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…”

Sufjan Stevens — “Chicago”

The centerpiece of Stevens’ rambling masterpiece Illinoise is a simple travelogue of a voyage to the Windy City and back… and yet, it’s also so much more than that. For all the at the lyric’s ostensibly pretty simple — it apparently catalogues a journey the singer and a couple of friends to the city for a weekend when he was 19, when they were broke and ended up staying with a couple of homeless men in an old school, and contrasts that trip with a later visit to New York — it also embodies many of the central themes of Illinoise, including self-discovery, change, renewal, the desire to run away and start again, and the discovery that ultimately it’s not where your body is that matters… it’s where your heart is that counts.

Nick Cave & the Bad Seeds — “In the Ghetto”

Yes we KNOW this is a cover version (although, it has to be said, Elvis didn’t write “In the Ghetto” either — it was in fact penned by Texan songwriter Mac Davis). We just happen to have a soft spot for Cave’s version, which was his very first single with the Bad Seeds and features a video that looks like it was shot in his parents’ garage (in fact, it was shot in the garage of a house in LA, where Cave was living at the time). Anyway, whichever version you choose, this is a fantastic song about the atavistic social ills of poverty, set against the backdrop of a “cold and grey Chicago morn.”

Marshall Jefferson — ”Move Your Body”

Wait, can a track whose lyrics have pretty much nothing to do with Chicago still be about Chicago? We say: yes. This is perhaps the quintessential Chicago house track, and the spirit of the city in the mid-1980s permeates every aspect of its sound — it’s a record that makes you feel like you actually really are at some sweaty mid-Western warehouse party in 1987, even if (like Flavorpill) you were all of nine years old at that point.

Dr West’s Medicine Show & Junk Band — “The Eggplant that Ate Chicago”

So… maybe the acid really was better back in the ’60s, eh? (Sorry for the bodgy video, by the way — there’s a better version here, but it has embedding disabled.)

Robert Johnson — ”Sweet Home Chicago”

The Great Migration that brought some six million African-American workers into the North increased Chicago’s population by some one million people between 1900 and 1920. The immigrants brought their music with them out of the south, and by the mid-20th century, Chicago was the home of the blues north of the Mason-Dixon line. There have been many fantastic Chicago-based blues musicians since — Buddy Guy, Muddy Waters and Bo Diddley spring to mind immediately — but if there’s one blues song that’s become a de facto anthem for blues and the Windy City, it’s Robert Johnson’s 1936 depiction of the city as some sort of distant promised land (indeed, he equates Chicago with California, a lyric that’s inspired much debate over the years). In the 75 years since Johnson’s version was released, “Sweet Home Chicago” has been covered by everyone from Fleetwood Mac to The Replacements — but we still like the original best.

Blur — The Great Escape

For some reason, we’ve been listening to a lot of early/mid-period Blur of late, and particularly this album. Revisiting The Great Escape many years after the Great NME-Hyped Chart Battle of 1995, two things stand out about the album: a) how musically weird it is (especially Graeme Coxon’s guitar solos — see “Country House” and “Stereotypes” for examples) and b) how dark and misanthropic it is. Like all of Blur’s early work, the album’s populated by a rich cast of characters from a cross-section of English society, from the grotesque wife-swapping duo of “Stereotypes” and the charmless man of, um, “Charmless Man” to the forlorn taxi driver of “Best Days” and the star-crossed lovers of “Yuko and Hiro.” We’d love to see someone build a narrative around these characters and the theme of escape that dominates the album — we reckon the result’d be something like a modern take on The Fall and Rise of Reginald Perrin.

Scott Biram

“I kinda evolved into the one-man band thing,” says Scott Biram, aka the Dirty Old One Man Band, who began his career playing in punk and rock bands before developing a side solo career. “I started out just stomping my foot on the stage, then I started stomping on my mic stand. I just kept adding speakers, and experimenting with different stomp-board setups. I’ve gone through about five different designs over the years.” But even for a seasoned one-man band, Biram noted the challenges of going it alone. “After my other bands broke up, my solo stuff started to need more bang. I wanted to keep touring. I wanted to play in rock clubs still, but as a solo performer it was hard to get any gigs like that… I needed to build more of a presence.” Despite the challenges he’s faced, Biram has got it down. “Nowadays, if a four piece opens for me, there’s a good chance I’m just as loud as them, if not louder.” For the Sailor Jerry Presents show, Biram performs with Molly Gene: One Whoaman Band.

Click through below to check out all of our one-man band picks.

Zone One, Colson Whitehead

Mac Arthur Genius grant-winning author Colson Whitehead sixth novel is, inexplicably to some, about zombies. And it’s great. As Whitehead told The Atlantic, “When I was starting the book, I would say, ‘I’m writing a horror novel with zombies.’ And my sort of bookish friends would say [adopts a clipped, defensive tone]: ‘I don’t like zombies. I don’t like zombie books.’ And I’d ask them, ‘Well, what zombie books have you read? What zombie films have you seen?’ None. So people who are inside horror culture have their own ideas about zombies, and the people outside have their own stereotypes about zombies. What I tried to do with the book was embrace some of the conventions of the film genre, and reject others. By keeping what I like, and throwing out what I don’t, I hopefully can expand people’s ideas about this type of horror story.”

of Montreal — “Suffer for Fashion”

Avant-garde director and visual artist Sigrid Asturp utilized fast-forward stop-motion animation to create the bizarre series of vignettes for this offbeat music video. Featuring colorful, rubber glove-clad hands assembling objects, the clip finds inspiration in flamboyant frontman Kevin Barnes’ emotionally volatile lyrics, which reference the slavish following of trends, an idea that is visually represented through ever-evolving shapes and colors.

Noah and the Whale — “Life Is Life”
Poet: Charles Bukowski

The booze-soaked, overtly sexual poet and novelist has inspired many an artist, including British folk-pop outfit Noah and the Whale. The Charlie Fink-fronted band’s latest album title pays homage to Bukowski’s collection The Last Night of the Earth Poems, while this uplifting tune’s name and lyrics reference his poem “The Laughing Heart.”

For more Chiddy Bang, visit their official website, become a fan on Facebook, and download their new mixtape for free.

Also be sure to check out more artists in the Flavorpill Interactive Interview Series, including Theophilus London, Michael Showalter, and Morgan Spurlock.

The Five Stairsteps — “Ooh Child”

I know what song I want played at my funeral: “Days” by the Kinks. It just sums up everything so neatly. But the first song that came into my head as the last one to hear before I pass is the same song that always seems to enter my head first: “Ooh Child” by the Five Stairsteps. Because it’s the song that makes me feel happiest, every time I hear it. And why not go to the next bardo with a smile on my face?

– Ann Powers

Surfer Blood, Astro Coast – Brent Couchman