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  • 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.

  • 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.

  • 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

  • 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.

     

  • 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.

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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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