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My greatest regret is that I’m not a sociopath. I suspect I’m not alone. I have written before that we live in the age of awkwardness, but a strong case could be made that we live in the age of the sociopath. They are dominant figures on television, for example, and within essentially every television genre. Cartoon shows have been fascinated by sociopathic fathers (with varying degrees of sanity) ever since the writers of The Simpsons realized that Homer was a better central character than Bart. Showing that cartoon children are capable of radical evil as well, Eric Cartman of South Park has been spouting racial invective and hatching evil plots for well over a decade at this point. On the other end of the spectrum, the flagships of high-brow cable drama have almost all been sociopaths of varying stripes: the mafioso Tony Soprano of The Sopranos, the gangsters Stringer Bell and Marlo of The Wire, the seductive imposter Don Draper of Mad Men, and even the serial-killer title character of Dexter. In between, one might name the various reality show contestants betraying each other in their attempt to avoid being “voted off the island”; Dr. House, who seeks a diagnosis with complete indifference and even hostility toward his patients’ feelings; the womanizing character played by Charlie Sheen on the sitcom Two and a Half Men; Glenn Close’s evil, plotting lawyer in Damages; the invincible badass Jack Bauer who will stop at nothing in his sociopathic devotion to stopping terrorism in 24—and of course the various sociopathic pursuers of profit, whether in business or in politics, who populate the evening news.

On a certain level, this trend may not seem like anything new. It seems as though most cultures have lionized ruthless individuals who make their own rules, even if they ultimately feel constrained to punish them for their self-assertion as well. Yet there is something new going on in this entertainment trend that goes beyond the understandable desire to fantasize about living without the restrictions of society. The fantasy sociopath is somehow outside social norms—largely bereft of human sympathy, for instance, and generally amoral—and yet is simultaneously a master manipulator, who can instrumentalize social norms to get what he or she wants.

It is this social mastery that sets the contemporary fantasy sociopath apart from both the psychopath and the real-life sociopath. While many of the characters named above are ruthless killers, they are generally not psychopathic or “crazy” in the sense of seeking destruction for its own sake, nor do they generally have some kind of uncontrollable compulsion to struggle with. Indeed, they are usually much more in control of their actions than the normal “sane” person and much more capable of creating long-term plans with clear and achievable goals.

This level of control also sets them apart from a more clinical definition of sociopathy. I do not wish to delve into the DSM or any other authority in the field of psychology, where the usefulness of sociopathy as a diagnostic category is in any case disputed. Yet as I understand it, real-life sociopaths are pitiable creatures indeed. Often victims of severe abuse, they are bereft of all human connection, unable to tell truth from lies, charming and manipulative for a few minutes at most but with no real ability to formulate meaningful goals. The contemporary fantasy of sociopathy picks and chooses from those characteristics, emphasizing the lack of moral intuition, human empathy, and emotional connection. Far from being the obstacles they would be in real life, these characteristics are what enable the fantasy sociopath to be so amazingly successful.

It is curious to think that power would stem so directly from a lack of social connection. After all, we live in a world where we are constantly exhorted to “network,” to live by the maxim that “it’s all about who you know.” Yet the link between power and disconnection is a persistent pattern in recent entertainment, sometimes displayed in the most cartoonish possible way. Take, for instance, Matt Damon’s character in the various Bourne movies (The Bourne Identity, The Bourne Supremacy, and The Bourne Ultimatum— soon to be followed, as Damon has joked, by The Bourne Redundancy). In the first film, Jason Bourne is fished out of the ocean with no idea of who he is. As the story unfolds, he finds that he is unexpectedly the master of everything he tries to do: from hand-to-hand combat, to stunt driving, to speaking apparently every language on earth. His skills apply interpersonally as well, as the very first woman he meets (Franka Potente) becomes his partner in crime and then lover.

The narrative explanation for Bourne’s near superhero status is an elite CIA training program. Yet that training is directly tied to Bourne’s amnesia, as the program’s goal is to create the ultimate “sleeper” agents. The program culminates with a thorough brainwashing, after which the agents don’t remember they’re agents until their programming is triggered by some signal. The life the CIA sets up for the agent is, in true sociopathic style, only an act that can be left behind at any time. What’s more, a later film reveals that Bourne’s trainers only regarded him as truly ready to work once they had induced him to kill in cold blood someone he believed to be an innocent man. Lack of social ties and ruthless amorality thus fit together seamlessly with virtual superpowers in this movie.

The pattern isn’t limited to superheroes. For instance, Don Draper of Mad Men, arguably the most iconic and exemplary contemporary TV sociopath, becomes a powerful ad executive who appears to do little but drink all day and wait for random flashes of inspiration. And as if securing a wife who looks like Grace Kelly isn’t enough, he repeatedly seduces interesting, substantial women, because for most of the series’ run, the standard route of seducing naïve young secretaries is simply beneath him. What enabled this miraculous rise? Stealing the identity of a man who has literally just died in front of him and then abandoning his family!

