Inferno, Dante Alighieri
You know when somebody is complaining to you about something, and you keep thinking it could be way worse, but you struggle to find something witty to compare it to? You could just say, “At least you aren’t descending into hell with a dead poet, only to end up coming across Satan and his three faces, half-immersed in ice, chewing on Brutus, Cassius, and Judas Iscariot while weeping.” This is the ultimate, and most terrifying example of eating your feelings that we can think of, and it is the only appropriate way to end a trip through Hades.
Paradise Lost, John Milton
Milton’s epic 17th-century poem gave us a charismatic and almost likable Satan who knew that it is always “Better to reign in Hell, than serve in Heav’n.”
Faust, Johann Wolfgang von Goethe
Faust is, of course, an old German legend that predates Goethe’s play, and resembles the biblical tale of Job — but the trickster Mephistopheles, while not exactly likable, would probably make for far better company than the horrible monster that Dante saw.
The Devil in Love, Jacques Cazotte
Published in 1772, this story finds the devil falling in love with a man and disguising himself as a woman to win his affection. Some people consider it a very early example of the fantasy genre.
“Litanies of Satan,” Charles Baudelaire
While Satan doesn’t actually show up in this poem, which is part of Les Fleurs du mal, only a decadent creep like Baudelaire would pen something blasphemously great as “Les Litanies de Satan.”
The Mysterious Stranger, Mark Twain
You grow up thinking that Mark Twain was all “aw, shucks” American fun, and then you read the last novel he attempted to write and realize how much contempt he had for the human race, as well as how dark the Huckleberry Finn creator could get.
And even if you don’t count The Mysterious Stranger among his seminal works, it did inspire one of the creepiest kids’ cartoons ever:
The Master and Margarita, Mikhail Bulgakov
We’d be a fan of Woland even if he didn’t hang out with a massive talking cat named Behemoth, but the fact that he inspired one of the greatest songs by the Rolling Stones is enough to make us love him.
The Exorcist, William Peter Blatty
The movie version may be more frightening and visceral than the original novel, based on a 1949 case of demonic possession and exorcism that Blatty had heard about, but the demon in this book will also mess you up pretty bad.
The Sandman, Neil Gaiman
What would one of the greatest graphic novels ever be without a little devil in it? In his greatest work, Gaiman gave us a suave and debonaire devil that was cut from the same cloth as Milton’s Satan.
The Stand, Stephen King
Even though King never explicitly states that Randall Flag is Satan, he is the personification of evil that does battle with good after most of humanity has been wiped out. So we’re just going to go with the idea that King had some New Testament stuff in mind.