What does the self-made man love?

He is a figure we're all familiar with, the auto-constructed man, especially as Americans. Someone from Nowhere decides that, using his inherent smarts or wits or ambition, he is going to be someone, make a difference, something like that.

And so we love stories like Kurt Warner's, the supermarket worker turned NFL legend. We love it in the stories our Presidents tell about themselves. George W. Bush, son of a President, self-proclaimed "C student," pinched pennies, with Laura's help. Obama came from a broken home, and never fully knew his father. Even Lincoln began his story in a log cabin.

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We love this kind of thing, the person who comes from nothing. It tells us that anyone from anywhere can make his mark in the American landscape—that anyone can change the world.

But what's it like to be on the other end? What happens if you spend your existence making yourself, only to look at your life and realize that you hate everything about it, everyone in it, that the position you're in embodies everything you hate?

Do you want to be the self you made?

Baz Luhrmann's serviceable, if lacking interpretation of The Great Gatsby would have us believe—in endless voice-overs that either inform the audience or remove the book's subtlety, depending on your perspective—that the self-invention of Gatsby (Leonardo DiCaprio was born to play this role) is all about Daisy. Tobey Maguire's Nick Carraway, in awe: "Everything—he did it all for Daisy." Gatsby's mansion and immaculate lawn, his ridiculous riches, the parties, the lavish extravagance, was all for Daisy (Carey Mulligan). He'd met her only five years earlier, but allegedly, at that point, he made up his mind to have everything—in service of getting Daisy.

Too bad for Luhrmann, then, that we're also taken back to Jay Gatsby's youth, when he was just James Gatz, son of dirt-poor Nebraskan farmers with nothing but a wooden shack to their name. Nick's take on the situation: "Gatsby didn't consider [his parents] to be his parents; not really. He would stare out of his roof up at the stars and dream of another life." Gatsby had made up his mind—long before he met Daisy—that his own dream of himself, of who he could be, trumped any connections to people around him.

Which provides context for the temper tantrum Gatsby throws when Daisy asks him to run away with her, a scene Luhrmann handles uncertainly, as it entirely contradicts the grand sweeping Romeo + Juliet-like love story he wants to tell. But DiCaprio understands: Gatsby is upset because more than simply wanting Daisy for his own, he is pursuing a vision of who he wants to be. He loves Daisy insofar as Daisy wants to live his life, in a castle with gates imported from an old Dutch monastery, a castle that staffs a distant relative of Beethoven as its resident musician, that has a bedroom with a literal wrap-around catwalk.

Without clearly understanding this core of Fitzgerald's tale, the movie can only flounder, not sure if Gatsby's a narcissist, a hopeless romantic, or an eternal optimist. Luhrmann tries hard to convince us, but the "all for Daisy" rhetoric stretches credulity a little too much.

It was for himself. What Gatsby loves is a dream of a world, one where he is king, the chosen one, the best—and one that, incidentally and perhaps accidentally, includes Daisy.

So when Nick declares that Gatsby was "the most hopeful man I'd ever encountered," he's not wrong. But what Gatsby dreamed, with a purity of vision unmatched by anyone else, was a dream of himself, a vision for himself, a life where everything orbited around the center construct of Gatsby.

This is a question of human nature. Can someone like Gatsby—because first and foremost, he's a type, a representation of the self-constructed man writ large—really love someone wholeheartedly? Can he really give himself away to someone else?

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And more: is it possible for Jay Gatsby to really love anyone, when he hates James Gatz so much? Can you love through your own self-rejection, self-loathing?

Gatsby is incoherent. He wants to love purely, but he also wants everyone else to love Jay Gatsby as much as James Gatz does. This makes Gatsby (consciously or not) a demonstrative example of the problems that are posed by the sort of existentialism cooked up by the French philosopher Jean-Paul Sartre, whose main thesis can be summed up with: "You can't remake yourself half-heartedly."

To Sartre, all of life was self-determined. You choose who you are and who you will be, who you will be with, what you will pursue, what you will achieve. Nobody can dictate that to you, and to submit to your society's expectations is to act inauthentically—something to be condemned. Sartre's solution to nihilism is to just keep existing: there is no overcoming the void, only struggling against it. (Sartre's compadre, Albert Camus, was fond of the myth of Sisyphus, the unlucky Greek doomed to roll a rock up the hill for all of eternity, only to have it roll down again every time. In Camus' retelling, Sisyphus could change his fate simply by choosing to take delight in the rolling.)

