plus he’s the rat torture guy.
Get these two in the same room, and really bad things are going to happen.
Be sure to read our staff odes to our favorite villains, including Calvin on the despair and reality of suburban ennui, Dan on the tragedy of Frankenstein’s Monster, Dwyer on the performances of Tom Ripley, Jessie on Ahab the Boyboss, Brittany on the apex-awful Trunchbull, and more.
And the bracket’s on the Lit Hub Podcast this week: Drew, Oliver, and James talked about the week’s been like, what has surprised us, and which of the four categories is the most literary.
But no more dilly-dallying, it’s time to end this thing, once and for all.
It’s time to crown a winner — for the last time, voting is now open!
Check out the updated bracket and start voting below:
[Click for a zoom-enabled version]
Rules
You may be wondering: What makes a villain “best”? That, friends, is really up to you. You can vote for the most iconic villains, the most memorable villains, or the most villainous villains. You can vote for the villain you enjoyed reading about the most, or the one that kept you up at night. You can vote for the cutest villain, if that’s your thing. The point is, there are no rules. Villains are rule-breakers, and so are we.
Voting Schedule
Ignoble Round of 64: Voting open now until Sunday, March 9th at 7:00 PM EST
Round of 32 Assholes: Voting open now, from 10:00 AM – 7:00 PM EST
on Monday, March 10th
Not-So-Sweet 16: Voting open from 10:00 AM – 7:00 PM EST on Tuesday, March 11th
The Hateful 8: Voting open from 10:00 AM – 7:00 PM EST on Wednesday, March 12th
The Drawn and Quarter Finals: Voting open from 10:00 AM – 7:00 PM EST on Thursday, March 13th
The Final Showdown: Voting open until 7:00 PM EST on Sunday, March 16th
And the Best Villain In Literature will be announced on Monday, March 17th!
How To Vote
You know this by now: simply select the villain you think should win, and we’ll tabulate the votes; on Monday we’ll reveal the Best Villain in Literature.
SATAN (1) vs. O’BRIEN (1)
(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
Thanks for voting!
