17 of the saddest songs ever

November 15, 2016

Sometimes, a sad song can help us absorb and understand the tragedies in life. Here are 17 songs we think are the saddest ever.

Death Cab For Cutie – “I Will Follow You Into The Dark”

The perfect combination of romance and rumination, Ben Gibbard’s solo serenade of ominous adoration tugs at the heartstrings and evocatively illustrates the hereafter. “I Will Follow You Into The Dark” sells a death that stings less when one’s passionately trailing a lover into the underworld. “Love of mine, someday you will die.” And so will we all.

Fall Out Boy – “Golden”

Arguably the most heart-rending Fall Out Boy song yet released, Infinity On High‘s piano-driven “Golden” can make mincemeat of any melancholy music lover. Co-written with Cold Cave’s Wesley Eisold, Pete Wentz’s profoundly forlorn lyrics (vocalized by Patrick Stump’s wistful wail) evoke loneliness and failure in a way that few other bands can match.

Brand New – “Play Crack The Sky”

The last track on the band’s breakthrough Deja Entendu, “Play Crack The Sky” tells the sorrowful tale of a mid-century shipwreck in Montauk, New York, resulting in the loss of 45 lives. As if to add levity to the morbid narrative, frontman Jesse Lacey cheekily apes the Beatles‘ famous Sgt. Pepper’s repeating run-out groove at the very end of the cut.

The Wonder Years – “Cardinals”

A serpentine strain of remorse from the Wonder Years‘ recent No Closer To Heaven, “Cardinals” likens a bird’s kamikaze mission to the frittered ashes of blown opportunity and forfeited friendship. “We’re no saviors if we can’t save our brothers,” the song’s bridge, repeats the sole lyric of Heaven‘s intro track, “Brothers &”—the tandem suite seemingly referencing the death of a close band associate.

Jimmy Eat World – “Goodbye Sky Harbor”

Also a nod to the band’s hometown Phoenix airport, “Goodbye Sky Harbor” recounts the ending of John Irving’s 1989 novel, A Prayer For Owen Meany. Spoilers ahead: In a terminal bathroom at the titular airport, the book’s main character saves a group of children from a live grenade, dying from blood loss and morbidly fulfilling a lifelong premonition of martyrdom in the process. “He said: ‘I am but one small instrument.'”

Weezer – “Butterfly”

“Yesterday I went outside with my momma’s mason jar.” Go to a quiet corner, put on your best pair of headphones and play Pinkerton‘s closing song for a master class in symbolic, sentimental storytelling. “Butterfly” wraps up relations, romance and regret into one beautiful, blooming parable of woe. Wait for the final sigh (it’s there) and feel free to cry.

American Football – “Never Meant”

The starting soliloquy on American Football‘s influential 1999 debut album, “Never Meant” is a pithy but practical send-off to a squandered relationship. The recently-reunited Mike Kinsella vehicle’s spindly guitars, lockstep drums and heartfelt vocals were the soundtrack to a million suburban breakups throughout the 2000s. Is it better to have loved and lost than never to have loved at all? “You can’t miss what you forget.”

Real Friends – “If I Had A Heart”

When a song begins with a deathwish on ice, you know you’re in for a rueful rumination of past gaffes. Real Friends‘ contribution to Fearless Records’ 2013 Punk Goes Christmas compilation is a desolate yuletide yarn of seasonal solitude. Apparently, singer Dan Lambton’s grandma also listens to American Football, repeating the cornerstone “Never Meant” line (“You can’t miss what you forget”) to the Real Friends vocalist, in song.

Dashboard Confessional – “Screaming Infidelities”

The exemplar Dashboard Confessional ditty, “Screaming Infidelities” has been a staple emo breakup jam for nigh on two decades. A testament to Chris Carrabba’s strengths as a songwriter, the tearful tune is still a showstopper at Dashboard gigs today. Meta sad points for being one of the saddest songs about listening to “the saddest songs.”

Twenty One Pilots – “Truce”

A slow-burning plea from the band’s third studio album, Vessel, “Truce” makes the tearful case for continuing life in the face of unabating calamity. “The sun will rise and we will try again,” sings Tyler Joseph, lamenting certain and eventual death but exhibiting hope for the future.

My Chemical Romance – “Cancer”

Recently covered by Twenty One Pilots, My Chemical Romance‘s “Cancer” is a mournful but unfeigned account of the namesake disease whereby cells divide and ruin lives. The track appears on MCR’s milestone The Black Parade album, which recently marked its 10th anniversary as celebrated by AP.

Blink-182 – “Stay Together For The Kids”

One of Blink’s best songs, and by far their best sad song, Take Off Your Pants And Jacket‘s third single is a dogged description of divorce from the perspective of a dejected juvenile. The finest pop song of its kind.

The Killers – “Believe Me Natalie”

“Believe Me Natalie” has just the right amount of maudlin humor and droll despair to make it one of the Killer‘s best sad songs. The nostalgic, personal nuance is what makes it: “Remember the arch of roses right above your couch?”

Years & Years – “Memo”

An earth-shattering slow jam from the British electronic group’s 2015 debut album, Communion, “Memo” documents a forbidden love affair that’s doomed to fail. Singer Olly Alexander’s steamy falsetto floats along the catchy beat in a way that feels dangerous.

Radiohead – “Videotape”

Toying with the pseudo-Evangelical idea of viewing a demo reel of your deeds at heaven’s gate, and/or the more general notion of your life “flashing before your eyes” at death, Thom Yorke wrote the saddest-ever song about spending a day with the kids.

Panic! At The Disco – “The End Of All Things”

Brendon Urie’s heartfelt declaration of love to his wife, “The End Of All Things” promises his feelings will “remain the same” when everything else around him changes. The sweetly sad, robotic melody—backed by appropriately apocalyptic piano and strings—builds to the linchpin line, “Lay us down, we’re in love.”

The Smiths – “I Know It’s Over”

“Oh mother, I can feel the soil falling over my head.” The Smiths’ “I Know It’s Over” is the ultimate woebegone breakup song for those feeling “less than” at life. Morrissey and Marr (pretty much) only wrote sad songs, and this is one of the absolute saddest. Bonus points to the lads for the brilliant contrast of maternal and romantic love. “Oh well, enough said.”