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10 Essential Cinematic Antiheroes

by Jessica Kiang
April 25, 2013 3:48 PM
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The Social Network Jesse Eisenberg

Mark Zuckerberg (Jesse Eisenberg) in David Fincher's "The Social Network" (2010)
Lest for a moment you think all antiheroes have to lose, let's talk about one who wins, and wins big. Mark Zuckerberg, as portrayed by Jesse Eisenberg in "The Social Network," is a textbook example of the guy you dislike, who you kind of hope to see brought low by his hubris and self-importance, but then that poetic thing happens where his self-importance is proven to have had actual foundation, and so actual importance (and wealth and fame and all the trappings) follow. The sharp, satirical bent of Aaron Sorkin's script and the leanness of David Fincher's direction took what could simply have been a biopic, or a topical news story-turned-movie, and turned it instead into something vital and unnerving -- a comment on our modern times, and a pretty scathing one at that. But it's Eisenberg's Zuckerberg who is the great creation here, by turns manipulative and Machiavellian, and then socially inept and pathetic -- he's the ultimate loser-who-wins. And at the heart of his psychology is the fascinating push-pull shared by many of the antiheroes on our list: a broad streak of self-loathing that manifests itself as self-love. So perhaps that's the reason the character still passes the Pupkin test: we might covet his power and influence and ludicrous wealth, but would any of us really want to wake up in the morning and be that character (not the real-life guy; that's another question), with all the mortifications and pettinesses and jealousies we read into him?

Talented Mr Ripley Matt Damon

Tom Ripley (Matt Damon) in Anthony Minghella's "The Talented Mr. Ripley" (1999)
A recurring feature of many of the entries on this list is that our antiheroes are themselves in the throes of some kind of hero worship. Something about seeing how they fall drastically short (often in their own eyes) of the standards of the person they aspire to be highlights their antiheroic qualities: where their idol is successful, they are failures; where he is popular, they are outcasts; where he is glamorous, they are mundane. And having their dazzled adoration of their hero turn bitterly in on itself is where many of these films derive their dark power. Rupert Pupkin and Jerry Langford fit this model, as do Robert Ford and Jesse James, as do Sidney Falco and J.J. Hunsecker (more on those latter two below). But one version who sprang from the written page was Tom Ripley, Patricia Highsmith's amoral, creepy chameleon, who's been brought to the screen by John Malkovich, Barry Pepper, Alain Delon, Ian Hart, Dennis Hopper and Jonathan Kent, but is best known to general audiences as played by Matt Damon in Anthony Minghella's "The Talented Mr. Ripley." Damon's Tom is a classic antihero, an amoral, blank slate whose only real characteristics are a sense of his own inadequacy and a desperate desire, not just to be with someone unattainable, but to actually be them -- in this case golden boy Dickie Greenleaf (Jude Law). Tom's covetousness of Dickie eventually turns murderous but it's the knowledge that Greenleaf is just one in a series that really chills: Ripley's is a hunger that can never truly be sated, and at his core is an emptiness that can't be filled.

Brighton Rock Attenborough

Pinkie Brown (Richard Attenborough) in John Boulting's "Brighton Rock" (1947)
Forget the rather plodding recent remake with Sam Riley in the role, the Pinkie Brown who left the most indelible mark on us was Richard Attenborough in the 1947 British film directed by John Boulting. Based on Graham Greene's novel of the same name, the film features the astonishingly blackhearted Pinkie as the sudden de facto leader of a small gang of thugs who terrorise the eponymous seaside town. Murdering to cover up murders, and blackmailing and vicitmizing everyone he comes across, it's in his treatment of Rose, the misguided dope of a girl who falls for him, that Pinkie's character is most tellingly drawn. He fools her into marrying him so she can't testify against him, and is only prevented from offing her too by the eleventh-hour intervention of the police. So far, so cut-and-dried villain, but while Attenborough's Pinkie is undoubtedly that, what brings him back from caricature are the hints we get of his psychology -- a self-hating but devout Roman Catholic, Pinkie is not amoral, but actively immoral, and believes he's hell-bound. And as wicked as he thoroughly, undoubtedly is, the story puts us into a strange line of empathy with him, as contrasted with the petty somnambulism of the seaside town and the pleasure-seekers it attracts. Not to mention the abrasive and crude Ida (Hermione Baddely) whose moral "decency" (she tries to get him brought to justice) manages to come off as vulgar and small-minded. No, Pinkie is despicable, all right, but his character has complexities and contradictions that make him worthy of such fertile characterization, and of our fascination.

