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Sad Indie Playlist: 21 Songs That Will Make You Weep

Sometimes, you just need a good cry... while also listening to the hippest artists of the indie rock boom. Here are 21 songs that allow you to wallow, from Bat For Lashes to Bon Iver, from Lykke Li to Antony

1 / 21

Sufjan Stevens, “Casimir Pulaski Day”

A six-minute tale of young love spoiled by cancer, that may very well be Sufjan Stevens’ best song? Yeah, that’s making this list.

2 / 21

Death Cab For Cutie, “I Will Follow You Into the Dark”

“Love of mine / Someday, you will die,” is a gutsy way to begin a song, but Ben Gibbard and co. pull it off with aplomb. Romantic and eerie, but deeply affecting.

3 / 21

Fiona Apple, “Left Alone”

Fiona Apple has said that this is her favorite song on The Idler Wheel…; it’s certainly the bleakest. “How can I ask anyone to love me / When all I do is beg to be left alone?” she wonders.

4 / 21

Antony & The Johnsons, “Another World”

Imagine reading the stats on climate change and realizing, “Welp, there’s no hope.” This is the sonic equivalent of that “Welp.”

5 / 21

Okkervil River, “A Stone”

Will Sheff’s croaking in the final minute of this song is devastating—it’s the moment when unrequited love provokes defeat instead of anger.

6 / 21

The Antlers, “Kettering”

There’s nothing sadder in the indie universe than the Antlers album Hospice, about a relationship between a hospice worker and a patient; “Kettering” packs the heaviest punch, especially as it winds down from its cacophony.

7 / 21

Bon Iver, “Re: Stacks”

Perhaps the most crushing line on this whole list: when Justin Vernon sings on “Re: Stacks,” “Whatever could it be that has brought me to this loss?”

8 / 21

Joanna Newsom, “Clam, Crab, Cockle, Cowrie”

The crown jewel of Joanna Newsom’s debut album The Milk-Eyed Mender, “Clam, Crab, Cockle, Cowrie” finds the singer at her most despondent, ending the album with a plea for love and attention.

9 / 21

Iron & Wine, “Sodom, South Georgia”

So much of Our Endless Numbered Days belongs on a Sad Indie playlist, but “Sodom, South Georgia” directly addresses the death of the narrator’s father, and thus is a touch sadder than the rest of the album.

10 / 21

Lykke Li, “Sleeping Alone”

I Never Learn is an impossibly sad breakup album, and Lykke Li saved its most heart-wrenching moment for its finale. “Sleeping Alone” finds the singer-songwriter accepting reality: She no longer has someone to wake up with.

11 / 21

The Mountain Goats, “Woke Up New”

Shout-out to John Darnielle for titling the saddest Mountain Goats album something as succinct as Get Lonely, and for making its lead single about something uniquely tragic—the first day following a breakup.

12 / 21

Vampire Weekend, “Hannah Hunt”

Vampire Weekend is not exactly known for its dour material, but “Hannah Hunt” is a beautiful bummer about realizing there’s no future with someone you care about. The fire, alas, cannot be rekindled.

13 / 21

Bat For Lashes, “Moon and Moon”

When you miss your beloved and know they’re staring at the same moon as you but from somewhere far, far away… yeah, that’s pretty sad.

14 / 21

Beck, “Lost Cause”

Is Sad Beck also the Best Beck? Sea Change makes a compelling argument, and the gorgeous “Lost Cause” captures the feeling of hopelessness in a relationship.

15 / 21

Wilco, “Jesus, Etc.”

A breathtaking reflection on 9/11, “Jesus, Etc.” finds Wilco at its most measured; even if you’re not into dad-rock, it’s worth embracing.

16 / 21

TV On the Radio, “Will Do”

“I think we’re compatible / I see that you think I’m wrong” is certainly one way to express unreturned feelings of love, but “Will Do” sadly soldiers on, pledging allegiance to someone who can never reciprocate that tenderness.

17 / 21

The National, “Start a War”

The juxtaposition between the sorrowful chime of the guitars and the desperation of the narrator’s attempt to fix his relationship woes (“Whatever went away, I’ll get it over now / I’ll get money, I’ll get funny again”) is the National at their very best.

18 / 21

Modest Mouse, “Lives”

Hey guys, our time on this earth is limited! Isaac Brock and the rest of Modest Mouse know that, and they also know that, unfortunately, it’s difficult to remember to press the pause button and embrace that fact.

19 / 21

Björk, “Stonemilker”

The rumblings of a devastating breakup exist in the roots of “Stonemilker,” the opening of Björk’s most recent album, Vulnicura. The prelude to chaos here is more compelling than the actual awfulness.

20 / 21

Bright Eyes, “Lua”

Substance abuse and fear of commitment color this Bright Eyes fan favorite, with Conor Oberst’s voice quivering when he declares, “The love I sell you in the evening / By the morning won’t exist.”

21 / 21

Grizzly Bear, “Foreground”

Hard to believe that something this sad is on the same album as “Two Weeks,” huh? Well, you better believe it, Grizzly Bear novice!

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