interesting 25 Depressing Stories Behind Some Of The Most Popular Songs In Modern History  

Mike Rothschild
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Sometimes a song can be uptempo and peppy, while also being crushingly sad, but sometimes a song is just crushingly sad. Many are based purely on their writer's imagination, but for these songs, real life proved far more depressing than anything a musician could come up with. These famous songs and memorable tracks might be upbeat or seem like a lot of fun, but they all have super sad and depressing backstories, that will have you rethinking using Van Halen's "Jump" on your pump up playlist.

You know Eric Clapton wrote "Tears in Heaven" about the death of his son, but what about the song "Circus"? Plenty of upbeat pop songs like "99 Red Balloons" and "Semi-Charmed Life" are actually about pretty dark subjects, like nuclear annihilation and addiction. As well, a number of the songs with sad meanings on this list were released posthumously, after the songwriter passed away, usually from reasons related directly to their sad song lyrics.

Here are songs that might be peppy, might be slow, might be epic - but all are based on really terrible things that actually happened. They might not seem like sad songs, but if you listen closely, you will likely shed a tear. Upvote the tracks and singles with the saddest true backstories below... but be sure to grab a box of tissues first.

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The Gordon Lightfoot story-song isn’t a fanciful creation – it’s the story of an actual ship sinking. The SS Edmund Fitzgerald was a real iron ore carrier that traversed the Great Lakes carrying ore pellets to various ports of call. Or she did, until she sank in a massive storm with the loss of her entire crew of 29 sailors - just like the song describes.
see more on Gordon Lightfoot - The Wreck of the Edmund Fitzgerald

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While obviously about drug addiction, it’s less well known that Neil Young wrote this song in 1971 about a specific person. Included on the 1972 album Harvest, “The Needle and the Damage Done” eulogizes the heroin addiction of his bandmate, guitarist Danny Whitten. As the story goes, while rehearsing for a tour, Young gave Whitten $50 and a plane ticket for LA – where Whitten would soon overdose. Young’s guilt was reflected in a number of later songs, most especially “Tonight’s the Night.”
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Fastball - The Way


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Pop band Fastball’s only hit, “The Way” tells a romanticized version of a real story – about two old people disappearing.

Lela and Raymond Howard left home in June 1997 to attend a festival in Texas, despite Lela suffering from Alzheimer’s disease and Raymond having recently had brain surgery. Their bodies were found two weeks later at the bottom of a ravine near Hot Springs, AR, hundreds of miles away from where they intended to go.
see more on Fastball - The Way

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Written as a tribute to Pink Floyd’s original creative mastermind, Syd Barrett, the recording of the this nine-part opus took a bizarre turn when, in January 1975, Barrett himself showed up at Abbey Road Studios – while the band was recording the song about him. At first, nobody recognized Barrett, who’d gained weight and shaved his head since being ousted from the group years earlier. He hung around awhile, and offered to play on the track, but was in no shape to do so.

He then vanished, and nobody from the band ever saw him again.