The Master, Joaquin Phoenix

Freddie Quell (Joaquin Phoenix) in Paul Thomas Anderson's "The Master" (2012)
There are some directors who make the antihero their stock in trade, and we'd put Paul Thomas Anderson at the top of that list. We could have chosen any number of his characters: Paul Dano and Daniel Day-Lewis's characters both qualify from "There Will Be Blood" (Eli Sunday is the more obviously snivelling, but Daniel Plainview is a towering, raging antihero, too); Adam Sandler in "Punch Drunk Love"; most characters in "Magnolia" and "Boogie Nights"; indeed, we can go all the way back to John C. Reilly in "Hard Eight." So with this wealth of choice, we went for the most recent, and in a way most archetypal: Joaquin Phoenix's fearless turn as Freddie Quell in "The Master." Spiritually, mentally and emotionally broken (by which we mean shattered to smithereens) Quell's volatility puts him almost beyond the reach of relatability, until he does yet another unexpected thing and takes the "help" offered to him by self-styled guru Lancaster Dodd (Philip Seymour Hoffman). As their fractured relationship spirals away from simple mentor/protege into something odder and less definable, with each somehow coming to define the other in questionable, unhealthy ways, Quell's deep well of longing and hurt is gradually revealed, providing no excuses, but partial reasoning for his actions. It's a relationship that must end, and can never really end in Quell's favor as the balance of power is so thoroughly against him. And yet by the end, though there's an even greater gulf between their circumstances than before, we feel that perhaps the only real difference between them is that Dodd believes he's sane while Quell knows that he is not. Quell loses on every conceivable level, and we can't stop watching.

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  • NWOS | June 30, 2013 4:38 PMReply

    You are wrong to say that antiheroes are not cool.

    For one, many antiheroes, including Benjamin Braddock (who is undeservedly snubbed) or Jim Stark are only judged to be cool as the values or mores of society shift.

    For a great example of this read Ebert's two reviews of The Graduate, one he made as a young man and another 30 years after that. His opinions of Braddock's actions change as his values begin to align not with counterculture but with mainstream culture.

    Basically, an antihero often embodies a sub- or counter-culture because their values are seen as threatening or preverse, but when that culture becomes mainstream, the antihero is seen as cool after the fact. By ignoring this, you've left out countless antiheroes, whose image has changed to be viewed in a more favorable light.

  • kindred spirit | May 4, 2013 4:04 PMReply

    Good call on Mavis in Young Adult. But you seem to have forgotten Nicole Kidman in To Die For. Talk about a classic antihero!

  • PatrickNell | April 30, 2013 9:11 PMReply

    Wait, I'm confused. "The Pupkin Rule"? So every character I wouldn't want to be is an anti-hero? That makes no sense. I think you're confusing your terms. As I read the comment section I realize more intelligent commenters are making more reasonable cases but something is definitely off in this post. In classical and earlier mythology, the hero tended to be a dashing, confident, stoic, intelligent, highly capable fighter and commander with few, if any, flaws. The classical antihero is the inversion of this. Where the hero is confident, the antihero is plagued by self-doubt. Where the hero is a respected fighter, the antihero is mediocre at best. Where the hero is brave and courageous, the antihero is frightened and cowardly. Where the hero gets all the ladies, the antihero can't even get the time of day. In short, while the traditional hero is a paragon of awesomeness, the classical antihero suffers from flaws and hindrances. Jessica Kiang's definition is "any unlikable character in cinema"... <That is such an juvenile way to put it. I mean, the biggest fault in this blog-post is the list itself. Young Adult? Jessica, you think Theron in Young Adult is among the 10 Essential "Antiheros" in Cinema History? Fire this girl right now from The Playlist...hahaha... usually The Playlist's blog-posts have some intellect in them... this post assumes the reader is a dumb film fan. I am insulted to read this as a film lover. Thank you, bye.

  • Fordwsh | April 30, 2013 8:50 PMReply

    Reading this article and the comment section made me sick to my stomach. Are you all ill-begotten feeble-minded ninny's masquerading as film-buffs? Or do you all actually agree with this idiotic definition of "Antihero" being an unlikable character. This is an insult to all film-buffs worldwide, not to mention the intellectual film-goer. This article and these people who agree with it are the reasons why American cinema is at one of it's lowest points and only declining. Please, educate yourself before making a fool of yourself on the world wide web... This article is a miscarriage. I lost many respects for The Playlist for allowing this to be published. Lost a couple credibility points in my book but hey, at least you're succeeding in further stupidifying the average film-goer.

  • Dr PTA | April 30, 2013 9:01 PM

    @FORDWSH: Don't bother. You can't convince the stubborn-novice cinephile. They are a lost cause. I, along with many of my fellow cinephile -writer-friends saw this post and laughed at the authors misuse of the term and the list itself is unarguably a childish list. You can clearly see the authors misuse of the term antihero simply by taking a look at her list, it's that clear. One glance of the list and I left the page out of embarrassment for this blog but only returned to see if the author had given elaboration in the comment section, which she didn't... (another sign of amateurism) ... the author of this article surely needs to find a new profession. She writes well... but her intellect is on par with Esquire or People magazine..

