Holden Caulfield and New York: Academic Essay

Sanaa Sharma
10 min readDec 10, 2020


“I mean, you’re like New York. You’re just this person. You’re like this island unto yourself.”

(Annie Hall, Dir. Woody Allen, Perf. Diane Keaton and Woody Allen, United Artists, 1977. Film.)

The Catcher in the Rye by J.D Salinger describes troubled 16-year old Holden Caulfield’s three-day excursion of New York. Throughout the course of the novel, Holden tends to criticise everything about the city, notoriously labelling everything as phony. However, he moves around New York with a familiarity that suggests the city is his home away from home as it becomes a haven for him to not engage with his parents. While Holden is in New York, he becomes one of New York — an always moving, chaotic amorphous entity. This essay aims to prove that Holden Caulfield’s relationship with New York represents his relationship with himself — an ambivalent, love-hate relationship. It’s one that he finds solace in, yet gets frustrates by at the same time. Throughout the course of this essay, I will first be proving separately that Holden has a love-hate relationship with himself and with New York, and then proving that his perception of New York is synonymous with the change in his perception of himself, tracing his view of New York throughout the novel, as well as the fluctuations in his perception of himself that changes his relationship with the city.

Holden does have a fairly ambiguous relationship with himself that frequents the two ends of the spectrum — love and hate. Both these feelings vary in their intensity throughout the course of the novel. Indications of his relationship with himself are only subtle — his narration only describes the events that took place during his excursion. However, one can garner what Holden thinks of himself from his stream of consciousness narrative. He is quick to criticise everyone and everything around him, especially in New York, where phoniness presents itself on a silver platter at every turn of a street. “It is the world around Holden Caulfield that is negative. It is the world around him that writes dirty words on the walls, does crude things that make the sensitive cringe, that is immoral and duplicitous and vengeful. He is a knight-errant trying to make some sense, find some meaning, gain some understanding.” (Moore, R. (1965). The World of Holden. The English Journal,54(3), 159–165. doi:10.2307/811333). Holden tends to put himself on a moral pedestal of sorts when he points out societal flaws — giving rise to his analogy of The Catcher in the Rye — he is the only adult allowed to be in his conceived world of children. “While Holden is quick to pass sever judgements on others he is not so quick to see the faults in himself”. (Seng, P. (1961). The Fallen Idol: The Immature World of Holden Caulfield. College English, 23(3), 203–209. doi:10.2307/373007) To him, People are the problem. “People never notice anything”, “People never give your message”, “People always think something’s all true”, he laments throughout the novel. “This is a people shooting hat”, he says to Ackley while still at Pencey — he views himself as superior as having been able to have made these observations. He expends his energy denigrating a world he thinks is only deserving of contempt.

However, at the end of the day, Holden is an insecure teenager in a world where he’s so “lonesome” he’s desperate to fit in. The Catcher in the Rye is essentially a series of meaningless interactions where Holden tries to find some purpose and companionship. He frequently criticises himself as he appears frustrated at his inability to form concrete relationships. As his mental health deteriorates throughout the novel, his frustration becomes more apparent. “I’m the most terrific liar you saw in your life. It’s awful”, he says after convincing Ernest Morrow’s mother that he was a man called Rudolph Schmidt. He also seems to be incredibly insecure about his intelligence, commenting on how he’s “illiterate but reads a lot”. He also becomes visibly uncomfortable when Mr. Spencer starts reading out his mediocre essay to him. “Don’t tell her I got kicked out, will ya?”, he asks of Stradlater when he’s going on his date with Jane Gallagher, an old-time friend of his. Holden can’t seem to stand that he’s been expelled from Pencey that he escapes to New York in a search for some semblance of comfort and meaning.

