Ever since Satan in Milton’s Paradise Lost, there’s always been a certain je ne sais quoi about a well-wrought antihero. Whether cheeky rogue or bloodthirsty tyrant, an antihero is a welcome deviation from the white-hatted norm. At once both appalling and subversive, a good bad guy / bad good guy always proves a more interesting character than the morally unambiguous square-jawed hero. There’s something relatable in their flaws, something endlessly intriguing in their motivations; unique in each of their psyches that layers their story, that gives extra weight to their performance. We can learn their lessons or appreciate their many dimensions.

There are a few different antihero tropes, but they all seem to relate to the interplay between humanity and corruption: the good-at-heart but stuck in a corrupt world; the good-once-upon-a-time but corrupted through greed or a quest for power; the satirical embodiment of a corrupt or malicious aspect of humanity. There is something in us that identifies with the antihero: with the feeling of trying to be a good person in a bad world. Is there some level of wish fulfillment as we watch them buck the system and stick it to the man? Is there some tragic identification as we watch them fail? Is there some horrified, looking-at-a-car-crash reaction to seeing the most base elements of our society personified? Really, the protagonist is the person in whose shoes we place ourselves. There’s something deeper and more satisfying about walking in the shoes of an antihero.

The more time passes, exact definition of “antihero” seems to widen, casting a larger and larger net of what we deem antithetical to the traditional hero. Perhaps that’s just postmodernism taking its toll. From the narrowest sense of the aforementioned Prince of Darkness, we’re at the point where even a character like Arthur “all I want is a cup of tea” Dent (Hitchhiker’s Guide to the Galaxy) could be considered an antihero. I guess it’s all in how you look at it. With that in mind, I’ve tried to limit this list to characters that are leading roles (or close to), and who seem to fit the more traditional sense of the title “Antihero.” Regardless of why we love the bad good guys, we can’t deny that we do. I mean, who do you like better, Luke Skywalker or Han Solo? Han Solo, of course, unless you’re under the age of eleven. Perhaps this proves something about developmental psychology, but let’s just leave it at that.

(WARNING: SOME SPOILERS)

10. Captain Jack Sparrow (Johnny Depp)
Pirates of the Caribbean trilogy (2003, 2006, 2007)

Captain Jack SparrowNot the traditional leading hero, (that honour would go to Orlando “Legolas” Bloom) Captain Jack is indeed the heart and soul of the Pirates movies, and you’ll be hard-pressed to find anyone who disagrees with you. Why else would Disney being flogging this dead horse with On Stranger Tides? Jack Sparrow, for all his debauchery, law-breaking, womanizing, drunkenness, and moral grey areas, is one of popular cinemas most endearing and lovable characters. Ever. His own crew can’t even be sure whether or not he is in fact a “good man” but they still sail to the afterlife to rescue him. And you can see him not once, but three whole times on the original ride at Disneyland. Rest assured, you have heard of him.

9. The Narrator/Tyler Durden (Edward Norton/Brad Pitt)
Fight Club (1999)

Tyler Durden / The NarratorIf you think these are two characters, you clearly didn’t watch the movie hard enough. In the relationship/conflict between the Narrator and Tyler Durden, we see the wonderful dichotomy between “good” guy and “bad” guy that exists in every antihero played out in the most literal sense. In the anarchy and violence espoused by Tyler Durden we see a dangerous violence void of humanity – made frightening by an extreme lack of regard for other people and no concern for the consequences. He is balanced by the Narrator, who questions Durden; who cannot escape his own morality despite his disillusionment with the world around him. The cognitive dissonance between the two personifications of this character pulls us in but frightens us: you identify with his disillusionment but fear his instability. At what point does a freedom fighter become a terrorist?

8. Patrick Bateman (Christian Bale)
American Psycho (2000)

Patrick BatemanAn antihero in the most Miltonic sense, Bateman is an actual serial killer – but not even a killer with a misguided sense of morality like, say, Dexter Morgan. Bateman is remorseless and chilling. What makes a character like Patrick Bateman resonate so well, and prove so cultish, is the pure essence of everything he personifies. With the wonderful hindsight we now enjoy, what self-respecting individual these days is not repulsed by the ego-driven, Reagonomics, “greed is good” ethos of the 1980s? The antihero of Brett Easton Ellis’s novel (and Mary Harron’s film) should satisfy conservatives and liberals alike as he literally takes a sharp knife to everything yuppie.

7. Scarlett O’Hara (Vivien Leigh)
Gone With the Wind (1939)

Scarlett O'HaraScarlett O’Hara has stood out for seventy years as one of the most interesting characters – female or not – Hollywood has ever produced. Charming, wealthy, resourceful but rich, spoiled, selfish and vain, Scarlett may have her family’s best interests at heart, but still she steals her sister’s man, steps on many others in her pursuit of her goals, and glorifies a culture that treated human beings as chattel. The fact that she stands as the sole woman on this list, argues three points: 1. The lack of good female roles in Hollywood, 2. Very few anti-heroes are women, and thus 3. Anti-heroes are indeed the most enduring characters.