  • Xian | April 30, 2013 4:30 PMReply

    Good list; great definition. I would add that the performance should be absolutely cringeworthy... like watching Ricky Gervais as David Brent in the original "The Office." So, for those of you that have or have not seen the minor film (though some call it a masterpiece of sorts), "Cutter's Way," I submit John Heard's performance as the eponymous Vietnam vet, Alex Cutter. (Can't paste a YouTube clip here, but search for "Cutters Way It Was In My Driveway" for a sampling of Heard's acting chops). Heard seemingly channels poet Charles Bukowski in bringing the acid-tongued, stream-of-consciousness ramblings of Cutter to life. It's probably Heard's best performance, and he plays off Jeff Bridges in a way that nearly (but certainly does not) make him likable. He's a bastard, an honest asshole, moving beyond mere curmudgeon into a mean ol' sonofabitch... but because of, and by the end in spite of, his nature, he digs deep into a murder mystery that takes him into the even weirder, meaner halls of the disgustingly rich.

  • JRDonug | April 28, 2013 4:41 PMReply

    According to the author of this article and everyone who agrees with her definition of "anti-hero"... An "anti-villian" would be any character in cinema history you love/like or wish you could "be"... I hope this comment brings understanding to people who are being led to believe a false cinematic term by the novice writer of this article. I wish there was some way a more experienced/intelligent cinematic writer could re-vamp this travesty of writing/list-making haha. Thank you!

  • Hughey Bifouf | April 28, 2013 12:19 AMReply

    The one inclusion I'd deem as the most warranted: Isabelle Huppert in The Piano Teacher.

  • DG | April 26, 2013 12:20 PMReply

    What about Reese Witherspoon in Election?

  • Xian | April 30, 2013 4:52 PM

    Redact: Because, Mavis.

  • Xian | April 30, 2013 4:32 PM

    Yeah, this list has no females, and yet... some of the best antiheroes according to The Playlist's definition are antiheroines. Good choice on Witherspoon's "Election" turn... a solid performance that makes the character seem cringeworthy and very real.

  • John | April 26, 2013 11:58 AMReply

    Completely agree that, by your own definition, Freddie Quell wouldn't qualify as an anti-hero. And admission aside, you couldn't come up with more than one female antihero?

  • SL | April 26, 2013 2:11 AMReply

    Although I know it's impossible to think of every anti-hero, I feel like Patrick Bateman from "American Psycho" needs to be on this list.

  • DG | April 25, 2013 9:09 PMReply

    Agree with Freddy Quell but disagree with the assertion that most of P.T.A's protags are anti-heros, especially Sandler's Barry Egan. I think one of the defining characteristics of the anti-hero is the inability to change, grow, or learn anything from their actions, and Egan has an arc in Punch Drunk Love that finds him (heroically) transforming from an alienated, anxiety-ridden caricature to someone capable of triumphantly defending his love and striking fear into the hearts of his enemies. Daniel Plainview and Paul Sunday also seem like anti-heros on paper but in the greater context of the movie, and as the symbols of early, burgeoning American industry, they take on mythical proportions that too me places them, if not in the realm of heroism then at least into the canon of outsiders. Great article though, and another good reminder that I really need to check out Young Adult.

  • DG | April 25, 2013 9:09 PMReply

    Agree with Freddy Quell but disagree with the assertion that most of P.T.A's protags are anti-heros, especially Sandler's Barry Egan. I think one of the defining characteristics of the anti-hero is the inability to change, grow, or learn anything from their actions, and Egan has an arc in Punch Drunk Love that finds him (heroically) transforming from an alienated, anxiety-ridden caricature to someone capable of triumphantly defending his love and striking fear into the hearts of his enemies. Daniel Plainview and Paul Sunday also seem like anti-heros on paper but in the greater context of the movie, and as the symbols of early, burgeoning American industry, they take on mythical proportions that too me places them, if not in the realm of heroism then at least into the canon of outsiders. Great article though, and another good reminder that I really need to check out Young Adult.

  • JP G | April 25, 2013 8:50 PMReply

    Here's a tribute to the wonderful film that is: "The Friend's of Eddie Coyle".
    (No links allowed it seems. Go to YT and search for "Friends of Eddie Coyle Tribute Project"
    Yes, we are no Mitchum, Yates, Jordon or Keats but we loved the movie so much and wanted to do a project so...Also, what's wrong with exposing it to the modern audience? Hope many newer and older film buffs who missed it back in the day will get around to viewing this 1973 classic and read the George V. Higgins novel that 80% of the film's dialogue is sourced from. Responsible comments welcome. Thanks!