Choose who you are, what you want to be, and what you want. And then take it. To do anything else is incoherent, nonsensical, and cowardly. It'd be giving up.

And in all reality, Sartre's hero—one who eschewed happiness in favor of coherence, one who valued making sense more than feeling falsely "fulfilled"—would look identical to Mad Men's Don Draper, a character who has spent five (going on six) TV seasons pursuing his idea of a good life. But it has never fulfilled him, not once, even when it seemed it might.

As the epitome of a self-made man, Don Draper embodies the kind of success that might be possible for someone who took Sartre's conception of the universe seriously. He's respected, wealthy, sexy, and successful, and he can get any girl he wants. He has a great apartment and an even better liquor cabinet.

Mad Men has never been a show about a man pulling himself up by his bootstraps: it began with Don married to a beautiful woman, working as creative director of an ad agency, with lovely children and the respect of his colleagues. Since the pilot episode, Don has had it all. Every subsequent season has tried to trace out why Don is centrally incapable of loving anything. And the key to this is the fact that the only time we ever see Don happy and loving, it's when he's not Don Draper at all. Dick Whitman—Don's real name—is the son of a prostitute, who never knew his father, who grew up in crushing poverty. When the real Don Draper died fighting with Dick in the Korean War, Dick saw a chance to be different, to be everything Dick wasn't.

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But even after assuming the identity of Don Draper, becoming wealthy and powerful and successful, he went on to care for the dead Draper's wife. And it's only in his interactions with Draper's widow that we see him happy and relaxed—smiling, caring about someone else, actually able to love at all.

The difference is that Draper's widow sees and knows Don for exactly what he is: a lonely, broken man, scared that he'll be found out, scared that his illusion will come crashing down in front of everyone. Don believes he cannot be loved. When someone loves him—his own wife, for instance—he pulls back reflexively, like a hand from a hot stove; for the self-made man, to be loved is to be found out. And so Don is plagued by the same paradox that defines Gatsby; Don loves his own self-conception, but hates the reality of who he knows himself to be—that is, he loves Don Draper exactly as much as he hates Dick Whitman.

But Draper's widow asks nothing of Don. She needs him, but he needs her more, because she represents a safe place for him, somewhere that he can just be Dick Whitman: deserter, failure, faker, son of a whore. He cares for her not out of a sense of duty, but from gratefulness and responsibility. He sacrifices for her not for the sake of a love that begs for affirmation, that's only fulfilled in how it makes the lover look—but a love that gives itself away.

Don can't love those who love him—his children, his wives, his colleagues, his mistresses—for who they think he is: suave, capable, intelligent Don Draper. And similarly, James Gatz can't love Daisy unless she buys the whole package, the riches and charm, the glamour and the Euro-style castle. And that's the thing: you can't love others if you, at core, hate who you really are, and who you've chosen to become—because then they love someone unlovable (yourself), and are stupid and worthless for it, because they choose who to love poorly; and then they aren't worthy of love (in your own estimation), because you shouldn't love someone so stupid. It's a self-defeating principle: if you hate who you really are, you'll also hate anyone who loves you, because you're unable to overcome how wrong you think they are.

The trouble at root is this: Gatsby and Draper worship the image of Gatsby and Draper, and don't love the people around them. They chose, with the freedom afforded them by the American experiment, to remake themselves in their own image and likeness. They took the ideas Sartre espouses and just went for it, wholesale; they looked the void in the eye and decided to walk away. But they couldn't get away from their core, their soul, who they really were. The self-image they worshipped could never fully eclipse the self-loathing that prompted them to re-create themselves in the first place.

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Someone troubled, but brilliant—the writer David Foster Wallace—openly acknowledged the weight of this problem. In contemplating it, he sensed that freedom wasn't about choosing to become some pinnacle of achievement. In his famous commencement speech at Kenyon College a few years before his death, Wallace said that the problem with freedom as defined by our world is that it "has harnessed these forces in ways that have yielded extraordinary wealth and comfort and personal freedom. The freedom all to be lords of our tiny skull-sized kingdoms, alone at the center of all creation." In Wallace's eyes, the American experiment had conflated absolute freedom with absolute solipsism.

Wallace pointed out what lies beneath the problem for Gatsby and Draper: "Worship power," he said, "and you will end up feeling weak and afraid, and you will need ever more power over others to numb you to your own fear. Worship your intellect, being seen as smart, you will end up feeling stupid, a fraud, always on the verge of being found out." Real freedom, in Wallace's estimation, "involves attention and awareness and discipline, and being able to truly care about other people and to sacrifice for them over and over in myriad petty, unsexy ways every day."

