Screwtape in The Screwtape Letters , C.S. Lewis
In the funniest of C.S. Lewis’ works, Screwtape is an experienced devil sending letters of encouragement and advice to his nephew, the tormenter-in-training Wormwood. “Do remember you are there to fuddle him,” he intones. Also: “Flippancy is the best of all. In the first place it is very economical.” You will giggle much too often to be the least bit frightened.
Darryl Van Horne in The Witches of Eastwick , John Updike
When the only trouble the devil can stir up is sexual scandal in a small town, he’s no scarier than any attractive out-of-towner.
Lucifer in I, Lucifer , Glen Duncan
Duncan’s novel begins thusly: “I, Lucifer, Fallen Angel, Prince of Darkness, Bringer of Light, Ruler of Hell, Lord of the Flies, Father of Lies, Apostate Supreme, Tempter of Mankind, Old Serpent, Prince of This World, Seducer, Accuser, Tormentor, Blasphemer, and without doubt Best Fuck in the Seen and Unseen Universe (ask Eve, that minx) have decided — oo-la-la! — to tell all.” And look, any devil who says “oo-la-la,” in ironic italics no less, is not one likely to strike fear into our hearts.
Mephistopheles in Faust , Johann Wolfgang von Goethe
Sure, Mephistopheles may lead Faust into some pretty hairy situations, but if you get scared, all you have to do is close your eyes and remember that when you first met him, he was a pathetic little stray poodle.
The Devil in The Divine Comedy , Dante
Dante’s deepest sphere of hell is, of course, presided over by the devil, who should be the most terrifying foe yet. But, as it turns out, he really isn’t — trapped in ice up to his chest, he cries with all three of his faces as he chews on and slobbers all over three notorious sinners. Trapped in the same torments he inflicts on the denizens of hell, Dante’s Satan is terrible to be sure, but impotent, too.
The Russian Gentleman in The Brothers Karamazov , Fyodor Dostoevsky
Dostoevsky’s devil, as he appears to Ivan, is rather tattered, a high-born gentleman down on his luck, not obviously frightening but clearly discomfiting to those around him. He has always seemed to us to be the manifestation of a sort of philosophical evil more than a pure, all-consuming one.
The Devil in Paradise Lost , John Milton
Milton’s devil is actually kind of likable at first — the poem’s swaggering, complex protagonist is eloquently broody, waxing on about how it’s “better to reign in Hell than serve in Heaven.” But in the end, he’s twisted by jealousy and his own cynicism, and out for the worst kind of revenge.
Woland in The Master and Margarita , Mikhail Bulgakov
Sure, we might laugh when Woland toys with those pesky bourgeoise, and we certainly appreciate a devilish sense of humor, but Woland is truly sinister — he likes to punish, humiliate, and tease. He thinks that good can only exist in the world as a shadow of the evil he creates. However, his particular motives in catalyzing that evil, unlike other devils, are often unclear, so, like a dull blade, you’re not quite sure in just what direction he might slice.
The old man in “Young Goodman Brown,” Nathaniel Hawthorne
In Hawthorne’s classic short story, the devil is just an ordinary guy — but to us, that’s even scarier than magic tricks and fireballs, because it suggests that everyone has (or has the capacity for) pure evil within them. Chilling.
The Devil in The Exorcist , William Peter Blatty
Nothing is scarier than pure evil stuffed into the body of a little girl.