The Heirs to Holden Caulfield

Novelist Nathaniel Rich mourns the loss of a literary hero—and fantasizes about the books that Salinger was possibly writing all of these years.

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The unnamed narrator (Bright Lights, Big City)

It’s easy to imagine the anonymous narrator of Jay McInerney’s 1984 novel Bright Lights, Big City as a modern-day Holden Caulfield—if say, Holden had a serious addiction to Bolivian Marching Powder. McInerney’s rare second-person story takes us through the lonely days and yuppie-filled nights of a would-be writer/magazine fact checker (played in the movie version by Michael J. Fox) immersed in the Manhattan party scene of the 1980s. McInerney’s secondary characters also feel like the same phonies Caulfield railed against. And like in Salinger’s classic work, McInerney offers detailed portrayals of New York itself, allowing it to become a prominent character. In both books, the city is pitted against a protagonist depressed by personal catastrophes and bored by what life has to offer. You know who you are.

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Max Fischer (Rushmore)

While Holden Caulfield was introduced to readers upon his expulsion from Pencey Prep, 15-year-old Rushmore Academy student Max Fischer was all about school—just not the academic portions. In 1998’s Rushmore, Fischer, played by Jason Schwartzman, is the most extracurricular and least scholarly young mind walking the institution’s prestigious halls. Unlike his silver spoon-fed classmates (and Caulfield), Rushmore’s not-so-star student attends the elitist institution on scholarship. But Fischer’s attempt to break ground on an aquarium sans school approval leaves him in Caulfield’s shoes—expelled. Without Rushmore, his self-proclaimed lifelong love, the once-cocky Fischer increasingly fades into the state of Salinger’s beloved manic-depressive. Despite similar schooling and un-schooling and peculiar relationships with older women, the two teenage boys still stand apart on certain issues—a maroon beret is one of them.

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Jim Stark (Rebel without a Cause)

The title of the iconic 1955 film could easily work on Salinger’s acclaimed novel. Both center on young men teetering on the edge of destruction. Trade the prep school garb for a leather jacket and some hair gel, New York for Los Angeles, and city eccentricities for urban violence, and James Dean’s Jim Stark could be Holden Caulfield. Their melodrama also seems similar—Stark’s line, “I don’t know what to do anymore. Except maybe die,” could come from Caulfield on a darker day. But by their respective stories’ ends, Stark seems to have grown from his personal tragedies while Holden remains stagnant in the depressive state of his upper middle class oppression. Poor little rich boy.

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Igby Slocum (Igby Goes Down)

Flash-forward The Catcher in the Rye 50 years and you have the scene of 2002’s Igby Goes Down. Stifled by his tightly wound, financially fortunate family, 17-year-old misanthrope Jason “Igby” Slocumb begins to unravel. The comparisons are inevitable—Igby, played by Kieran Culkin, loathes his fascist older brother Ollie (a la Caulfield’s D.B.), flunks out of multiple prep schools, and attempts to find better on the island of Manhattan he grew up on. But unlike Caulfield, Igby has the benefit of barbiturates, marijuana, and the occasional roll in the sheets to deal with his less affable name for the degenerates that surround him. Holden railed against phonies, while Igby says bluntly, “I’m drowning in assholes.”

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Gene Forrester (A Separate Peace)

Holden tries desperately to stop the inevitable process of growing up to “catch” those he loves before they fall from grace. Images of literal falls—from children running off a cliff to a boy jumping to his death from a window—fill the novel. “I was sort of afraid she’d fall off the goddam horse,” he says as he watches his little sister ride on a carousel. The teenage narrator in John Knowles' classic A Separate Peace, published eight years after The Catcher in the Rye and also set against the backdrop of prep school, experiences similar anxieties about the loss of innocence. And he sounds a lot like Holden, too. “That goddam tree, I'm going to cut down that tree,” Gene Forrester says after his closest friend tumbles off a branch and shatters his leg. “...How did you fall, how could you fall like that?” The same friend later falls down a flight of marble stairs and dies in the school infirmary soon after, leaving Gene to face adulthood alone.

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Jess Mariano (Gilmore Girls)

If teen angst had a face in the 2000s, it would be the short, dark, and handsome visage of Jess Mariano, Rory Gilmore’s tortured on-again-off-again boyfriend on Gilmore Girls. The television drama is ridden with quips and pop culture references, and Salinger does not go unnoticed. Far from the bright lights of New York and instead suffering in the sleepiness of the fictional Stars Hollow, Connecticut, Jess (played by Milo Ventimiglia) embodies the cynicism of adolescence that Caulfield introduced audiences to a half-century earlier. Jess is intellectually inclined, but a rebel who resents authority and challenges it at any and all costs. “All you do is make life harder,” Rory tells Jess, who eventually leaves her for New York. “I guess that’s what you have to do when you’re trying to be Holden Caulfield.”

Lee Fiora (Prep)

If the unlovable, enormously self-conscious narrator of Curtis Sittenfeld’s 2005 debut novel Prep was bold enough to join Match.com, she may have found her man counterpart in someone like Holden Caulfield. After leaving the serenity of her Indiana hometown for a scholarship to attend Ault, a prep school outside Boston, 14-year-old Lee finds herself immersed in a WASPy world. Like Holden and his cynical successors, she doesn’t embrace the superficial students who surround her, who share names with characters on Gossip Girl and jump up and down at pep rallies, exuding glee most awkward teenagers rarely feel.

