Literary Mixtape: Eeyore


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! Here, 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. This week: Winnie the Pooh’s most mournful pal, Eeyore.

Christopher Robin’s old grey donkey is the gloomiest animal in all of the Hundred Acre Woods. Even his home is labelled “Eeyore’s Gloomy Place: Rather Boggy and Sad” on the map (he keeps a house made of sticks there, though it falls down all the time). Eeyore is depressed and pessimistic, but he’s not just your average soggy stuffed animal. He’s also one of the few animals to be able to read and write, and the only animal besides Pooh to write poetry. And like most sad poets, he has a rather low opinion of the intelligence of his Hundred Acre brethren, sniffing that they have “No brain at all, some of them, only grey fluff that’s blown into their heads by mistake, and they don’t Think.” That sounds like a pretty clear angsty artist to us, stuffed donkey or no. We think it’s pretty obvious that poor old Eeyore would have an iPod full of sad sack songs, but he wouldn’t go in for the really hard depressing stuff. We know he’s got a soft, squishy inside. Here’s what we think Eeyore would mope, get rained on, and beat everyone in Poohsticks to.

Stream the mixtape here.

“Blue” — Joni Mitchell

How could a committed depressive like Eeyore not appreciate a song called “Blue?” It is sure to be his favorite foggy lullaby.

“Milk Thistle” — Conor Oberst

Thistles, you may be aware, are Eeyore’s favorite food. If Conor Oberst, one of the kings of the sad sack indie rock ballad, is singing a song about them, you can bet Eeyore has it on repeat.

“Romulus” — Sufjan Stevens

To us, this is one of the saddest songs of Stevens’ oeuvre, but it also shows off a little bit of light at the end of the tunnel. Eeyore might play this over and over again while waiting to grow up himself.

“Autumn Sweater” — Yo La Tengo

It might just be us, but we always imagine the Hundred Acre Wood in the late summer. No matter what season, you can bet Eeyore’s always thinking of the autumn.

“Needle in the Hay” — Elliott Smith

What gloomy misanthrope’s mixtape would be complete without a little Elliott Smith? Eeyore would definitely rock the box set, but he might have a little more experience than most with hay.

“Lost Cause” — Beck

Eeyore’s not really a lost cause, but he sure likes to think he is. “‘We can’t all, and some of us don’t. That’s all there is to it,'” he tells Pooh. “‘Can’t all what?’ said Pooh, rubbing his nose. ‘Gaiety. Song-and-dance. Here we go round the mulberry bush.'” Wamp wamp.

“I Know It’s Over” — The Smiths

You know the song is depressing when the third line is “Oh well. Enough said.” That sounds right up Eeyore’s alley to us.

“Hallelujah” — Jeff Buckley (Leonard Cohen cover)

We think Eeyore would curl up to sleep to this desperately sad and heartbreakingly beautiful number. But hey, doesn’t everyone at least once in their life?

“Comfortably Numb” — Pink Floyd

We think a donkey who counts the days since anyone spoke to him would nod glumly along with the intro to this song.

“Another Man’s Done Gone” — Billy Bragg & Wilco

Ultimately, it might just be a kind of apathy: “Well I don’t know/ I may go/ Down or up or anywhere…”