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  • Jeremy on Random Depressing Stories Behind Some Of Most Popular Songs In Modern History

    (#1) Jeremy

    • Pearl Jam

    While Pearl Jam's "Jeremy" is focused on a student taking his own life in front of his class in 1991 in Texas.

  • The Way on Random Depressing Stories Behind Some Of Most Popular Songs In Modern History

    (#2) The Way

    • Fastball

    Pop band Fastball's only hit, "The Way," tells a romanticized version of a real story - about two elderly 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.

    The couple was found deceased two weeks later at the bottom of a ravine near Hot Springs, AR, hundreds of miles away from where they intended to go.

  • Joy Division - 'Love Will Tear Us Apart' on Random Depressing Stories Behind Some Of Most Popular Songs In Modern History

    (#3) Joy Division - 'Love Will Tear Us Apart'

    Deeply-troubled Joy Division lead singer Ian Curtis wrote the band’s only real hit about the tempestuous relationship he had with his wife, Deborah. It also reflected his state of mind in general - and if the song did not communicate how depressed Curtis was, the fact that he took his own life just a few weeks before the track was due to be released as a single.

  • Circus on Random Depressing Stories Behind Some Of Most Popular Songs In Modern History

    (#4) Circus

    • Eric Clapton

    While "Tears in Heaven" is famously about the passing of Eric Clapton's young son, Conor, in 1991, it is not the only song about this subject matter. Another track, "Circus," from his 1997 album Pilgrim, was also written by Clapton about the tragic accident and is just as sad and forlorn.

    The song is about the last time Clapton saw Conor, the night before the incident, when Clapton took him to the circus.

  • Blondie - 'One Way or Another' on Random Depressing Stories Behind Some Of Most Popular Songs In Modern History

    (#5) Blondie - 'One Way or Another'

    One of Blondie’s many hits, the poppy and up-tempo "One Way or Another," actually stems from a harrowing experience for lead singer Debbie Harry - being stalked by an ex-boyfriend. A closer examination finds a number of incredibly creepy lines about following, watching, and cataloging Harry's activities.

  • The Needle and the Damage Done on Random Depressing Stories Behind Some Of Most Popular Songs In Modern History

    (#6) The Needle and the Damage Done

    • Neil Young

    While obviously about substance abuse, it's less well known that Neil Young wrote this song about a specific person. Included on the 1972 album Harvest, "The Needle and the Damage Done" eulogizes the 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 Los Angeles so he could take care of his addiction. Whitten used the money to get high and suffered a subsequent overdose. 

  • Pink Floyd - 'Shine on You Crazy Diamond' on Random Depressing Stories Behind Some Of Most Popular Songs In Modern History

    (#7) Pink Floyd - 'Shine on You Crazy Diamond'

    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 where the band was recording the song about him. At first, nobody recognized Barrett, who had gained weight and shaved his head since being ousted from the group years earlier. Before his death, he would only be seen by a band member once more. Roger Waters saw him buying sweets in London a couple of years later, but the two reportedly did not speak.

  • I Wish It Would Rain on Random Depressing Stories Behind Some Of Most Popular Songs In Modern History

    (#8) I Wish It Would Rain

    • The Temptations

    Motown staff lyricist Rodger Penzabene wrote this heartbreaking ballad for The Temptations, and singer David Ruffin's impassioned vocals drove it to the Top 5 on Billboard's R&B chart. But while Ruffin's pain was a performance, Penzabene's was real - he reportedly wrote the song in a fit of anguish after learning his wife was cheating on him.

  • Nena - '99 Red Balloons' on Random Depressing Stories Behind Some Of Most Popular Songs In Modern History

    (#9) Nena - '99 Red Balloons'

    While German band Nena had a massive hit with the poptastic "99 Luftballoons/Red Balloons," few people stopped dancing long enough to figure out that the song was actually about the tensions between West and East Germany during the Cold War

  • The Wreck of the Edmund Fitzgerald on Random Depressing Stories Behind Some Of Most Popular Songs In Modern History

    (#10) The Wreck of the Edmund Fitzgerald

    • Gordon Lightfoot

    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.