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Benjamin Braddock (The Graduate)

While one contemplated a career in plastics the other sought to escape the artificiality of his upbringing, but nevertheless, the parallels between The Graduate’s Benjamin Braddock and Catcher’s Caulfield are inescapable. No fake tears have fallen for the prototypical antiheroes of the ‘50s and ‘60s, who both face a crossroads in their stories—one recently completing school and the other given the boot. But they’re plagued by their privileged upbringing, and their mutual dissatisfaction with life’s gold-plated offerings leave them wanting to make their own place in the world. While Benjamin wrestles with more romantic issues than Holden, they’re equals economically and woefully. “Goddam money,” says Salinger’s director of despondence. “It always ends up making you blue as hell.”

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Holden Worther (The Good Girl)

Jake Gyllenhaal has made a career out of playing angst-ridden characters that resemble Holden Caulfield, but never more so than in 2002’s The Good Girl. His character Tom Worther is such an avid fan of The Catcher in the Rye that he insists on going by the name Holden. But instead of being tormented by a city, Gyllenhaal’s Holden is numbed by his day-to-day life in a slow suburb, where he works in a drugstore alongside similarly frustrated characters played by Jennifer Aniston and Zooey Deschanel. The setting may be different, but the alienation and malaise are the same. “You know, sometimes I think to myself: At least it can’t get any worse. But it can,” Worther says at one point. “As long as you can say you hit rock bottom, you haven’t.” He’s so tormented, in fact, that Worther ends his own life, a fate more severe, but eerily similar to Caulfield’s eventual institutionalization.

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Clay (Less Than Zero)

Upon returning home to Los Angeles for the holidays during his freshman year of college in New Hampshire, Clay, the rich, disaffected protagonist of Bret Easton Ellis’ debut novel Less Than Zero comes to learn his girlfriend has been sleeping with his increasingly drug-addicted high school friend. As supersaturated children of Hollywood moguls in the ‘80s, Clay’s clique is mostly directionless or headed downward. It’s the unglamorous life of those who believe they are the epitome of glamour, but Clay (played in the film version by Andrew McCarthy) knows better. Still, there’s not much “anti” in the tragic hero that he turns out to be. In the end, all he wants is a girl in his bed and his MTV. As for Ellis, while his novel no doubt owes a debt to Salinger, he was not exactly sentimental upon learning of his passing. “Yeah!! Thank God he's finally dead,” he charmingly Tweeted. “I've been waiting for this day for-fucking-ever. Party tonight!!!”

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Travis Bickle (Taxi Driver)

Though the innocence is lost, a clear strain of Salinger’s antihero has long been documented in Travis Bickle, the even more bitter star of the 1976 Martin Scorsese classic Taxi Driver. With their shared sexual encounters of the emotionless kind and mutual misery with life in Manhattan, Bickle (played by Robert DeNiro) and Caulfield are kindred woeful spirits. Without the self-awareness and self-deprecating sense of humor that make even the privileged Caulfield so relatable, Bickle is just plain sad—and dangerous. Equally serious is another legendary connection between Taxi Driver and The Catcher in the Rye: John Hinckley Jr., who attempted to assassinate former President Ronald Reagan in 1981, was a fan of both.

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Angela Chase (My So-Called Life)

With her flannel-filled wardrobe and dark red dye job, My So Called Life’s heroine Angela Chase was the 1990s answer to Holden Caulfield, and a role model for disaffected teenage girls everywhere. The 15-year-old, played by Claire Danes, embodied the spirit of suburban teen frustration. As Angela dealt with the pressures of clueless parents, unrealistic teachers, and the social minefield that is freshman year of high school, she narrated her experiences to the viewer in the same candid manner Caulfield uses. “My parents keep asking how school was,” Angela recalls in one episode. “It’s like saying, ‘How was that drive-by shooting?’ You don’t care how it was; you’re lucky to get out alive.” With his readers proving yet again that when it comes to life as a teenager, some things never change.

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Todd Anderson (Dead Poets’ Society)

At Vermont’s all-boys Welton Academy, it was a teacher who showed his students to break away from the conformity of their conservative aristocratic environment in the 1989 film Dead Poets Society. One such pupil, the perpetually nervous Todd Anderson (Ethan Hawke) eventually breaks through his shy exterior, channeling the creativeness he finds he possesses with the help of his English teacher John Keating (Robin Williams). From his adolescent alienation, Anderson eventually loses his innocence, akin to Salinger’s most celebrated character in shouting, “O Captain! My Captain!” in support of his fallen professor amid scandal. In his unintentional, but shrewd way, Anderson enlightens those around him. “Truth is like a blanket that always leaves your feet cold,” he says in the film. “You push it, stretch it, it’ll never be enough. You kick at it, beat it, it’ll never cover any of us. From the moment we enter crying to the moment we leave dying, it’ll just cover your face as you wail and cry and scream.” Holden Caulfield would have understood.