What Is The Most Depressing Song on the ‘Inside Llewyn Davis’ Soundtrack?

By  · Published on December 11th, 2013

If it seems as if we’ve been covering the soundtrack from the Joel and Ethan Coen’s newly released Inside Llewyn Davis quite a bit around these parts as of late, that’s a totally fair observation, simply because it’s true. The sixties-set film about the eponymous New York City folk singer that never hit the big time is appropriately steeped in music, and all of it just so happens to be damn good. Inside Llewyn Davis is one of the best films of the year, but its soundtrack is easily the best soundtrack of the year.

But if something like “Please Mr. Kennedy” is an unabashedly joyful jam (and it is) that proves that not all folk music needs to be morose and depressing (it does not), where does that leave the sadder songs of the soundtrack? Turns out, in pretty good standing, because while the Inside Llewyn Davis soundtrack may feature some upbeat compositions, it’s still packed to the gills with the kind of stuff that might make you consider ending it all (and that’s not hyperbolic – as we soon discover in the film that Llewyn’s former singing partner did just that before the action of the film unfolds). So what’s the saddest song on the Inside Llewyn Davis soundtrack? Behold – an investigation.

1. “Hang Me, Oh Hang Me,” Oscar Isaac
The first song that Isaac sings in the film includes plenty of talk about hanging, laying in the grave, and the terribly embarrassing brag that he’s been to “parts of Arkansas,” but despite all those depressing bits of characterization (parts! Just parts! Of Arkansas!), “Hang Me, Oh Hang Me” stands as a good introduction to Llewyn’s style more than anything. Sad stuff, but nothing that can’t be overcome with a stiff drink

2. “Fare Thee Well (Dink’s Song),” Oscar Isaac & Marcus Mumford
This soaring little number is the one that’s been trotted out for the bulk of the film’s marketing, and if you’ve only heard it in the context of a commercial or TV spot, sure, it sounds plucky and a touch uplifting – ha! Ha! HAHAHAH! Enjoy hearing it within the film itself and brace yourself for the sudden realization that Mumford serves as the voice of Llewyn’s beloved dead partner. “Fare thee well, my honey” indeed. Is life worth living without the one you love? You decide. (The answer is no.) It’s the best song on the entire soundtrack, but it’s also the most haunting.

3. “The Last Thing On My Mind,” Stark Sands With Punch Brothers
Clear-voiced, a bit plinky-plunky, and a good way to recover from the gut punch of “Fare Thee Well,” but not depressing in the slightest.

4. “Five Hundred Miles,” Justin Timberlake, Carey Mulligan, & Stark Sands
Justin Timberlake’s Jim is well-meaning, generous, sweet, and talented. He’s also entirely devoid of emotional intelligence and anything resembling street smarts. Carey Mulligan is Jean, his hard-nosed girlfriend who can’t seem to forgive anyone else for her Llewyn-centric transgressions. Jean and Jim are a beloved little duo, but it’s hard to feel sad while listening to them, simply because it’s a whole hell of a lot easier to want to smarten them up. Wise up, kids.

5. “Please Mr. Kennedy,” Justin Timberlake, Oscar Isaac, & Adam Driver
Outer. Space. UH OH. This is the exact opposite of depressing, this thing is life-affirming.

6. “Green, Green Rocky Road,” Oscar Isaac
Here’s the only sad thing about this folk jam – it shows just how talented Llewyn really is, even in the calmest and quietest moments.

7. “The Death of Queen Jane,” Oscar Isaac
Ditto this one.

8. “The Roving Gambler,” The Down Hill Strugglers with John Cohen
We’re too busy promenading to be sad.

9. “The Shoals of Herring,” Oscar Isaac with Punch Brothers
Only Oscar Isaac could make the word “herring” sound mournful.

10. “The Auld Triangle,” Chris Thile, Chris Eldridge, Marcus Mumford, Justin Timberlake, & Gabe Witcher
This is essentially the work of an Irish barbershop quartet who show up Llewyn by way of their natty sweaters and swanky haircuts (at least, within the context of the film itself), and so while the song itself isn’t sad, what it means is horribly sad – Llewyn, you’re not going to make it. They are.

11. “The Storms Are on The Ocean,” Nancy Blake
Achingly authentic, instantly classic, and a damn fine reason to get in a bar fight.

12. “Fare Thee Well (Dink’s Song),” Oscar Isaac
Can’t write, can’t talk, too sad, choking back tears.

13. “Farewell,” Bob Dylan
Don’t be sad for Bob Dylan, he’s going to make it! (But he also get the second most depressing song to go with that distinction.)

14. “Green, Green Rocky Road,” Dave Van Ronk
Here’s to you, Dave, and here’s to your talents.

The verdict? “Fare Thee Well.” Inside Llewyn Davis is about a lot of things – cultural progression, dreams deferred, bad money management, insurmountable mistakes, cats – but at its heart it’s really about what happens when someone you love leaves you in the worst possible way and you’re unable to pick up the pieces. “Fare Thee Well” is accomplished in all the best ways, it’s catchy and smart and soaring, but it’s also infused with a deep sense of loss that only becomes more evident as the film winds on. Fare thee well.

Inside Llewyn Davis is in theaters now. The Inside Llewyn Davis is available purchase at the usual places.