Five Most Devious Anti-Heroes in Literature

Ah, anti-heroes. The morally ambiguous and sometimes downright devious protagonists that we can’t help but follow (and maybe even root for). You love to hate them and may even find yourself unable to turn away from them. The characters on this list manage to draw you in and may make you sympathize with them, even though they are some of the most dastardly characters ever put to page. Without further ado, let’s get started…

5. Humbert humbert- lolita 

Via Pinterest

Starting off our list is depraved pedophile and killer, Humbert Humbert. Humbert is ‘love’-struck by twelve-year-old Lolita and, over the course of the novel, rationalizes his dark urges towards her. It is through Nabokov’s engaging and beautifully rendered prose that we find ourselves beginning to almost sympathize with Humbert, which is part of why Lolita came to be considered as one of the greatest novels ever written.

4. jay gatsby- the great gatsby


Surprised to see this iconic character on this list? Well, after re-reading this book when I no longer was in high school English class, I realized that Gatsby has done some pretty questionable things. Sure, he did everything for his love of Daisy, but he still stole, lied, and was even an accomplice to manslaughter! Jay Gatsby is the sort of protagonist that we’re not supposed to admire or look up to, but rather one we’re supposed to learn from based on his various shortcomings.

3. alex- a clockwork orange

This gleefully disturbing novel by Anthony Burgess broaches the questions surrounding morality and immorality through its protagonist and sociopathic anti-hero, Alex. Alex commits all sorts of violent crimes until he gets ‘treated’ by the government through a series of grueling tests. The brilliance of this novel arises in how you almost want Alex to resist the conditioning and revert to his old, violent ways.

2. patrick bateman- american psycho 

Via Amazon

You may know this name more for the movie adaptation starring Christian Bale as Patrick Bateman, a Wall Street financier who also happens to kill people in his spare time. Despite this, he is still so relatable and likable in so many other ways that you just sorta can’t help but like him. A perfectly psychopathic anti-hero you just can’t look away from.

1. woland- the master and margarita

Via Amazon

This anti-hero steps up the destructiveness a bit by being the actual Devil himself. Woland travels around Russia in this Mikhail Bulgakov novel causing wanton death and pain for many of the book’s characters: demonstrating the unpredictability of evil. Anyone can suffer at any time. Woland is still deeply interesting however, and wickedly complex, which gets him on this list.

Can you think of any other Walter White-esque characters that belong on this list? Be sure to share and comment your ideas!

Featured Image Via Medium