19 Sad Indie Songs, The Saddest Of All Time

Sometimes feeling bad feels so good. Music is a perfect and direct way to wallow in your sad emotions, and nobody makes sadder music than an indie musician with a guitar. Grab a box of tissues, and let’s look at some sad indie songs you may be able to relate to.

1. “Two” by the Antlers

Song Year: 2009

The Antlers’ 2009 album, Hospice, is a contender for the saddest piece of art ever created. “Two” is the cherry on top of that depressing sundae. The song tells the story of a young man watching his partner slowly die from a malignant illness.

“Two” details the way the lovers have come to resent each other, made worse by the isolation her condition has caused. The sickness caused a separation between the partners while alienating them from their friends, so they only have each other. The song is, to put it mildly, a massive bummer but a pretty-sounding one.

2. “Amy in the White Coat” by Bright Eyes

Song Year: 2006

“Amy in the White Coat” is a massive trigger warning of a song. The Bright Eyes’ song finds Conor Oberst whisper-singing the story of a girl repeatedly abused by her father.

The song is a brutal portrait of endurance. The melancholic tune lacks any hopefulness; the titular Amy is isolated, lonely, and abused, without any opportunity for escape.

3. “Needle in the Hay” by Elliott Smith

Song Year: 1995

Elliott Smith helped create the gold standard for sad indie songs. The singer-songwriter expertly layered thoughtful lyrics, his delicate vocals, and melancholy acoustic guitar to haunting effect in “Needle in the Hay.”

The song details the singer’s struggle with heroin, a subject matter that becomes more fraught when the listener considers Smith’s life-long battle with addiction.

4. “Sleep” by Azure Ray

Song Year: 2001

Azure Ray consistently finds the prettiness in their saddest songs. The duo of Orenda Fink and Maria Taylor harmonize beautifully, creating a soft, melancholy sonic blanket.

Listeners may not understand precisely why “Sleep” makes them sad, but trust that it will bum you out. The song’s lyrics are vaguely despondent and could be about a lost love or a personal journey. However, the words carry the veneer of sadness.

5. “Personal” by Stars

Song Year: 2007

“Personal” by Canadian band Stars is a hard listen. The song tells the cruel story of a couple communicating via personal ads. Torquil Campbell and Amy Milan sing the letters to each other as the pair get acquainted and decide to meet.

When the night comes for the couple to meet, the woman, who has previously expressed her insecurities and difficult history, waits. But the man never shows. She establishes in a follow-up letter that he came, saw her, and left because of her appearance.

6. “A Man/Me/Then Jim” by Rilo Kiley

Song Year: 2004

Rilo Kiley tells three stories of lost love in “A Man/Me/Then Jim.” The song examines how painful it is when passion fades away so slowly you don’t notice until it’s gone.

The song is a melancholy lament, buoyed by Jenny Lewis’s sparkling but empathetic vocals. Each character in the narrative suffers because of the gradual abating of affection, resulting in a feeling of isolation and alienation.

7. “I Get Overwhelmed” by Dark Rooms

Song Year: 2017

“I Get Overwhelmed” featured prominently in one of the saddest movies of the last several years, A Ghost Story. In a cracking falsetto, the singer tells the story of ennui. He’s disaffected and alienated; he and his girlfriend are unhappy and nearing a disaster point. Nothing massively awful has happened to him, but he still feels beaten down by depression.

8. “Flirted With You All My Life” by Vic Chestnutt

Song Year: 2009

Don’t be fooled by the title; “Flirted With You All My Life” is not a cute love song. Vic Chestnutt sings his beautiful song to death, with whom he’s had a contentious off-and-on relationship.

The singer has courted thoughts of suicide but ultimately doesn’t feel ready for the end. He discusses the cruelty of death, telling the story of his mother’s cancer battle. “Flirted With You All My Life” is beautiful but absolutely devastating.

9. “What Sarah Said” by Death Cab For Cutie

Song Year: 2005

“What Sarah Said” grapples with the impossible hopelessness of discovering someone you love is terminally ill and not being able to do anything about it.

The narrator discusses the complicated reality of loving someone, acknowledging that it inevitably means losing them. “What Sarah Said” posits that love means being present even when you can’t possibly impact the outcome of a difficult situation.

10. “The Ballad of Bird and Fox” by Don’t Stop or We’ll Die

“The Ballad of Bird and Fox” by Don’t Stop or We’ll Die

Song Year: 2010

Don’t Stop or We’ll Die applies a fairy tale lens to the complicated question of separation. “The Ballad of Bird and Fox” tells the story of a pair of woodland creatures who fall in love and have a little bird-fox child.

The couple begins to resent each other, each party claiming the child favors them. The pair resolves to move past their differences to give their son a happy life, but the underlying tensions remain. The song is shockingly effective; the adorableness of the animal lovers is immediately undercut by the very real and very human pain of a rotting love affair.

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