By the time he was thirty-eight years old in 2000, Kenneth Lonergan was already an established playwright with enough New York productions and award nominations on his resume to constitute a distinguished career for a man two decades his senior. He had also already dipped his toe into the more financially lucrative world of Hollywood by selling his spec script for the mob comedy Analyze This (1999) that eventually starred Billy Crystal and Robert De Niro. Then Lonergan wrote and directed You Can Count on Me (2000), a film that was both a commercial success and a critical smash. You Can Count on Me won the Grand Jury Prize at Sundance, along with a score of other awards and landed Oscar nominations for star Laura Linney and for Lonergan’s screenplay. Those of us who love movies in general, and You Can Count on Me in particular, couldn’t wait to see what Lonergan did next. Two years later, he landed another screenwriting Oscar nomination for Martin Scorsese’s Gangs of New York (2002), and he returned to the New York stage with so much success that he was hailed in certain quarters as the nation’s most important playwright of the last two decades.

But where was that next movie, not for hire, but for himself? Where was the follow up to You Can Count on Me? The answer: in Hollywood hell. Shortly after finishing his work on Gangs of New York, Lonergan undertook the writing of the film that would be released a long time later as Margaret (2011). His reputation was such that he attracted A-list filmmakers Sydney Pollack and Scott Rudin as his producers and was granted the special privilege of authority over the “final cut,” as long as he delivered an edited film of no longer than 150 minutes. That length restriction eventually became a stumbling block of Himalayan proportions.

Lonergan worked on the Margaret script for two years, revisiting many of the themes he had first raised in You Can Count on Me. But when he began shooting in the summer of 2005, he had a screenplay for a three-hour film that he hoped he could reduce to the required 150 minutes in the editing suite. This proved to be a horrible miscalculation. Despite two years of post-production efforts, Lonergan just wasn’t able to cut the material to contracted length. The result was several lawsuits by investors that further held up the film’s release. Lonergan ended up having to borrow several hundred thousand dollars from his friend and collaborator Matthew Broderick. His mentor, Scorsese, was eventually brought in to produce a 160-minute cut, an undertaking of loyalty and friendship that came to naught when investors rejected Scorsese’s efforts, some have said just to punish Lonergan. Sufficient compromises were finally achieved, and Margaret was released in September 2011, if you can call being shown in one theater in New York and one in Los Angeles as “being released.” It returned a gross box office of $46,495 on an initial investment (not including Broderick’s thousands) of $12.5 million. In practical terms, no one saw the movie. Nonetheless, critics have called it a “masterpiece.” The New Yorker termed the film “a cinematic wonder.”

From the very outset of Margaret, Kenneth Lonergan probably attempted the impossible. Our public cinemas are now the homes of special effects extravaganzas, the purview of super heroes in the land of fantasy and science fiction. And though that trend was already underway when You Can Count on Me was released in 2000, it is so far advanced today that enticing an audience to sit still for over two and a half hours for a drama about a self-centered high school junior, seems a fantasy of a different kind and order. Whatever its considerable artistic ambitions and merits, as an act of commerce Margaret was probably dead on arrival from the moment it was conceived. That’s the bad news—for Kenneth Lonergan, all his supporters, and cinephiles of a certain kind, like me. The good news is that Margaret is now available on DVD and can be appreciated on the home flat screen the way we appreciate such superior television fare as The Wire, Treme, Mad Men, and Homeland.

Kenneth Lonergan’s storytelling is rich and challenging because he refuses to see human beings in black and white. His scripts continually shift the angle from which he examines his characters, and thus we see them in an unusual wholeness, their blemishes as well as their beauty. In You Can Count on Me, Samantha Prescott (Linney) would seem the epitome of small-town propriety. She is the chief loan officer at the Scottsville bank in upstate New York. She owns her own home. And she provides the energetic kind of loving concern for her eight-year-old son Rudy (Rory Culkin) that has turned the nation’s so-called “soccer moms” into a potent political force. But maybe Samantha is not quite the rock of stability and good sense she seems. And perhaps some of the other folks we meet in this film are not quite what they seem either.