Freedom, contra Sartre, is about obligating yourself to others—not freeing yourself from their expectations. It is about finding yourself in the steady, unrelenting, knowing, freeing gaze of someone who knows you—you, the you that you despise—and who is glad to be near you, who loves you anyways. Freedom, at its core, is about love, is inextricable from love, is love.

"Perfect love," John reminds us, "casts out fear."

Gatsby doesn't worship Daisy, despite his (and maybe Luhrmann's) protestations to the contrary: He worships Jay Gatsby. Draper worships only Don Draper. We love who and what we worship. But Gatsby doesn't ever get to discover that thing, the sole salvific thing for which we might hold out for Don Draper: True freedom lies in love, and attention, and sacrifice for others—and in leaving the door open for others to do the same for us.

The Gospel of Gatsby and Draper

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Leonardo DiCaprio as Jay Gatsby and Carey Mulligan as Daisy Buchanan in The Great Gatsby

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Leonardo DiCaprio as Jay Gatsby in The Great Gatsby

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Jon Hamm as Don Draper in AMC's Mad Men

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Jon Hamm as Don Draper in AMC's Mad Men

The film pioneer Roberto Rossellini (who married Ingrid Bergman and fathered acclaimed actress Isabella Rossellini) thought there was something more important about his films than their new, experimental style. In a 1954 interview with Maurice Scherer and Francois Truffaut in the influential Cahiers du Cinema, Rossellini insisted that what made his films distinctive had less to do with his cinema style than with his approach to his subject matter. "For me," he said, "it is above all a moral standpoint from which to view the world. Afterwards it becomes an aesthetic standpoint, but the point of departure is definitely moral."

It's now 35 years after Rossellini's death, and closing in on the seventieth anniversary of the post-war trilogy (Rome Open City; Paisan; Germany, Year Zero) that cemented his reputation. And his films are more important than ever. They're a stark contrast with our own cultural landscape. Today, spectacle is king and filmmakers need celebrities to ensure box-office payoffs for their franchises. But Rossellini reminds us that film can challenge our assumptions and make us wrestle with moral questions.

Rossellini is one of the pioneers of the Italian neorealism movement in film. Stylistically, "neorealism" usually refers to shooting on location, using non-professional actors, and – importantly – not relying on what Scherer and Truffaut refer to in their interview as "cinematic effects." This isn't just the absence of special effects; it's a kind of impassive tone. They say of Rossellini's films that they "don't give special emphasis to important moments" and that they "place everything on the same level of intensity." That means they don't depend on the kind of filmic cues that dramatically underline a scene's significance for the audience.

While this is all true, a careful viewing of Rome, Open City makes it clear that Rossellini was right when he said his primary concerns in his early films were moral, not aesthetic. He helped invent a new style – a new film language – in order to tell particular (moral) stories more effectively, not just because he wanted to do something new.

The title of Rome, Open City, his first international success, refers to the Italian capital's status as neither liberated nor actively defended at the end of World War II. By showing a city demoralized by war, now living in the shadow of imminent but still unrealized deliverance, Rossellini makes a strong metaphor for the Christian spiritual condition.

The plot is loosely structured around an Italian resistance fighter's attempts to avoid being captured by the Germans. But the first half of the film is as much about setting as it is about advancing the plot. Daily uncertainties wear on the people and make the idealistic compromisers hard to distinguish from the scheming opportunists. When a crowd breaks into a bakery during a bread riot, a sexton crosses himself and then joins the fray. A German officer looking out a basement window for a fugitive pauses to glimpse up the skirts of women walking above him.

The people are not particularly depraved—that will come in the second act's torture scenes. They are just bent to the harsh realities of a world where hard daily compunctions overshadow all other concerns. "There are things you do without thinking," one resident confesses "that don't feel like you are wrong."

In another sobering exchange, two women walk through the crumbling city. "Do you think these Americans really exist?" one asks. Glancing at the shells of some bombed-out buildings, her companion shrugs indifferently and says only "It appears so." The occupants of Rome feel as though they are victims of forces beyond their control. They are ruled by great powers far removed from their daily lives.

In that sort of world, you can easily assume your moral choices are inconsequential. Or, at least, it is easier to soothe and rationalize away your moral reservations. But that lasts only until a moral torpor blurs the lines between victims and victimizers to the point of spiritual confusion.

