10 Great Self-Absorbed, Narcissistic Movie Assholes

"The characters aren’t sympathetic enough," goes one of the most popular, and most-derided, notes perpetually sent from executives to filmmakers. And in certain movies, likability is a factor, but we’d rather spend time with three-dimensional characters who were interesting, authentic and human, rather than simply blandly nice, and there’s something particularly fascinating about the self-absorbed, narcissistic, unrepentant asshole.

There’s more than a few examples of the archetype doing the rounds at the moment, from the three lovably awful kids in Amazon’s brilliant "Transparent" to the title character of Alex Ross Perry‘s brilliant "Listen Up Philip," which opened in limited release last Friday and will continue to expand in the coming weeks. Said archetype is of course often complex, and "asshole" frequently doesn’t cover it. These characters often are masking deep pain, insecurity, self-doubt and or misplaced arrogance. But we know these types and while often not likable, they’re real and often quite hilariously awful.

So, to mark the release of "Listen Up Philip," which features a deliciously prickly Jason Schwartzman in the lead as a egocentric young writer who damages all his relationships, romantic or otherwise, we thought we’d pick out ten of our favorite self-absorbed, unpleasant and yet curiously watchable characters to go alongside his great turn in the aforementioned film. It should be noted that most of our examples come from the last decade or two, but that’s not entirely surprising, given that we’re arguably living in the most self-obsessed, insular age in human history (this is of course the era of the selfie). Take a look at our picks below, and let us know your favorites in the comments section.

Sean Penn as Emmett Ray in “Sweet & Lowdown” (2000)
Woody Allen is an obvious touchstone for "Listen Up Philip" ("Husbands And Wives" is named specifically by Ross Perry, and Sydney Pollack‘s character in that arguably qualifies for this list too), and Allen’s certainly representative of self-absorption. But none of his creations have been more self-absorbed, or more asshole-y, than Sean Penn‘s central figure  in "Sweet & Lowdown."  The role of Emmet Ray, a reasonably well-known, heavy-drinking, scumbag of a jazz guitarist whose life is continually overshadowed by that of his idol Django Reinhardt, was originally penned by Allen (under the original title of "The Jazz Baby," back in the early 1970s) to be played by the writer/director, but after nearly thirty years in a drawer, went to Penn (though Johnny Depp was also reportedly considered). And it’s hard to imagine anyone doing a better job. Penn brings a mix of swagger and deeply insecure neuroticism that makes him very much a creation of Allen, but one that doesn’t simply echo the filmmaker in the manner of so many of his leading-men surrogates. As with the lead of another later film about a guitarist, the Coens’ "Inside Llewyn Davis," Ray is talented, but enough of a fuck-up (drunken, a sometime pimp, kind of a coward, tight with money, and with a self-inflated view of his own "genius") that he’ll never make the kind of impact that he’d like to. And when potential redemption comes along in the shape of Samantha Morton‘s sweet, mute Hattie, he throws it away in order to marry socialite Uma Thurman. And when he’s dumped by her, he’s stunned when Hattie’s moved on. He’s almost irredeemably awful, and yet Penn’s performance, one of his very best, manages to find pathos, as well as a pleasing level of comedy, in the character, the kind of thing the actor doesn’t get to do enough.

Bill Murray as Steve Zissou in "The Life Aquatic With Steve Zissou" (2004)
Wes Anderson characters can generally be grouped under the banner of "self-regarding" to one degree or another, from Max in "Rushmore" to even the animated Mr. Fox. But his prize asshole might just be Steve Zissou, in Anderson’s fourth film. An oceanographer and documentary maker modelled loosely after Jacques Cousteau, Zissou is a man whose limited fame and prestige has gone very much to his head, who drags his inexplicably loyal crew on an Ahab-ish revenge trip against the shark that ate his long-time partner (Seymour Cassel). He has a certain affection for the people he travels with (he does at least launch a rescue mission when even hated insurance company employee Bud Cort is captured by pirates), but is resolutely unlovable otherwise, particularly in his relations with basically everyone, from consistently hitting on pregnant reporter Jane (Cate Blanchett), treating Klaus (Willem Dafoe) like a bullied lapdog, or feuding childishly with his maybe-son Ned (Owen Wilson), who’s eventually killed in a helicopter crash on the hunt for the shark. Anderson’s characters, even cantankerous assholes like Royal Tenenbaum, usually find some form of redemption, but there’s surprisingly little for Zissou: Ned, who turns out not to be his son anyway, dies, and Zissou is once again acclaimed at a film festival for his finished picture. It’s a decidedly sour note, and perhaps one of the reasons that the lavish, lovingly made ‘Aquatic’ is possibly Anderson’s least-loved picture.