  • Gimme Shelter on Random Depressing Stories Behind Some Of Most Popular Songs In Modern History

    (#11) Gimme Shelter

    • The Rolling Stones

    A staple of Martin Scorsese’s filmography, "Gimme Shelter" started as commentary from Keith Richards about the state of the world in 1968, specifically the chaos of the Vietnam War. It took on a life of its own after an attack on a fan at the band's disastrous free show at Altamont.

    Less well known is the fact that singer Merry Clayton, who provided the soaring counter-point to Mick Jagger on the song, suffered a miscarriage shortly after the album sessions - ostensibly from the intensity of recording the song.

  • Semi-Charmed Life on Random Depressing Stories Behind Some Of Most Popular Songs In Modern History

    (#12) Semi-Charmed Life

    • Third Eye Blind

    Third Eye Blind’s biggest hit, "Semi-Charmed Life," is both extremely upbeat and catchy, and brutally depressing. Written about the challenges of addiction and using other vices to reach an equivalent high, its impact was somewhat blunted by the fact that all of the actual references to substances were bleeped or back-masked in the radio edit of the song.

  • Sister on Random Depressing Stories Behind Some Of Most Popular Songs In Modern History

    (#13) Sister

    • Prince

    Buried on Prince's 1980 album Dirty Mind is "Sister," a short funk track about seducing one's… well, you know. Prince fans thought the track was pure fantasy, but when more biographical details about the Purple One started to come out, the song took on a weird, dark meaning.

    It seems that a 16-year-old Prince spent some time living with his half-sister, who was 32. 

  • Van Halen - 'Jump' on Random Depressing Stories Behind Some Of Most Popular Songs In Modern History

    (#14) Van Halen - 'Jump'

    Van Halen's 1984 hit wasn't about a metaphorical jump, but someone actually threatening to take their own life in this way. David Lee Roth claimed he was watching the news and saw a live report about a man threatening to jump off the Arco Tower in Los Angeles.

    The incident struck Roth with a fit of inspiration and he wrote the lyrics, turning it into a huge hit.

  • Shiny Happy People on Random Depressing Stories Behind Some Of Most Popular Songs In Modern History

    (#15) Shiny Happy People

    • R.E.M.

    While seemingly a jokey and slight REM song about people going through life with no cares, "Shiny Happy People" is thought to have drawn its initial inspiration from a fairly dark place. The title phrase was the translation of a propaganda poster from China's Mao era that read "shiny happy people holding hands." The song was written and recorded after the Tiananmen Square incident in Beijing, an event that weighed heavily on the band.

     

  • Detroit Rock City on Random Depressing Stories Behind Some Of Most Popular Songs In Modern History

    (#16) Detroit Rock City

    • Kiss

    One doesn’t normally associate KISS with harrowing personal trauma, but guitarist Paul Stanley had that in mind when he wrote "Detroit Rock City." Stanley wrote the song about a KISS fan who was felled in a car crash after he went to see the band perform. 

     

  • Born in the U.S.A. on Random Depressing Stories Behind Some Of Most Popular Songs In Modern History

    (#17) Born in the U.S.A.

    • Bruce Springsteen, E Street Band, Bruce Springsteen & The E Street Band

    One of the most misinterpreted songs in the Bruce Springsteen canon, "Born in the USA" isn't a cherry anthem of patriotic flag-waving, but a scathing indictment of the treatment of Vietnam veterans.

  • Listen to Her Heart on Random Depressing Stories Behind Some Of Most Popular Songs In Modern History

    (#18) Listen to Her Heart

    • Tom Petty and the Heartbreakers

    Who was the "he" mentioned in the song who was going to take Tom Petty's lady away with promises of the fast life? Apparently, it was Ike Turner, who hit on Petty's wife, Jane, at a party.

    Jane rebuffed Turner's advances, but Tom saw the whole thing go down and wrote the song in response.

  • Ladies & Gentlemen, We Are Floating In Space on Random Depressing Stories Behind Some Of Most Popular Songs In Modern History

    (#19) Ladies & Gentlemen, We Are Floating In Space

    • Spiritualized

    Spiritualized's mastermind/lead singer Jason Pierce was in a long-term relationship with the band's keyboard player Kate Radley. Sometime in 1995 or 1996, though, she secretly married The Verve lead singer Richard Ashcroft - while she was still ostensibly in a relationship with Pierce. Needless to say, this was crushing to him, and he wrote the title track of this deeply sad record about her.