The story in You Can Count on Me largely concerns Samantha’s relationship with her brother Terry (Mark Ruffalo). Samantha and Terry were orphaned as young children when their parents were killed in an auto accident. We do not know exactly how they grew up, whether they were placed with relatives, in a foster home, or in an orphanage. We do know, however, that even as adults in their late twenties or so, they remain fiercely, if imperfectly, connected to each other; their bond, no doubt in significant part, forged from their shared suffering. That Samantha fiercely cherishes her brother cannot be doubted. When she gets the letter announcing that he is coming for a visit, her face lights up with a rapturous glow, and on the day of his arrival, she dresses up as if she’s going on a date. But how outwardly different these siblings have become. Samantha is resolutely middle class and responsible. She earns a good income, and she lives modestly well. Terry, in contrast, is a mess. He is an itinerant laborer with undefined skills in the building trades. He would appear to know a little carpentry and perhaps some plumbing, but he has certainly never settled down. Thoroughly alienated from the small-town atmosphere in Scottsville where he and his sister were born and where Samantha still lives, Terry moves from place to place, never settling for long anywhere. Perhaps foremost among her concerns about Terry, Samantha worries constantly about his whereabouts. He has been in Florida, and he has been in Alaska, and, more problematic, he has been in jail.

We have lots of reasons for questioning Terry’s judgment. When we first meet him, he is taking his uncomfortable departure from a troubled young woman named Sheila (Gaby Hoffmann). Sheila is pregnant with Terry’s child, and neither of them possesses the money for an abortion. More painfully, Sheila appears far more attached to Terry than he to her. Terry seems to have no desire to hurt Sheila, but on the other hand he apparently lacks the good sense to avoid getting seriously involved with someone he does not love. Terry visits Samantha for the express purpose of borrowing enough money to fund Sheila’s ­abortion. In a host of other ways, Terry continues to exhibit throughout the picture a core quality of habitually poor decision making. While staying with Sheila, he forgets to fetch Rudy from school as requested and leaves the child out in the rain. On another occasion, Terry takes Rudy to a bar instead of putting him to bed. And at his most irresponsible, Terry takes his nephew to see the boy’s father (Josh Lucas), a scruffy lout who denies his paternity to Rudy’s face.

Just as we begin to determine that You Can Count on Me is a story of diametrical personalities, however, we begin to spy the cracks in Samantha’s facade of respectability. In a metaphor for her darker nature, when authorities show up to tell a thirteen-year-old Samantha about her parents’ accident, the kids for whom she is ­babysitting decide that she has sneaked outside for a smoke. Nonetheless, we are stumped by her later teenaged involvement with a man like Rudy Sr. The answer perhaps lies in Terry’s oblique reference to Samantha’s “wild side.” After a time, we conclude that by “wild,” Terry probably means “ill-considered.” Nine years ago, surrendering to an attraction that must surely have been fleeting, Samantha allowed herself to become pregnant by Rudy Sr. Today, Samantha goes to dinner with an old beau (Jon Tenney) she has not dated in over a year and nonetheless ends up in the man’s bed before the end of the evening. And then, in an almost inexplicable fit of carnal surrender, she plunges into a clandestine affair with her boss Brian Everett (Matthew Broderick), a man she does not even like and one who does not even pretend he might leave his pregnant wife Nancy (Nina Garbiras). Samantha isn’t even entirely faithful to the person she believes she loves unconditionally: Terry. Samantha does care deeply about Terry, but her concern often ­manifests itself in irritation and scolding tirades. It’s no wonder that he’s so morose around her.

In short, Samantha is neither as responsible nor as reputable as we initially presume, and certainly not as wise (Lonergan cleverly manipulates our class prejudice for his own thematic ends). She justifies running personal errands on company time because they inevitably involve child care issues. She fails to keep her employers properly notified when she has a family crisis. And in so doing she exhibits far more in common with Terry than she would ever admit. In the film’s most artfully subtle moment, Samantha coolly threatens Brian with a sexual-discrimination lawsuit and flirts with the idea of corporate insurrection. At the same time, Terry is not quite the uncaring leech we at first judge him. His actions are often unwise, and he is completely, unreconstructably undisciplined. But his heart is often in the right place. He does care for his young nephew. Terry tries to teach Rudy about carpentry, and he manipulates a barroom pool game so that Rudy can sink the winning ball, much to the child’s pride and pleasure. Terry also genuinely cares for his sister. He tells Rudy that the boy’s greatest luck is the goodness of his mother. Terry even cares for Sheila in a way that wins him at least partial redemption.