Jesse Eisenberg as Mark Zuckerberg in "The Social Network" (2010)
"You’re going to go through life thinking that girls don’t like because you’re a nerd," says Rooney Mara‘s Erica to Mark Zuckerberg (Jesse Eisenberg) at the beginning of David Fincher‘s Aaron Sorkin penned "The Social Network." "And I want you to know, from the bottom of my heart, that that won’t be true. It’ll be because you’re an asshole." And it’s perfect introduction to the condescending, snobbish, ambitious, narcisisstic founder of Facebook, the website that will eventually make him a billionaire. And as the film goes on, Zuckerberg never exactly improves: he creates an insulting blog about Erica, hacks into Harvard’s network to steal photos of women to let people rate their attractiveness, possibly steals the idea for his site from a trio of other students, freezes out best friend Eduardo Saverin (Andrew Garfield), and ends up rich but estranged, endlessly refreshing his friend request to Erica. He’s selfish, self-regarding, prickly and defensive, but in the hands of Eisenberg’s meticulous, brilliant performance, you can also see why. He embodies the true revenge of the nerds, a twisted and bitter one, but he’s only that way because that’s what he thinks he has to be. As his attorney, Marylin (Rashida Jones) tells him at the film’s conclusion, "you’re not an asshole, Mark. You’re just trying so hard to be."

Kevin Kline as Otto in "A Fish Called Wanda" (1988)
Self-absorption is often something that seems to come with intellect, as demonstrated by the characters on this list. Many of these figures genuinely are the smartest person in the room and treat anyone they deem not to be on their level with according levels of contempt. Otto, in "A Fish Called Wanda," is something slightly different, and all the funnier for it:  he’s a moron who only thinks he’s the smartest person in the room. The result, unusually for a broad comedy like Charles Crichton‘s 1988 hit (penned by co-star John Cleese), won Kevin Kline a Best Supporting Actor Oscar. The character is the film’s secret weapon, a borderline psychotic, Limey-hating dimwit with a severe inferiority complex, which manifests in his continual threats to those around not to call him stupid. But as his lover Wanda (Jamie Lee Curtis) tells him, “I’ve known sheep that could outwit you. I’ve worn dresses with higher IQs.” Otto is a man who thinks “the Gettysburg Address was where Lincoln lived,” that the central message of Buddhism is “every man for himself,” and that the London Underground is a political movement. He’s the ultimate Ugly American abroad (“you are the vulgarian, you fuck,” he tells Cleese’s Archie when he calls him on his swearing), a terrible driver with the most hilarious off-putting cum face in cinematic history, and a total tour de force from Kline that still remains the actor’s finest hour. He’s the truly hateable kind of asshole in the best possible way. It says it all that, after somehow surviving being run over by a steamroller, he becomes Minister of Justice in apartheid-era South Africa…

Charlize Theron as Mavis Gary in "Young Adult" (2011)
Arguably Jason Reitman‘s best film to date, a brilliant gender-swapped inversion of the arrested-development theme that’s dominated the comedy movie in the last decade or so, "Young Adult" revolves around a titanic performance from Charlize Theron, playing one of the most unrepentantly unlikable, unchangeable characters in recent cinema. Theron, arguably in a career-best turn, plays Mavis, a divorced writer of the teen-aimed books whose series has just been cancelled. On a whim, she returns to her small Minnesota hometown in an attempt to win back her high-school sweetheart (Patrick Wilson), who’s just a had baby with his wife (Elizabeth Reaser). Mavis is clearly having some kind of deluded break with reality, but part of the brilliance of Theron’s performance is how unquestioning she is of herself: a Mean Girl grown up, chasing simpler times when she ruled the world, and prepared to do just about anything to get there. Theron never courts your sympathy, but there’s still a deep sadness in Mavis’ absolute lack of self-reflection, not least when she’s comes close to a breakthrough, only to be talked out of it by one of her few remaining admirers (a brilliant Colette Wolfe). People talked about her bravery in changing her appearance for her Oscar-winning turn in "Monster," but there’s just as little vanity in her performance here, and the film simply wouldn’t work without her.