  • JP G | April 25, 2013 9:01 PM

    *Meant to type: "Friends" of Eddie Coyle.... The lost discipline of proof reading. :-)

  • oogle monster | April 25, 2013 8:46 PMReply

    Playlist, I know we get in arguments from time to time but I forgive you for everything seeing that you put Charlize Theron's career second-best performance on this list. THANK YOU! Young Adult is such a great film.

  • Noah | April 25, 2013 8:40 PMReply

    Naked does not begin with a rape. Watch the scene again. Mike Leigh has dismissed this many times.

  • TheoC | April 25, 2013 6:50 PMReply

    The writer puts in a disclaimer/explanation of the parameters for inclusion on the list, commentors bitch about the reasoning?? Read the thing.

    Superb list well written. Affleck's Robert Ford creeps me the fuck out.

  • Shalala | April 25, 2013 8:23 PM

    Well I've read the "thing" and it's surely a well-written article, but the author is using a well-known and well-understood term (that's been understood for decades) and re-defining it as "a character you don't like"... or... "a character you don't love." The list is quite silly in and of itself, evident of a novice film-buff. Aside of the aforementioned absentees, where's Clint in Unforgiven? Min-sik Choi in Oldboy? <2 I'd strongly consider. Hope the author understands she has published an amateur article disguised as a well-written piece... :\ She's probably new to the PLAYLIST... much to learn!

  • droop | April 25, 2013 6:39 PMReply

    you clearly didn't understand the master, freddie quell is no antihero and certainly does not belong on this list, and your assessment of him and the movie are just so off the mark. he absolutely has virtues. he is kind, loyal, courageous and humble. the worst

  • Andrew | April 25, 2013 6:07 PMReply

    The King of Comedy is my favorite Scorsese film.

    And glad to see I'm not the only one who views Casey Affleck's performance as Robert Ford one of the absolute greats of recent memory. I mean, geez, it's one of my favorite performances of all-time.

  • yer | April 25, 2013 5:46 PMReply

    The King of Comedy is such an underrated film. An excellent companion piece to Taxi Driver and features one of De Niro's finest performances.

  • wes | April 25, 2013 4:47 PMReply

    I can't bring myself to watch Naked even though it's sitting in my Netflix queue.

  • Ummmm | April 25, 2013 4:37 PMReply

    Your list is missing the essential anti-hero in cinema history: Jake Gittes in Chinatown. Also good mentions could have been Hackman in The Conversation, or Gould in The Long Goodbye. No offense to the author but... this list is rubbish.

  • ORO | April 29, 2013 11:04 PM

    Actually I take that back. I redact my statement. I did some further research and realized UMMMM was closer than I thought. The author of the article is a bit off in her definition. This whole article/comment is a bit sticky. Makes me question peoples credibility/gullibility these days. Where are the intelligent cinephiles at? UMMMM at least makes an intelligent and intriguing counter argument. The author has no retort? Pity...

  • Oro | April 29, 2013 5:19 PM

    Actually, if you look up the definition/history of the term, it's much closer to that described in the article than that which you've described in your comment.

  • UMMMM | April 25, 2013 4:59 PM

    And yes, I read *your* definition of an "anti-hero"... which is basically just unlikeable characters. Not the true meaning of anti-hero. By your logic - Every unlikeable character is an anti-hero or yet, every character in history not portraying heroic qualities is an anti-hero. The point of the term anti-hero is supposed to be attached to characters that go against the conventions of the "hero" and are flawed/troubled. It's what Alan Moore/Frank Miller brought to Comic Books in 1986, and what Jake Gittes/Harry Caul are to perfection. The fact that your bending the definition to your own benefit allowing Theron from Young Adult onto this list is absurd.

  • Chris | April 25, 2013 4:29 PMReply

    What about Vincent Gallo in Buffalo '66??

  • Xian | April 30, 2013 4:18 PM

    Indeed... he's very much the antihero by Playlist's definition. Totally cringeworthy performance.

  • Todd | April 25, 2013 4:13 PMReply

    A sizeable chunk of Jack Nicholson films (Five Easy Pieces, Cuckoo's Nest, etc...)

  • JP G | April 25, 2013 8:43 PM

    Oops. I meant to say that I agree with Harley Quinn's reply to Mr. Todd's initial comment.

  • JP G | April 25, 2013 8:42 PM

    Agree with Todd. It's almost like Nicholson forced his way into the article's definition of "anti-hero" in many of his roles or that it is just what we came to expect of him. In the case of the former, it's like when one tries to be funny, they aren't as funny as they are when not trying. :-)

  • Harley Quinn | April 25, 2013 5:58 PM

    I agree that in my opinion many of Jack's roles are anti heroes, but he just makes them all too cool, at least for this particular list.

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