Many of these sociopathic characters are, of course, “psychologically complex,” particularly in shows with high-brow ambitions. Don Draper is never sure what he wants, though he nearly always gets it, and Tony Soprano famously seeks out therapy to help him deal with the stress of being a mob boss. Dexter gets a voiceover where he muses about what it must be like to feel sympathy or happiness or sadness, while House is subjected to endless amateur psychoanalysis by his friends and co-workers, distraught about how he can be so rude and cynical.

It is hard to believe, however, that the exploration of the dark side of the human psyche for its own sake is behind the appeal of these sociopathic characters. What, then, is going on in this trend? My hypothesis is that the sociopaths we watch on TV allow us to indulge in a kind of thought experiment, based on the question: “What if I really and truly did not give a fuck about anyone?” And the answer they provide? “Then I would be powerful and free.”

In order to get at why this thought experiment would be appealing, and even more why this somewhat counter-intuitive answer would be compelling, I believe it will be helpful to take a detour through awkwardness.

At first glance, the TV sociopath appears to be nearly the opposite of the awkward character. I’ve previously defined awkwardness as the feeling of anxiety that accompanies the violation or absence of a clear social norm. It could happen when someone commits a social faux pas, such as telling a racist joke (what I’ve called “everyday awkwardness”), or it could occur in situations where there are no real social expectations to speak of—for instance, in cross-cultural encounters where one cannot appeal to a third “meta-culture” to mediate the interaction (what I’ve called “radical awkwardness”). In both cases, we are thrown into a situation in which we don’t know what to do. At the same time, however, this violation or lack of social norms doesn’t simply dissolve the social bond. Instead, awkwardness is a particularly powerful social experience, in which we feel the presence of others much more acutely—and more than that, awkwardness spreads, making even innocent bystanders feel somehow caught up in the awkward feeling. This “raw” feeling of social connection can be so anxiety-producing, in fact, that I have even hypothesized that awkwardness comes first and social norms are an attempt to cope with it.

In contrast to the sociopath, then, whose lack of social connection makes him or her a master manipulator of social norms, people caught up in awkwardness are rendered powerless by the intensity of their social connection. Thus we might say that at second glance, the TV sociopath is the exact opposite of the awkward character—the correspondence is too perfect to ignore.

To understand why this connection might exist, I’d like to look more closely at my distinction between the violation and the lack of a social norm. The distinction between these two situations is not hard and fast, because in many cases, it’s not clear how to react to the violation of a social norm. Many social norms function as straightforward commandments—for example, “thou shalt not take cuts in line”—but fail to prescribe a punishment or designate an agent who is qualified to administer it. As a result, when someone does take cuts, there seems to be nothing anyone can do.

In fact, the person who does decide to confront the offender may well come out looking like the asshole in the situation, because in many cultural settings there is a strong bias against unnecessary confrontation. The awkward person sits and fumes, or else confronts the cutter and quickly retreats. If we could define something like the everyday sociopath, it would be the person who is not only callous enough to take cuts in the first place, but is able to manipulate social expectations to shame the person who calls out the violation.

The transition to the fantasy of TV sociopathy comes when the awkward person shifts from “I hate that guy” to “I wish I were that guy.” In everyday settings, this shift is unlikely. Even if the line is unbearably long, most well-adjusted people would prefer not to disobey their ingrained social instincts and, if confronted with a queue-jumper, would console themselves with the thought that at least they are not such inconsiderate people, etc. Similar patterns repeat themselves in other areas of life—a man may wish, for instance, that he were a suave seducer, but at bottom he feels that the seducer is really a douche bag. Even though envy is probably inevitable, a feeling of moral superiority is normally enough to stave off outright admiration of the everyday sociopath.

In order to get from the everyday sociopath to the fantasy sociopath, we need to think in terms of my third class of awkwardness, which I’ve called cultural awkwardness, but perhaps should have called culture-wide awkwardness. Falling in between the types of awkwardness stemming from a violation and a lack of a social norm, cultural awkwardness arises in a situation where social norms are in the process of breaking down. Just as it’s easier to criticize than to create, a social order in a state of cultural awkwardness is perfectly capable of telling us what we’re doing wrong—but it has no convincing account of what it would look like to do things right. My favorite encapsulation of this Kafkaesque logic remains a quote from Gene Hackman’s character in Royal Tenenbaums: “It’s certainly frowned upon, but then what isn’t these days?”

