Literary Mixtape: Holden Caulfield


If you’ve ever wondered what your favorite literary characters might be listening to while they save the world/contemplate existence/get into trouble, or hallucinated a soundtrack to go along with your favorite novels, well, us too. But wonder no more! Welcome to the first installment of a new feature on Flavorwire, where we sneak a look at the hypothetical iPods of some of literature’s most interesting characters. What would be on the personal playlists of Holden Caulfield or Elizabeth Bennett, Huck Finn or Harry Potter, Tintin or Humbert Humbert? Something revealing, we bet. Or at least something danceable. Read on for a cozy reading soundtrack, character study, or yet another way to emulate your favorite literary hero.

Holden Caulfield is the king of all disillusioned youth, an angst-ridden teenager slouching from dorm room to city street to dance hall with general indifference and a real lousy attitude. There are about a million songs about him, which are pretty well documented, but what would the fellow listen to himself? He would surely think pop music is completely phony, and probably wouldn’t be interested in anything anyone he knew liked, but he’s an asocial, introspective depressive, so we’re pretty sure he’d get a kick out of some of the same songs that got us through our teenage years – if he’d like anything at all, that is.

Disclaimer: We have made little to no effort to remain true to time period. After all, Holden Caulfield didn’t even have an iPod, obviously. Try and suspend your disbelief.

“Mad World” (Tears for Fears Cover) – Gary Jules

Worn out places and dreams of dying? Holden finds it all pretty hard to take, too.

“E is for Estranged” – Owen Pallett

“Pathos is born/ born out of bullshit in formal attire”

“Heaven Knows I’m Miserable Now” – The Smiths

It is Holden Morris(s)ey Caulfield, after all.

“Between the Bars” – Elliott Smith

Both metaphorically and literally.

“Sing, Sing, Sing” – Benny Goodman & His Orchestra

Holden sure does appreciate a girl who can dance the jitterbug, even if she’s completely dopey.

“I Hate My Friends” – Sebastien Grainger

Stradlater and Ackley kid? Who wouldn’t?

“I’m So Depressed” – Abner Jay

Abner goes straight from joking and ogling women to singing about his depression. It’s important to cover your bases.

“Three Cool Cats” – The Coasters

Those phonies would just kill him.

“The State I Am In” – Belle & Sebastian

Some state or other. Not to be confused with Le Pastie de la Bourgeoise, which name drops the book.

“Something Vague” – Bright Eyes

Because if Holden Caulfield doesn’t listen to Bright Eyes, we don’t know who does.

“Cars & Telephones” – Arcade Fire

That’s just about all there is, isn’t it?

“She Sends Kisses” – The Wrens

Always waiting on the idea of a certain girl can take a toll on a guy.

“One Man Guy” – Rufus Wainwright

“Don’t ever tell anybody anything. If you do, you start missing everybody.”

“The Only Living Boy in New York” – Simon & Garfunkel

And barely, at that.

Anything we missed that you think Holden would have on repeat? Let us know in the comments!