A significant theme in You Can Count on Me, as in Margaret, is the extent to which adults continue to act like children. We even have a scene in which, like a child, Terry plays intently with Rudy’s Gameboy. Terry engages in a snit about tattling with Rudy that recalls the argument of youngsters in a schoolyard. Samantha’s sexual promiscuity, and Terry’s as well, is like that of adolescence. Consequences don’t enter their consideration. Samantha’s trysts with her boss Brian initially even take place in his car, just like teenagers on a back-road lovers’ lane.

Lonergan refuses to place blame on the usual suspects. The people of Scottsville are not the monsters and perverts who stand in every small-town storefront created by someone like David Lynch. The local sheriff (Adam LeFevre) is a man of patience and concern. The local pastor (Lonergan) is a man of considerable compassion and reluctance to judge. In the end, Lonergan avers the role of fate in our lives. The trajectories of Samantha’s and Terry’s lives were no doubt unalterably changed by the deaths of their parents. Today, they have the virtue of genuinely loving each other, but neither can change the nature of the other. As a result, they will continue to disappoint each other for some time to come, maybe forever. And that is the downbeat message in this film’s almost shockingly quiet conclusion. On the other hand, in the magic of a thematic paradox, their love endures. Terry goes away again, but promises to stay in touch, promises to return. And maybe he will. And born of love, maybe he and his sister will finally find a way to fulfill each other as both of them do so desperately desire.

Samantha and Terry Presscott obviously stand for many of us as we try to wend our way from youth to adulthood, but the canvas of You Can Count on Me is small, a brother and a sister in a small town. Margaret is more ambitious and explores more and broader themes, not in a rural, isolated village but in New York, one of the world’s busiest and most crowded cities. Lonergan likes to establish visual metaphors from the physical landscape surrounding his characters. In You Can Count on Me, the director’s camera notices a graveyard as Terry’s bus takes him to visit his sister, establishing that the bond that connects them was forged by their parents’ accidental deaths. And though we can extrapolate lessons for ourselves from the lives of Samantha and Terry, Lonergan urges that kind of connection explicitly in Margaret with his repeated shots of New York cityscapes: the crush of pedestrians on daytime sidewalks, the endless lights of countless high-rises gleaming through the night, the inevitable clot of traffic stretching to the urban horizon. The characters he deals with in Margaret are instructive, but representative. There is a narrative for everyone we pass on a crowded street, for everyone tapping fingers in a car waiting for the light to change, for everyone in every office and apartment from which silver light spills into the night-darkened sky.

Like You Can Count on Me, the story in Margaret is propelled by an accident. High-school junior, Lisa Cohen (Anna Paquin) runs along a daytime Manhattan street, flirting with bus driver Gerald Maretti (Mark Ruffalo) at the wheel of his Transit Authority bus. Distracted, Gerald runs a red light and drives over middle-aged pedestrian Monica Patterson (Allison Janney), tearing her body to pieces and leaving her only minutes to live. Lisa doesn’t know Monica, but she rushes to hold her while they wait for an ambulance that arrives only after Monica has bled to death in Lisa’s arms. When the police arrive, Gerald and Lisa exchange furtive glances and then tell the same story: the bus went through the intersection on green; Monica walked against the light.

But, her conscience stricken, Lisa first tells the true story to her mother, Broadway actress, Joan Cohen (J. Smith Cameron), who observes that perhaps Lisa should think of the bus driver and his family before returning to the police to correct her story. Monica’s death was still an accident, and acknowledging that the driver was distracted will not bring the victim back to life. Particularly in retrospect, this is good advice. But Lisa refuses to take it. She changes her police report, but the police say that even if Gerald was distracted as a result of her flirting, Monica’s death was still an accident and no grounds exist for charges. Enraged, Lisa makes contact first with Monica’s cousin Abigail (Betsy Aidem) and subsequently Monica’s best friend Emily (Jeannie Berlin). In the latter, Lisa finds a kindred angry soul, and together Emily and Lisa devise a plan to bring a wrongful death suit against Gerald, a court action they hope will get him fired. Complications ensue. Emily and Lisa have no standing to sue, so they do so in Abigail’s name. But once Abigail is involved, it is clear that she will gladly take whatever money can be extracted but cares little about anything else in the matter. She and Monica weren’t even on friendly terms. And, of course, Gerald hasn’t any money, so the suit ends up against his employer, the Transit Authority. One wouldn’t expect much good to come out of any of this, and none does.

