The thrilling conclusion to Literary Hub’s inaugural Ides of March Madness bracket:
The Best Villains in Literature.
Article continues after advertisement
After six rounds of voting and thousands of ballots cast, we have our winner, the best villain in literature: O’Brien, George Orwell’s secret police spy, torturer, and totalitarianism-is-actually-good-for-you explainer.
We started with 64 villains from all over literature and slowly whittled them down to one. In the end, it wasn’t particularly close, and 1984’s main antagonist beat Satan by a pretty wide margin. Maybe voters ultimately decided that the self reflection and doubt on display in Milton’s poem makes Satan less decisive than O’Brien, who lies to Winston for half of the book and then tortures him for the second half. O’Brien leaves you with no doubt that he’s a villain. He’s unsubtle and unyielding: “The object of persecution is persecution. The object of torture is torture. The object of power is power.”
We’ve been sharing our staff brackets and picks all last week, and one thing we’ve wondered is what our favorite villains reflect about us: are the things we’re drawn to in an evil character a reflection of what we fear? Or what we dislike in ourselves? In hindsight it seems fitting that the character who revels in the confident and sneering victory of authoritarianism would be the character most on our minds in 2025. What could be more evil than a man who confidently explains that he knows what’s best for you, that there is no truth beyond what he says and that there will be no laughter or sex in the perfect society, and “no distinction between beauty and ugliness”?
Maybe we didn’t see this ending coming, but a character like O’Brien would have bet on himself: “Don’t deceive yourself. You did know it — you have always known it.”
Here’s the final, full bracket:
(Click for a full-size, zoomable image)
Thank you so much to everyone who voted! What literary bracket would you like to see next? Let us know in the comments.