New York acts as Holden’s escape from Pencey. When he leaves Pencey Prep, he hails New York as an escape or a chance to seclude himself. Holden’s view of New York keeps changing throughout the novel — as does his perception of himself. “Rereading the book, I was struck by what an integral role Manhattan itself plays in the narrative. It’s not just that the city is the stage for much of the book’s action, or that Holden drifts through a fair number of the city’s famous attractions. It’s that Holden’s relationship to the city (love-hate, as it is for all of us) is such an integral part of who he is. He is not just in Manhattan, he is of it, a condition which, for better and for worse, I share myself.”(Beller, Thomas. Holden’s New York. The New Yorker, July 22nd, 2001.). He seems to find solace and comfort in the hustle-bustle of the city that he can’t seem to find elsewhere. His mind always seems to be in New York. It embodies the space of the novel as a central character as he’s narrating from the facility he’s confined in, and his mind even wanders to the ducks in Central Park when he’s talking to Mr. Spencer. He even holds double standards when it comes to the city — he complains about how cold it is at Pencey Prep, while in New York, the cold is a passing remark. However, New York is where Holden reaches his low, and when he’s at his low, Holden criticises. He criticises the people, the government, the culture, and the places. Nevertheless, he does long for companionship and realises that connecting with people is the only way to overcome his instability. The city provides a constant stream of people to do this with, and he does, after all, frequent the nearest phone-booth at all times.

Holden’s view of himself keep fluctuating throughout the novel — it is even described by many as his path to a mental breakdown. As his mental health and his perception of himself keeps changing, his perception and relationship with the city keep changing. Sometimes, it is as unforgiving to him as it would be to tourists (all of whom he holds in contempt), but it sometimes takes on the role of an old friend. Holden sees in New York conflicting versions of himself that he has grown to love and hate — partly his ideal self, and partly what his life is like — which is why his perception of the city keeps changing.

In the case of himself while the events are ongoing — New York is the setting for his mental deterioration into an ultimate breakdown. As his instability increases, his view of himself changes, as does his view of New York. He at first, seems mildly amused and even fascinated by the events that take place at the Edmont hotel he stays at chalking it down to the regular antics of the people in the city. “The trouble was, that kind of junk is sort of fascinating to watch, even if you don’t want it to be” — it’s at this point that Holden is optimistic about his prospects in New York. He’s relatively stable, has money to spend, and people to meet — the world is his oyster.

However, after he leaves the hotel to go to the Lavender Room, he is blatantly rejected by women he categorized as phonies. After tolerating him for a while, they begin to laugh at him; they also depress him by being obsessed with movie stars. New York takes on a new light for him when he’s leaving the bar — “New York’s terrible when somebody laughs on the street very late at night. You can hear it for miles. It makes you feel so lonesome and depressed”.

After this, as he’s heading to Ernie’s, he begins to tread unfamiliar ground — the cab driver, Horowitz is impatient and short with him — and he goes to Ernie’s, criticising it far more than he did the Lavender Room.

The next step in the narrative is when he makes a date with Sally Hayes — it’s at this point that he’s the most unstable he’s been throughout the novel — he “feels like marrying her the moment I saw her”, even though she seems to be the person he criticises the most. The play they watch just frustrates him. It’s now that he’s the most disillusioned with New York than he ever has been — he criticises everyone — George from Andover, Sally, The Lunts, Hollywood. “I sort of hated old Sally by the time we got in the cab, after listening to that phony Andover bastard for about ten hours.”, he says of his date. They go to Radio City, and he gets even more frustrated — at himself, Sally, the people watching them skate for no reason. He even wants to escape to Vermont or Massachusets, which he suggests to Sally, an act he chastises himself for multiple times after that — calling himself a “madman”. He’s so disillusioned with himself at this rate — he’s spent all his money, and the only slightly meaningful conversation he’s had has been with the three nuns in Grand Central Station — whom he keeps searching for. He seeks companionship after this disaster of a date — so he makes arrangements with Carl Luce — a boy he hasn’t seen in little over two years — which just shows how desperate he is for any sort of companionship to anchor him. They go to The Wicker Bar, which is chaotic and bustling with people. Earlier, he seemed to thrive on the turbulent environment of the city (such as at Grand Central, where he converses with the nuns), but now, his view of himself is deteriorating even further, as he becomes suicidal and reckless in his behaviour. Carl Luce is patronising throughout the conversation and even suggests that he get therapy. This doesn’t sit well with Holden, as he gets drunk and goes to Central Park, where he develops what is most likely pneumonia. “It was very cold and there was no one around anywhere.” — the city is as unforgiving to him as it would be to anyone else — and it also represents his life at the moment — ‘lonesome’.