The Assorted Jerks Of Noah Baumbach
Another obvious touchstone for "Listen Up Philip," Noah Baumbach is arguably, and we mean this in the nicest way possible, the king of the self-absorbed asshole. In fact, we decided to amalgamate his collected jerks into one selection, because otherwise it could have taken up half of the entire list. The filmmaker’s been interested in the archetype ever since his debut "Kicking And Screaming," about chronically procrastinating recent college grads, but (after co-writing the script for two of Wes Anderson‘s most self-absorbed characters with "The Life Aquatic" and "Fantastic Mr. Fox") reached something of a zenith with what we like to call ‘The Asshole Trilogy’ : "The Squid & The Whale," "Margot At The Wedding" and "Greenberg." ‘Squid’ is the best, as we gradually see the effects of self-absorbed, generally toxic novelist Bernard (Jeff Daniels) on his son (Jesse Eisenberg) during the parents’ bitter divorce, ending movingly with Walt rejecting the Way Of The Jerk. 2007’s ‘Margot’ was disliked by many at the time, but has only grown in stature, with Nicole Kidman‘s brittle, sharp turn proving to be a perfect fit for the filmmakers’ world-view, appalling (but still human) as she takes her frustrations in life out on her son. 2010’s "Greenberg" is the least of the three, despite a raw and uncompromising performance by Ben Stiller in the title role, a thwarted man-child who can’t see much beyond his own needs and worldview. The three films aren’t the easiest watch (no wonder that Baumbach’s next film, the delightful "Frances Ha," felt like such a breath of fresh air), but together do a pretty great job at encapsulating the era of mammoth selfishness.

Campbell Scott as Roger Swanson in "Roger Dodger" (2002)
Jesse Eisenberg makes another appearance on this list (his more malevolent side in the recent "The Double" could also have qualified), but for once, he’s not the asshole. That would be Campbell Scott, who is remarkably brilliant in Dylan Kidd‘s minor classic "Roger Dodger." Scott plays the titular Roger Swanson, a New York ad-man who’s asked by his 16-year-old nephew to help him learn how to seduce women so he can lose his virginity. Roger’s a self-described player and essentially a misogynist, and attempts to induct his young relative in what he describes as essentially a war of the sexes. A smarmy early ’00s precursor to today’s pick-up artist scumbags, Roger doesn’t have the charm that he thinks he does, particularly given that he’s in an unacknowledged meltdown after being dumped by lover/boss Isabella Rosselini. Like many such people, he hates almost everyone around him, but no one brings out quite so much bile in him as himself, and it’s this brilliant duality that makes the performance one of Scott’s best. Kidd’s film is a woozy, witty examination of sex and masculinity, and though it missteps a little towards the end in offering something of a redemption for the character, it still gave us one of the more iconic cinematic douchebags of the last couple of decades.

Anne Hathaway as Kym in "Rachel Getting Married" (2008)
We think of being an asshole as a specifically male trait, but we’ve already seen with "Young Adult" and "Margot At The Wedding" that there’s no gender divide. "Rachel Getting Married" is another great example, one that’s arguably sadder and psychologically richer than either. Jonathan Demme‘s film stars a revelatory Anne Hathaway as Kym, who returns home from drug rehab to attend the wedding of her sister (Rosemarie DeWitt), only for the family’s long-brushed-over painful past to emerge, as it tends to do in movies like this one. Kym initially seems like a comically awful person, a selfish, up-staging drug addict who hijacks the rehearsal dinner to make twelve-step apologies, and who seems to delight in deliberately upsetting almost anyone in her family and not accepting any blame for her actions. But over time, Kym richens, as we learn that she killed her younger brother in a car accident when she was high, and while that itself is clearly a terrible and selfish action, it’s only continued to haunt her, and Hathaway is superb in painting a picture of a woman who longs to be forgiven by people who would like to, but might just find it impossible. Demme and the movie never let her off the hook, but that whatever small progress she might make happens at all feels all the more moving for being so hard-won.