6. Alex DeLarge (Malcolm McDowell)
A Clockwork Orange (1971)

Alex De LargeAlex is really only one step shy of Patrick Bateman in terms of treachery, and that’s only really because his body count is lower. Let’s face it, Alex is only really an antihero because he’s the protagonist, but in essence, he’s just an out-and-out villain. Robbery, rape, Beethoven – just a usual day’s galavanting. He’s frightening in the same way Bateman is: he’s a psychopath. Remorseless and cruel, he finds sheer delight in torture and he knows full well just what a horrible human being he is. But what is it that about him that people connect with? Why do you always see at least one person dressed as Alex every Halloween? How do we feel sympathy for someone like this when he is cured of his violence? Is it the irony in the forced violence of the cure? Is there something about Alex – and this kind of antihero – that possesses a kind of freedom we can never have?

5. Travis Bickle (Robert DeNiro)
Taxi Driver (1976)

Travis BickleThe tortured vigilante of Scorsese’s Palme D’Or winner presents an interesting moral dilemma, as most vigilantes not riding in a van with Mr. T tend to do. Bickle fits all the aforementioned tropes of an antihero: he feels he is trying to do good in a corrupt world; yet, he slowly becomes corrupted during his quest; and he is iconic of post-Vietnam disenchantment. His protection of a teenage prostitute is honourable…and his killing spree…? Well, that’s a little more ambiguous, isn’t it? Is it honourable because of Bickle’s rationalization of it, or is it a commentary on society that we can somehow find honour in murder?

4. Michael Corleone (Al Pacino)
The Godfather trilogy (1972, 1974, 1990)

Michael CorleoneThere are very few falls from grace as iconic as Michael Corleone’s. Perhaps a very strong part of what makes The Godfather Part II such a compelling sequel (the only one ever to win the Oscar for Best Picture) is that we see Corleone fully transitioned from hero to antihero. Like the true slowly corrupted good guy, he becomes what he was so originally set against: an execution-ordering mafia don. From the kiss of death for his own brother to watching his daughter killed in front of his eyes, it’s pretty clear: crime doesn’t pay.

3. Beetlejuice (Michael Keaton)
Beetlejuice (1988)

BeetlejuiceI’ve always loved Michael Keaton. My childhood crush on Batman not withstanding, he’s always been an excellent character actor and Beetlejuice is the pinnacle of his career – there’s simply no more to it. I firmly believe that this character is the reason for Tim Burton’s career: it was the surprising success of Beetlejuice that gave Burton Batman and everything that followed. Beetlejuice is a little like Jack Sparrow, only you’re pretty sure he’s a bad dude. He frequents brothels, tries to marry an underage girl, and is generally tricksy and mischievous… and charming as hell, despite the creepy teeth. Say his name three times. Go on, I dare you.

2. Daniel Plainview (Daniel Day-Lewis)
There Will Be Blood (2007)

Daniel PlainviewIt’s going to be interesting to see how time handles Paul Thomas Anderson’s epic. Its literary quality far outstrips its potential for a cult following, but every character Daniel Day-Lewis touches proves iconic. Daniel Plainview is the essence of There Will Be Blood, and any lesser actor could not have brought the required charm, sensibility, or deep-seeded cold-hearted ambition together in a way that was anything but a retread of the classic ambition-leads-to-downfall story arch. Anderson and Day-Lewis create a character that so fantastically blends together a million different themes and methods that, rather than being hit over the head with moralising, you get a pure, instinctive sense of the many things a man like Plainview makes you feel: fear, disgust – yet acceptance. An antihero par excellance, Daniel Plainview works on so many levels. He is far more charming than Michael Corleone or Patrick Bateman, but it’s this charm that makes you simultaneously admire and despise him. You want to trust him so badly, but have that strange nagging that you shouldn’t. He is so wonderfully realized but we’re never entirely sure what makes him tick or why.

1. Charles Foster Kane (Orson Welles)
Citizen Kane (1941)

Charles Foster KaneNot only did Welles’s masterpiece change the face of film for every other reason in the book, but it also presented us with one of the first truly great antiheroes. Modelled not-so-subtly on William Randolph Hearst, Citizen Kane follows the life of Charles Foster Kane from financially lacking child to billionaire a- -hole. We see his career pass from strident idealism to selfish greed; moving from kindness and compassion to cruelty and loneliness. His dying word of “Rosebud” frames the story, as we seek to understand its meaning over the course of his life. Kane’s professional ascent mirrors his personal descent, as we learn the golden truth: his dying thought was one of nostalgia and regret for his youth, as simple, loving, and poverty-stricken as it was. Titling his film “citizen” Kane, Welles seems to strike at that deepest chord of the antihero: it could be any one of us.

Honourable mentions: Rick Blaine (Humphrey Bogart, Casablanca, 1942), Harry Callahan (Clint Eastwood, Dirty Harry series, 1971, 1973, 1976, 1983, 1988), Han Solo (Harrison Ford, Star Wars trilogy, 1977, 1980, 1983)