There are fluctuations in his view of himself and his ultimate view of New York at that moment — which show how synonymous the changes in his perceptions of New York are with his attitude towards himself. He teeters between the love and the hate because he sees his ideal world in New York- which is why he’s so attached to the city. The example of The Museum of Natural History is perhaps the most important — he finds solace and comfort in what he considers a utopia. He goes to the Museum before his date with Sally after having a conversation with the nuns — which he felt was the most stimulating conversation he’s had throughout the course of his excursion. In the context of the conversation, the city changes completely for him — it’s now the closest he can get to a utopia. He delights in the sight of children skating in Central Park — carefree without the weight of adulthood on their shoulders. He then goes to the Museum, revelling in how “The best thing, though, in that museum was that everything always stayed right where it was.”. However, he turns away at the last moment, realising that he’ll never be able to achieve what he wants — not changing. As a teen on the cusp of adulthood who prizes innocence in children, he realises that he’ll never be able to achieve that coveted goal, and goes on a date with Sally — where, needless to say, he essentially equates everyone and everything in the city to the scum of the earth, ne’er-do-wells.

Perhaps the most important is the penultimate carousel scene. Holden is intent on leaving New York to go to Massachusets or Vermont — until he goes to Central Park with Phoebe and decides to stay, a decision made completely out of the blue. The chapter ends with Holden watching Phoebe ride on the Central Park carousel. “I was damn near bawling, I felt so damn happy.” But he doesn’t know why he’s happy, or why he’s on the verge of crying. He’s relieved after what seemed to be a long depression — through the epilogue, the reader knows that Holden is speaking from a facility near Hollywood after he decided to stay in New York. In the end, Holden is truly at a low, while the self-destructive and suicidal tendencies that he’s been harbouring are at a high. Seeing Phoebe on the carousel, however, convinces him to stay in New York — as he changes his perception based on the sight in front of him. Staying in New York symbolises him letting go of these tendencies to be in a city he truly has a love-hate relationship with at the end of the novel. On one hand, the city has treated him like it would treat any other newcomer, while on the other hand, it’s provided him with some semblance of an identity — The Catcher in The Rye, via the little boy singing the song when he’s walking down the street.

Thus, Holden’s relationship with New York represents his relationship with himself. He does, indeed have what some would call a love-hate relationship with himself, as well as with the city itself. As his mental health declines, his perception of New York changes completely — it goes from a haven to hide out for some time to the root cause for all his complaints. The fluctuations in his moods, as well as his perception of himself, also change his attitude towards the city. The city of New York can be treated as a character in the novel — in the narration, it treats Holden exactly the way Holden thinks of it.


Annie Hall, Dir. Woody Allen, Perf. Diane Keaton and Woody Allen, United Artists, 1977. Film.

Moore, R. (1965). The World of Holden. The English Journal,54(3), 159–165. doi:10.2307/811333

Seng, P. (1961). The Fallen Idol: The Immature World of Holden Caulfield. College English, 23(3), 203–209. doi:10.2307/373007

Beller, Thomas. Holden’s New York. The New Yorker, July 22nd, 2001.

Costello, D. (1959). The Language of ‘The Catcher in the Rye’. American Speech, 34(3), 172–181. doi:10.2307/454038

Trowbridge, C. (1966). The Symbolic Structure of “The Catcher in the Rye”. The Sewanee Review, 74(3), 681–693. Retrieved May 1, 2020, from www.jstor.org/stable/27541452

Edwards, D. (1977). Holden Caulfield: “Dont’t Ever Tell Anybody Anything”. ELH, 44(3), 554–565. doi:10.2307/2872573