In Awkwardness, I argued that the proper response to our culture-wide awkwardness is simply to embrace rather than try to avoid awkwardness. After all, if the social bond of awkwardness is more intense than our norm-governed social interactions, it also has the potential to be more meaningful and enjoyable. Such a strategy sacrifices comfort and predictability, but it’s not clear that comfort and predictability in our interactions are always desirable anyway.

What our cultural fascination with the fantasy sociopath points toward, however, is the fact that the social order doesn’t exist simply to provide comfort and predictability in interpersonal interactions. One would hope that it might also deliver some form of justice or fairness. The failure to deliver on that front is much more serious and consequential than the failure to allay our social anxieties, though the pattern is similar in both cases. In a society that is breaking down, the no-win situation of someone flagrantly cutting in line repeats itself over and over, on an ever grander scale, until the people who destroyed the world economy walk away with hundreds of millions of dollars in “bonuses” and we’re all reduced to the pathetic stance of fuming about how much we hate that asshole—and the asshole also has the help of a worldwide media empire (not to mention an increasingly militarized police force) to shout us down if we gather up the courage to complain.

At that point, the compensation of moral superiority no longer suffices. We recognize our weakness and patheticness and project its opposite onto our conquerors. If we feel very acutely the force of social pressure, they feel nothing. If we are bound by guilt and obligation, they are completely amoral. And if we don’t have any idea what to do about the situation, they always know exactly what to do. If only I didn’t give a fuck about anyone or anything, we think—then I would be powerful and free. Then I would be the one with millions of dollars, with the powerful and prestigious job, with more sexual opportunities than I know what to do with. In short order, it even comes to seem that only such people can get ahead.

This interpretation has much to recommend it. The people who run our world do a lot of terrible things, and the highest level of contrition they display is seldom more than a token gesture—in fact, officials regularly “take full responsibility” for things without suffering any apparent consequences at all. It takes a special kind of person to order the invasion of a country with no provocation, to cut social programs that millions rely on in order to meet the demands of bondholders, or to deprive people of their livelihood because a set of numbers isn’t adding up in the right way. One can easily argue that the various managers and administrators who control our lives are overpaid, but the callousness they routinely display really does represent a rare skill set. I know that I couldn’t cope with the guilt if I behaved like them—right?

Yet perhaps I could. Perhaps the problem isn’t that we’re being ruled by sociopathic monsters, but rather by people who are just as susceptible to social forces as the rest of us. One might think here of the frequently observed phenomenon of people being perfectly nice one-on-one, but obnoxious and unbearable when part of a group—something often associated with gender-segregated adolescent groups.

Individual members of a fraternity or sports team, for example, might be uncomfortable with the way they are expected to behave toward women—they might have a less constrained view of who counts as “attractive” or be uncomfortable with hook-up culture—but they conform in order to avoid getting made fun of by the other guys. And why will those other guys make fun of them? Because they will be made fun of if they take the non-conformist’s side. The dynamic whereby these young men have to continually prove that they’re “real men” or else face ostracization doesn’t require any individual young man to be a bad person going in. And though the addition of a genuinely malicious person might exacerbate the problem, the dynamic is basically self-sustaining without the need for any external “evil” inputs.

Similar dynamics obviously happen in the corporate and political worlds as well, particularly in light of how insular those social circles can be. A politician must be willing to make “tough choices”—and somehow that tough choice is always somehow related to piling further burdens on the already disadvantaged. Of course no one wants to be a bleeding heart, or an idealist, or a wimp, and so no one seriously pushes back. Yet all these spineless conformists style themselves, à la John McCain, as straight-shooting mavericks who aren’t afraid to tell it like it is.

For every average Joe saying to himself, “I wish I was like Tony Soprano,” then, there’s a member of the ruling class saying to himself, “You know, I am kind of like Tony Soprano—it’s not always pretty, but I do what needs to be done.” What both fail to recognize is that Tony Soprano’s actions are no more admirable or necessary than the decision to exclude some poor schlub from the in-group on the playground. More fundamentally, both fail to recognize that what is going on is a social phenomenon, a dynamic that exceeds and largely determines the actions of the individuals involved—not a matter of some people simply being more callous or amoral (though some people certainly are) or being more clear-eyed and realistic (as few of us really are in any serious way).

The fantasy of the sociopath, then, represents an attempt to escape from the inescapably social nature of human experience. The sociopath is an individual who transcends the social, who is not bound by it in any gut-level way and who can therefore use it purely as a tool. The two elements of the fantasy sociopath may not make for a psychologically plausible human being, but they are related in a rigorously consistent way.

Indulging in the fantasy of the sociopath is thus the precise opposite of the strategy of indulging in the primordial social experience of awkwardness. Both approaches, however, respond to the same underlying reality, which is a social order that is breaking down, making impossible demands while failing to deliver on its promises.