10 Best Sad Breakup Songs

No matter how bitchy you say your ex was or how much you think you can drink it all away, you're most likely going to end up curled up in a fetal position some Friday night moping over your breakup, and this is where the 10 best sad breakup songs come in. Listen to these tearjerkers and revel in your misery along with Michael Jackson and Axl Rose.

  1. You've Lost That Lovin' Feelin.' The Righteous Brothers' sang about burned-out love in this classic 1965 song which, aided by Phil Spector's Wall of Sound production, became a huge hit single and one of the 10 best sad breakup songs. The song got (arguably) sadder when Tom Cruise and a bunch of drunken fighter pilots puked out its words in the 1986 movie "Top Gun."
  2. Don't Speak. Before Gwen found Gavin, she and her brother Eric Stefani penned this No Doubt tune about her breakup with bassist Tony Kanal, with whom she had a seven year relationship. The ballad, complete with flamenco-style guitar, contrasted with No Doubt's brand of shiny new-wave ska and helped the band achieve worldwide fame, keeping the former lovers stuck on the same stage and in the same hotels for many years to come.
  3. Crying. A far cry from the growling rocker heard belting out "Pretty Woman," "Crying" is classic Orbison: a deceptively complex ballad with heartfelt lyrics and lush strings arrangements. The fact that Orbison's lovelife was rife with tragedy (his wife cheated on him, remarried him and died in an automobile accident) gives this song a truly sad quality and makes it one of the 10 best sad breakup songs.
  4. She's Out Of My Life. As if singing to a pet rat in "Ben" wasn't sad enough, Michael Jackson amped up the tear factor with this classic song off his hugely successful album "Off The Wall."  According to producer Quincy Jones, MJ couldn't finish a take without crying. Now that he's gone, just try and finish listening to this song without shedding a tear for Jackson.
  5. Yesterday.  It doesn't matter that the original title for this song was "Scrambled Eggs" (McCartney heard it in a dream and those were the first words he used to fit his super memorable melody). This song's been covered more times than McDonald's sold hamburgers and stands out as not only one of the 10 best sad breakup songs, but one of the best songs altogether.
  6. Nothing Compares 2 U. Before Sinead O'Connor broke Christian hearts across America by ripping up a picture of the Pope on "Saturday Night Live", she was famous for singing one of the 10 best sad breakup songs with this song. Prince wrote it and it shows; only the Purple One could turn the words "I could eat my dinner in a fancy restaurant" into some of the saddest sounding lyrics ever.
  7. November Rain. Who knew the same man who sang the lines "Panties 'round your knees with your ass in the breeze" in Guns 'N Roses' "Anything Goes" had it in him to write one of the 10 best sad breakup songs? Axl Rose began writing "November Rain" as early as 1983 which finally came into fruition in 1992 with the help of a ton of Slash soloing, an orchestrated string arrangement and an accompanying epic video.
  8. I Will Always Love You. What's sadder than singing a song for Kevin Costner? Whitney Houston adapted this song as a single for the film "The Bodyguard" in 1992, turning an already classic Dolly Parton tune into one of the 10 best sad breakup songs. The question is: will she always love Bobby Brown?
  9. With Or Without You. Bono ditched the mullet and militant lyrics of early '80's U2 with this song about faith and spirituality. It's minimalism and distinct arpeggiated synthesizer made this song a huge hit and one of the band's signature songs.
  10. Always On My Mind.  Nobody does breakup better than country and this song, popularized by Elvis Presley and Willie Nelson, proves it. The  fact that artists as diverse as the Pet Shop Boys and B.B. King have covered it makes it certainly one of the ten best sad breakup songs.
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