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17 of the saddest songs ever

November 15 2016, 12:33 PM EST By Philip Trapp


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.

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