Along the way, however, we are confronted with a series of characters, very few of whom elicit much in the way of our sympathy. Lisa’s divorced father Karl (Lonergan) lives in California and stays in occasional contact with his daughter by telephone, but his self-absorption is so noxious we can almost smell it. When Lisa tells him about her bad conscience, his first reaction is to invoke the advice of a lawyer to protect Lisa and himself from a prospective, and never threatened, lawsuit. Joan is somewhat better. We do believe that her caring for her daughter is real, but Joan is also so self-absorbed that when she meets Emily, rather than talking about Monica, Joan rambles on about her own career and how nice it is to enjoy the occasional success and attract critical praise in the reviews. Emily is an emotional monster. Her grief has turned into such fury that she simply wants to hurt someone. She isn’t ever particularly nice to Lisa, even though Lisa provides her the weapon with which to wield her anger. She is flat and pointlessly rude to Dave (Michael Ealy), the lawyer friend who tries to help her. She creates a horrible public scene when confronted with an insensitive remark by Joan’s boyfriend Ramon (Jean Reno). And ultimately Emily turns her wrath on Lisa, accusing the teenager of “caring too ­easily,” and upbraiding Lisa that “You’re not the one this is happening to.” That we agree with both of these observations in no way lessens the cruelty with which they are delivered.

But if an array of the characters are unsympathetic, Lisa stands foremost among them. She is a bright girl, and, except in math, a good student. But she is also frighteningly immature and needlessly mean. She bullies her younger brother, simply because he is too little to stop her. When Darren (John Gallagher), the socially shy boy who tutors her in math, asks her to the movies, like a cat toying with a trapped mouse, she tries to tie him in knots over whether the invitation is a “date.” She relates to her imperfect mother with a series of sneers, sarcastic remarks, and outbursts, and when her mother stands up to her, she threatens to move to California to live with her father. When Lisa is with the police, she is needlessly combative even before she is denied her desire that Gerald be arrested, and afterward she accuses the detectives, outside of all context, of being racists. Outside of school, to his face, she ridicules her English teacher (Broderick), even though he is trying to look out for her, and she snidely asks her math teacher, Mr. Aaron (Matt Damon), if being a high-school geometry teacher is “the summit of his ambition.” When Mr. Aaron is uncomfortable around her, she sniffs that he’s “acting just like a little kid.”

Along with an ingrained nastiness, this last jibe is an example of another of Lonergan’s themes: hypocrisy. Lisa repeatedly acts like a spoiled child, yet accuses others of this characteristic. When Emily attacks her, Lisa complains, “I don’t understand why if I do something wrong, you can’t just give me a break.” But, of course, her crusade against Gerald is a prime example of her doing the same thing. Even the few “good” characters suffer from hypocrisy. Joan’s boyfriend Ramon, a Panamanian who has made a fortune in Paris and used his wealth to build orphanages in his home country, is nonetheless capable of dismissing a pro-Israeli argument (he’s pro-Palestinian) as a “typical Jewish response.” He would recoil at being disregarded in that manner but cannot bring himself to understand that he has been offensive.

And as in You Can Count on Me, Lonergan once again has things to say about careless sexual behavior. Joan and Ramon move from mere acquaintances to bedmates perhaps too soon, certainly before Joan is sure that Ramon is the man with whom she wants to spend the rest of her life. But again, Lisa is our chief offender. When we first see her with Mr. Aaron in her math classroom, Lisa is wearing a skirt so short it barely covers her panties, if she’s wearing panties. Yet, as she is discussing his concern that she used unauthorized assistance on a take-home geometry test, she sits in front of him, and akin to Sharon Stone in Basic Instinct, ostentatiously crosses her legs in a way that flashes him. Because Mr. Aaron does not respond, we don’t know if he’s looking at her at that moment or, for certain, even if she has done this on purpose, but in her dress and physical movements she will win no trophies for appropriate modesty. She is a virgin, however, or at least believably claims to be. For after making out with Darren at a party and heartlessly telling him that she loves him, she calls another boy from her school, the drug dealing Paul (Kieran Culkin) and asks him to deflower her. That their night of sex together seems to reveal her almost utter lack of experience and confidence might otherwise elicit our sympathy, had her behavior not already turned us so stubbornly against her. And what sympathy she does command on her night with Paul is soon squandered when she goes to Mr. Aaron’s house and aggressively seduces him. The teacher flunks adulthood for surrender to a teenager, but as Lisa admits, the idea, overture, and determination all came from her.

