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Yeah, he just got kicked out of prep school, but this seventeen-year-old is smarter than he gives himself credit for. And okay, he’s judgmental and cynical, and the list of things he has contempt for is never-ending, beginning with grown-ups and phonies. Nevertheless, despite his prickly nature, he’s also honest, vulnerable, and protective of what little innocence he sees in the world. Holden Caulfield has become a poster boy for teen alienation, which is something he’d probably hate. In honor of the original Mr. Misunderstood, here's a playlist to cultivate one's disillusionment.

“Teen Angst (What The World Needs Now)” - Cracker

Apart from its highly appropriate title, there’s a disdain and self-deprecation in this song Holden would truly appreciate. Particularly the jokey arrogance and ambivalence of the opening lines:

“I don't know what the world may need
But I'm sure as hell that is starts with me
And that's a wisdom, I've laughed at”

 

“Mad World” – Tears For Fears  

We’re not sure if Holden might have preferred the sadder, more downtempo Gary Jules cover or found it phony, so we’ll stick to the original, just in case. Either way, the existential malaise of this song gives our sulky hero a perfect inner soundtrack: 

“All around me are familiar faces
Worn out places
Worn out faces
Bright and early for their daily races
Going nowhere
Going nowhere”

 

“Zero” – The Smashing Pumpkins

Billy Corgan has written a lot of songs that speak to disaffected youth but there’s a poetry in his angst we think Holden would be especially drawn to. Consider:

“Intoxicated with the madness, I'm in love with my sadness
Bullshit fakers, enchanted kingdoms
The fashion victims chew their charcoal teeth
I never let on, that I was on a sinking ship
I never let on that I was down”

 

“Academy Fight Song” – Mission to Burma

A song about being disillusioned with school with a strong antisocial sentiment is a song Holden can get behind. Surely he can also identify with the self-awareness the lyrics reveal behind the narrator’s outward disdain:

“Maybe you're right
I shouldn't judge
What's wrong or right
This is too much
I'm not judging you, I'm judging me”

 

“Who Wrote Holden Caulfield” – Green Day

The Catcher in The Rye is Green Day lead singer Billie Joe Armstrong’s favorite novel, so it’s no surprise he wrote a song about its protagonist:

“There's a boy who fogs his world and now he's getting lazy
There's no motivation and frustration makes him crazy
He makes a plan to take a stand but always ends up sitting.
Someone help him up or he's gonna end up quitting”

 

“Kid” – The Pretenders

We won’t assume Chrissie Hynde wrote this song for Holden Caulfield, but we could imagine him taking great comfort from the lyrics, which talk of sorrow and growing pains:

“Kid what changed your mood
You've gone all sad so I feel sad too
I think I know some things we never outgrow
You think it's wrong
I can tell you do”

 

“There’s Always Someone Cooler Than You” – Ben Folds

This is one tuneful manifesto for misfits. The lyrics are a call to drop pretenses and stop worrying what other people think about you.

“Smile
Like you've got nothing to prove
No matter what you might do
There's always someone out there cooler than you”

 

“United States of Whatever” – Liam Lynch

This song has a frenetic guitar, a shrieking chorus, and lyrics full of indifference and antipathy, all of which we can imagine Holden being a fan of.

“Then this chick comes up to me and she's all, like,
‘Hey, aren't you that dude?’
And I'm, like, ‘yeah, whatever!”

 

“I’m Just A Kid” – Simple Plan

We had to include some emo here. If Holden was in a band, we imagine he’d write songs exactly like this one. Case in point:

“I'm just a kid and life is a nightmare
I'm just a kid, I know that it's not fair
Nobody cares, cause I'm alone and the world is
Having more fun than me”

 

“The Boy With The Thorn In His Side” – The Smiths

We can’t say for sure whether we believe Holden would’ve thought Morrissey was a phony, but we have a hunch he would’ve appreciated Moz’s wit and raw emotions, especially here:

“The boy with the thorn in his side
Behind the hatred there lies
A plundering desire for love”

 

What else should be on Holden Caulfield’s playlist? Not that he cares or whatever. Tweet your suggestions at @QuirkBooks, or don't, I guess. 

Full Playlist: 


Margarita Montimore's picture

Margarita Montimore

Margarita writes upmarket fiction and is represented by Victoria Skurnick at Levine Greenberg Rostan. She also transcribes and pokes fun at her old journal entries at The Diary Project. When not wrangling her ever-growing book and movie collections or feeding squirrels and chipmunks, she dreams of the day time machines are built so that she can return to the 1980s. Follow her on Twitter at @damiella.