     

  • Maps on Random Depressing Stories Behind Some Of Most Popular Songs In Modern History

    (#20) Maps

    • Yeah Yeah Yeahs

    With its crushing backbeat and impassioned vocals from Karen O., the Yeah Yeah Yeahs' "Maps" elevated them from being one of many New York indie groups to playing arenas. But what did it have to do with cartography? Nothing, as it turns out. According to the singer, "Maps" was actually an acronym for "My Angus Please Stay," and the song is a plea to Karen's boyfriend, singer Angus Andrew, not to break up with her.

    It didn't work, and the couple eventually broke up.

  • Bob Dylan - 'Sara' on Random Depressing Stories Behind Some Of Most Popular Songs In Modern History

    (#21) Bob Dylan - 'Sara'

    Much of Bob Dylan's material in the '70s was inspired by the difficult relationship he had with his wife Sara. This was especially poignant in the 1975 album Blood on the Tracks, which is essentially a blow-by-blow account of their breakup. But a year later, Dylan pulled out all the stops to win Sara back, writing this harrowing ballad as the final track of his album Desire.

    The song was more personal and focused than almost anything Dylan ever wrote but it was not enough to win Sara back. They divorced in 1977.

  • Bob Marley - 'I Shot the Sheriff' on Random Depressing Stories Behind Some Of Most Popular Songs In Modern History

    (#22) Bob Marley - 'I Shot the Sheriff'

    According to an ex-girlfriend of Bob Marley, "I Shot the Sheriff" had nothing to do with terminating a lawman, but with Marley's disdain for contraception. Apparently, Esther Anderson was taking birth control pills, which Marley found to be sinful. So he wrote a song turning the doctor who prescribed the pills into an errant lawman in need of justice.

    Marley himself never claimed this about the song, but at the very least this information gives the listener an interesting perspective on the song. 

  • Escape (The Pina Colada Song) on Random Depressing Stories Behind Some Of Most Popular Songs In Modern History

    (#23) Escape (The Pina Colada Song)

    • Rupert Holmes

    Rupert Holmes’s cheery song about tropical drinks and getting caught in the rain actually has a dark undercurrent: it's about a couple cheating on each other. Holmes's song describes a man who uses a personal ad to find a woman with whom to cheat on his wife. When he goes to meet the woman, he finds out that she is actually his wife. 

    The song was a monster hit, but Holmes could never repeat its success.

  • The Kinks - 'Lola' on Random Depressing Stories Behind Some Of Most Popular Songs In Modern History

    (#24) The Kinks - 'Lola'

    One of the biggest hits for the Kinks, "Lola" was inspired not by a fictional character, but by songwriter Ray Davies finding out that the band's manager, Robert Wace, had unknowingly spent an evening with a transgender individual in the midst of transition. The song was censored by many radio stations who were uncomfortable with the song's subject, which was considered taboo for the time. 

     

  • Bachman-Turner Overdrive - 'You Ain't Seen Nothin' Yet' on Random Depressing Stories Behind Some Of Most Popular Songs In Modern History

    (#25) Bachman-Turner Overdrive - 'You Ain't Seen Nothin' Yet'

    A case of a seemingly tossed off song becoming a monster hit, Bachman-Turner Overdrive's "You Ain't Seen Nothin' Yet" started its life as a rehearsal piece that for which Randy Bachman had only written temporary lyrics. The trademark stutter in the song was a way for Randy to tweak his brother Gary's stutter.

    It was never meant for public consumption, but was included on the band's 1974 album Not Fragile because they needed one more track.

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About This Tool

Sad songs don't have to be based on real tragedy. But some hits speak the truth about the worst heartbreak things in life. Some of the most iconic songs of all time came about the real experiences of artists or bands. Breakups, divorce, friendships, betrayals, and mental health struggles are just a few of the life experiences that have inspired some of the most famous songs.

People rarely have a chance to know the intention of the songwriter or music artists. This page collates 14 entries, there is a collection of depressing stories behind some of the most popular songs in modern history. You can find more information.

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