Also akin to You Can Count on Me, Margaret worries about the stubborn childishness that we cling to. This is related to the theme of self-­absorption discussed above, for any parent knows the ways a child can see things from his or her perspective alone. It is, thus, no accident that two of Joan’s party tricks are to sing in the voice of the four-year-old Shirley Temple and to cry like a baby awakening for a nighttime feeding. Like Samantha in You Can Count on Me, when Joan is frustrated, she is prone to smash things around her house, to sweep a dinner’s worth of plates crashing to the floor. Mr. Aaron is childish in surrendering to his student. Ramon is childish by resorting to contempt rather than rational discussion. Even the English teacher is childish for a moment when he cannot dissuade a student from repeating the same, wrongheaded, extra-textual point in a discussion about Shakespeare. Elsewhere, Lonergan drives home this concern about childishness when he has the English teacher read Gerard Manley Hopkins’s poem, “Spring and Fall, to a Young Child,” in which the poet counsels a girl named Margaret (hence the movie’s title) who is worried about the coming of autumn and ends with the couplet “It is the blight that man was born for/ It is Margaret you mourn for.” In short, ours is a youth-obsessed culture, and we do ourselves no favors by refusing to grow up.

And there is more. Working from a script begun in the months after the attacks on the World Trade Center and the Pentagon, there are heated discussions about Islamic terrorism and the reasons that America is hated by so many in the Muslim world. And lest we forget an underlying cause of all that, in his shots of the physical environment, Lonergan’s camera sometimes spies gigantic oil tankers easing into the ports of New York harbor.

In sum, though I am a fan of Kenneth Lonergan and an admirer of this movie, I can understand why he had such a difficult time producing the final cut that was his obligation and prerogative. First, I think he was too devoted to all those shots of Manhattan streets, buildings, waterways, and anonymous people. They interrupt the action repeatedly to diminishing effect once we realize the point he is making. And, in every case, he lingers on them longer than necessary. They slow things down in a way that doesn’t serve the movie. The more extensive problem, though, stems from Lonergan’s early decision to make so many of his characters so deeply dislikable. Margaret’s lineup of characters includes few saving graces. We may recognize that Emily is suffering over the loss of her dear friend, but she doesn’t have to be so ugly to everyone and so superior in her ugliness to boot. We may realize that Mr. Aaron is the pursued, not the pursuer, but it is his obligation to resist the very kind of temptation he surrenders to. We may realize that Ramon is a decent man, but that is no defense against his anti-Semitism. We may realize that Joan lacks self-confidence and is involved in a career that fans the flames of her insecurity, but that doesn’t excuse her lack of maternal strength. We may recognize that Gerald’s momentary irresponsibility merits forgiveness, but that doesn’t forgive his lying, his refusal to accept responsibility, and his knee-jerk hostility toward Lisa. And we may recognize that Lisa’s instinctual effort to comfort the dying Monica and her subsequent pangs of conscience about her role in the accident may indicate that someday she may indeed grow up, but until the very closing scene we see no solid evidence that Lisa has honored her pledge not to turn Monica’s horrible, tragic death into her “own personal moral gymnasium.” I can’t help but wonder if Lonergan didn’t stymie himself in his desire to save characters that his audience would find so distasteful.

Still, there is not a sliver of doubt that save them he intended. And that is why we get the film’s closing scene, mother and daughter, emotionally broken, holding on to each other for dear life. In the complex structure of Margaret’s story, brilliance lies; in its insistent conclusion, wisdom blooms. That we will sin is a given of our human nature. That we can be redeemed is the grace offered by the divine and the possibility that we must all extend to one another.

Fredrick Barton directs the Creative Writing Workshop at the University of New Orleans, where he previously served as Dean of Liberal Arts and Provost. His collection of essays Rowing to Sweden includes many pieces first published in The Cresset. His novels include The El Cholo Feeling Passes, Courting Pandemonium, Black and White on the Rocks, and A House Divided. He served as film critic for the New Orleans weekly Gambit from 1980–2008 and has written for The Cresset on cinema and other topics since 1981.