As the film moves to the second act, the action begins to condense around the interrogation of a resistance fighter. Don Pietro (not the same figure who participated in the bread riot) emerges as a central figure. He is the conscience of the film. His is not a removed, impartial faith. He helps the resistance hide guns and uses his relative freedom from curfews to deliver messages to the underground.

But neither is Don Pietro a revolutionary in priest's garb. After being forced to witness the prolonged torture of a suspected insurgent, Don Pietro curses the Germans and then stops, horrified at what he has done: "My God, what have I said? Forgive me Lord." It is Don Pietro who will eventually deliver the film's thematic coda when he says that "it's not that hard to die a good death," and then continues, "what's hard is to live a good life."

This mentality – as horrified by its own anger and cursing as by the oppressor's tyranny – may seem foreign to a modern audience. After all, we are steeped in revenge narratives and the rhetoric of cultural and political self-righteousness. Perhaps the greatest accomplishment of the film is that it makes Don Pietro's self-approbation appear natural, human, and normal. He is not an exceptional Christian; he is a normal Christian in exceptional circumstance.

This theme is developed subtly. Rossellini always frames his characters' struggles within a long historical perspective. The film's final shot juxtaposes children and the Roman skyline with St. Peter's dome featured prominently. This reminds us that as topical as the film was and as fresh as the psychic wounds from the war were (it was released less than a year after VE day), they were not unique in the world's history. Rome was an open city centuries before. Each generation must wrestle to live a good life regardless of the proximity of death. Rossellini also links the modern with the ancient in his masterpiece Journey to Italy (Viaggio in Italia), where the estrangement of an English married couple (Ingrid Bergman and George Sanders) plays out against the backdrop of a tour of the ruins of Pompeii.

In a sort of paradox, the sweeping historical perspective of Rossellini's films highlights rather than diminishes their moral questions. They force us to look beyond the scope of one life or one generation. And in so doing, they invite an analysis that is broader than what most current movie narratives provide.

You can find a striking contrast to Rome, Open City in Kathryn Bigelow's Zero Dark Thirty, which compresses over a decade of action into a single narrative. By doing so, it reduces the breadth of its moral questions (such as the use of torture) from the broadly philosophical or moral ("is it right?") to the narratively pragmatic ("did it work?"). Ben Affleck's Argo uses history as merely a backdrop, with the roots of the Iranian revolution covered in a two minute prologue and the coming years of war between Iran and Iraq elided as champagne is served on the plane, accompanied by retrospective pats on the back. But the inability to consider moral questions that stem beyond "the mission" is not unique to Argo – just most pronounced in it.

Oddly enough, the one recent popular franchise that gets close to Rossellini in this way is George R. R. Martin's A Song of Fire and Ice. By spanning multiple generations and using multiple points of view, that series of novels (and the HBO series Game of Thrones, which is based upon it) invites readers (or viewers) to judge its characters' actions by more than whether or not they are effective. But not surprisingly, as the novels and series have progressed, the lack of a moral center embodied in a single, central protagonist has brought on some negative critiques, just as Rome, Open City initially underwhelmed an Italian population weary with the moral demands of war and seeking escapism in its movies.

It is hard to imagine seeing a corollary character to Don Pietro in Zero Dark Thirty, someone who would look at terrorism and torture and be repulsed by his or her own drive for vengeance. In the world depicted by that film, history extends only as far back as 9/11. The traumatic years of war in Rome, Open City are placed in a broader, cosmic historical span that helps guard against our tendency to see our own moment in history as exceptional.

After Rome, Open City, Roberto Rossellini would work regularly for over three decades until his death in 1977. His style would develop beyond neorealism—he told Cahiers that "one can't forever shoot films in bombed cities"—but he never deviated from his focus on people as moral creatures confronted with the challenge of how hard it is to "live a good life." He would go on to film Federico Fellini's screenplay for The Flowers of St. Francis, film Ingrid Bergman in Giovanna d'Arco al rogo (Joan at the Stake), write a television miniseries on the Acts of the Apostle and direct television films on Augustine of Hippo, Socrates, and Blaise Pascal.

Linking his portraits of everyday people with historical saints was the belief that the latter were no different in essence from the former: "[…] It seems to me that what is so astonishing, so extraordinary, so moving in human reality is precisely the fact that noble acts and momentous events happen in the same way and produce the same impression as the ordinary facts of life; I therefore attempt to convey both in the same manner—a method with its own very definite form of dramatic interest…"

Rome, Open City will play on Turner Classic Movies on May 15, at 12:00 a.m.