Jack Nicholson in "As Good As It Gets" (1997)
Ol’ Jack plays cantankerous assholes the way Tom Hanks plays nice guys or Tom Cruise plays people who jumps off tall buildings: brilliantly, vigorously and frequently. In James L. Brooks‘ award-winning rom-com, Nicholson builds on earlier performances like "Five Easy Pieces" "Carnal Knowledge" and "Heartburn" to create something like a crown prince of unlikable fellas, OCD-suffering, racist, homophobic, misogynist misanthrope novelist Melvin Udall, whose carefully controlled life is upended by the intervention of gay neighbor Simon (Greg Kinnear), and single-mother waitress Carol (Helen Hunt). Nicholson might be playing a slightly sitcom-ish, Archie Bunker-ish character, but the mix of his typical devilish charm, smartly and sparingly used, and a detailed psychological realism that makes Melvin into more than just an archetype, elevated the performance to Oscar-winning effect. Though of course it helps that Nicholson is clearly relishing the lovingly and intricately-written speeches that he gets to deploy ("never, never interrupt me, okay?," he tells Simon. "Not if there’s a fire, not even if you hear the sound of a thud from my home and one week later there’s a smell coming from there that can only be a decaying human body and you have to hold a hanky to your face because the stench is so thick that you think you’re going to faint"). There’s a certain degree of cheesiness to the way that Melvin softens up thanks to the love of a good woman, but Jack never makes you doubt it for a minute.

The Many Assholes Of Whit Stillman
Like Baumbach, Whit Stillman is a director who’s made a career with characters who can’t quite see past their own bubble of existence (and, usually, privilege), up to and including his current Amazon pilot "The Cosmopolitans." The pattern began with his debut "Metropolitan," in which Stillman favorite Chris Eigeman plays arguably the platonic ideal of the director’s favorite archetype, a big-mouthed upper-class cynic who one can imagine going into Wall Street and essentially becoming Patrick Bateman in years to come (‘"the surrealists were just bunch of social climbers," he condescendingly says at one point). Follow-up "Barcelona" sees Eigeman in a similarly smug role, the ugly American abroad, while "The Last Days Of Disco" sees Kate Beckinsale (who’s fantastic here) as a particularly callow example of the type ("remember the Woodstock generation of the 1960s that were so full of themselves and conceited? None of them could dance," she tells someone at one point with the naivety of youth). If one was ungenerous, one could argue that the narrow worldview of his films makes Stillman and his archaic language rather self-absorbed himself, but that’s a misreading: Stillman is ultimately a social satirist, a sort of cinematic heir to Jane Austen (whose influence is felt in his most recent picture, "Damsels In Distress," more than ever), savagely poking at the ridiculous attitudes and views of his characters without ever quite judging them.

Honorable Mentions: There were various other possibilities that we dismissed as not quite being quite the right brand of asshole for this specific theme: think of Kirk Douglas in "Ace In The Hole," Tony Curtis and Burt Lancaster in "Sweet Smell Of Success" (too toxic), even William Atherton in "Die Hard" and "Ghostbusters" (which veers closer to a simple villain). Among the ones who came closest to qualifying were Ed Norton and Micheal Keaton in "Birdman" (we wrote about their self-absorbed asshole-ish tendencies here), Rachel McAdams in "Mean Girls," Matt Damon in "The Departed," Paul Reiser in "Aliens," Aaron Eckhart in "In The Company Of Men," and Tom Hulce in "Amadeus," along with both Jason Schwartzman‘s villain, and arguably Michael Cera‘s hero, in "Scott Pilgrim Vs. The World." Any others? Let us know below.