10 Saddest Break Up Songs

The best break up songs convey the world-ending sadness one feels when true love ends; the 10 saddest break up songs are perfect examples of that old adage that happy people don't make great art. The saddest break up songs cross genres from rock and roll to country to the coldest, gloomiest post-punk. Here are the saddest break up songs in popular music history.

  1. "Alone Again Or" by Love – The opening song to a classic sad album, "Forever Changes," Love's most enduring song gallops along at a frenetic pace, but its minor key and off-kilter harmonies convey the sadness of the lyrics. "Alone Again Or" tops the list of the saddest break up songs.
  2. "Love Will Tear Us Apart" by Joy Division – This dark, danceable tune is also one of the saddest break up songs of all time. The chorus, simply, "Love…love will tear us apart, again" tells the whole story.
  3. "Ever Fallen in Love" by the Buzzcocks – Punk's greatest doomed-love song is the Buzzcocks' most enduring hit. The protagonist feels like dirt, is hurt, because he's fallen in love with someone he shouldn't have fallen in love with.
  4. "So Sad About Us" by the Who – The Who weren't known for love songs, but this entry on the saddest break up songs from their power-pop period is one of their most underrated singles. "Apologies mean nothing when the damage is done," say Townshend's lyrics on the bridge. Indeed.
  5. "Don't Think Twice It's All Right" by Bob Dylan – One of Dylan's earliest, most well-known songs is one of the saddest break up songs because the sadness is masked by anger. It is bitter and brilliant.
  6. "Can't Stand Losing You" by the Police – What sounds like a bouncy pop nugget is actually one of the saddest break up songs of all time, with Sting contemplating suicide after losing the titular "you." Few know this enduring hit is as dark as it is.
  7. "Alison" by Elvis Costello – Elvis Costello's first hit song is romantic until one listens to the lyrics. Bitterness over betrayal has never sounded so sadly beautiful.
  8. "Heartbreak Hotel" by Elvis Presley – One of the saddest break up songs is carried entirely by Elvis' beautiful voice. It is full of heartache.
  9. "Crazy" by Patsy Cline – Written by Willie Nelson, "Crazy" became a hall of fame sad break up song in the hands of Patsy Cline. It is so beautiful, it almost makes sadness seem wonderful.
  10. "True Love Waits" by Radiohead – This rare Radiohead song is Thom Yorke's saddest break up song. It is simple and beautiful, a perfect capper to the list of saddest break up songs.
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