The 3 Saddest Breakup Songs

4 years ago by in Audio, Quotes

Everyone knows that the primary purpose of pop music is to rock out when you’ve been dumped by some jerkbag (or multiple jerkbags, or the same jerkbag multiple times – music is flexible like that).  As therapeutic as it is to sing “We are never never never getting back together!” as you cruise down the highway in your ’94 Civic, we can only assume it’s even more cathartic for the songwriters who spun lyrical gold from the dross of their failed relationships.

So to honor those poor, broken-hearted rockstars, here’s a list of the most gut-wrenching breakup songs:

The 3 Saddest Breakup Songs:

1. “Don’t Speak” by No Doubt

“Don’t Speak” was penned by lead singer (and later solo star) Gwen Stefani after a nasty split with No Doubt bassist Tony Kanal. The couple dated for 7 years, so Tony’s dumping stung, to say the least.  To add insult to injury, the exes had to continue working and touring together.  As Kanal said:

We were on tour for Tragic Kingdom for 28 months.  We were going through the breakup, and in every interview we were talking about it so we were opening this wound on an hourly basis.  It was so brutal but I don’t know how we made it through.

Gwen responded with these lyrics:

I really feel 

That I’m losing my best friend 

I can’t believe

This could be the end 

It looks as though you’re letting go 

And if it’s real 

Well I don’t want to know

As bummed as Gwen must have been, “Don’t Speak” became No Doubt’s most successful international single and was nominated for Song Of The Year at the 1998 Grammys.  Gwen definitely saw the silver lining:

Before, I was really passive, all I cared about was being in love with my boyfriend.  I didn’t have any creative power, nothing. I don’t know that person any more. But I’d been really bad at school and didn’t know what I would do, I just sang in my brother’s band.  But after the breakup I just started writing all these songs and suddenly I was: ‘Oh I think I’m really good at this!’

Stefani and Kanal are now friends, both happily married to other people (Kanal to actress Erin Lokitz and Stefani to rocker Gavin Rossdale.) Stefani has since written another song inspired by Kanal, the much gentler “Cool”:

And after all the obstacles

It’s good to see you now with someone else

And it’s such a miracle that you and me are still good friends

After all that we’ve been through

I know we’re cool

We used to think it was impossible

Now you call me by my new last name

Memories seem like so long ago

Time always kills the pain

2. “Ain’t No Sunshine When She’s Gone” by Bill Withers

“Ain’t No Sunshine” has become one of the most-covered songs of all time because everyone has felt the icy chill that pours over you when your loved one is gone.

“Ain’t No Sunshine” was originally released in 1971 on Wither’s album Just As I Am.  Withers was actually inspired by a 1962 film called Days Of Wine And Roses, not any particular relationship of his own.  Speaking of the film’s main characters, he said:

They were both alcoholics who were alternately weak and strong. It’s like going back for seconds on rat poison. Sometimes you miss things that weren’t particularly good for you. It’s just something that crossed my mind from watching that movie, and probably something else that happened in my life that I’m not aware of.

Withers originally intended to write an extra verse, using the phrase “I know” repeated 26 times as a stopgap, but his musical peers convinced him to leave the song as it was.

“Ain’t No Sunshine” became a huge hit, taking Withers from his job as a factory technician making toilet seats for 747s to a successful full-time musician.

On a side note, “Ain’t No Sunshine” is used in one of my favorite movie montages of all time in Notting Hill.  You can check it out here:

3. “Someone Like You” by Adele

Taylor Swift is probably the only person more famous than Adele for singing about exes.  One of Adele’s former paramours famously tried to sue her for taking the material for her first album from their failed breakup.  Her sophomore effort 21 drew from her relationship with Alex Sturrock, the photographer on her 2009 tour.

The haunting, piano-accompanied single “Someone Like You” became wildly successful, making Adele the first female British singer to have two #1 hits from the same album on the Billboard Hot 100.  The single went platinum five times in the US, and artists like Katy Perry and Taio Cruz identified so strongly with the lyrics that they performed their own covers.

Adele said:

When I was writing it I was feeling pretty miserable and pretty lonely, which I guess kind of contradicts “Rolling in the Deep”. Whereas that was about me saying, ‘I’m going to be fine without you’, this is me on my knees really…I can imagine being about 40 and looking for him again, only to turn up and find that he’s settled with a beautiful wife and beautiful kids and he’s completely happy… and I’m still on my own. The song’s about that and I’m scared at the thought of that.

Adele and Sturrock dated 18 months:

We were so intense I thought we would get married. But that was something he never wanted… So when I found out he does want that with someone else, it was just the horrible-est feeling ever. But after I wrote it, I felt more at peace. It set me free… I didn’t think it would resonate… with the world! I’m never gonna write a song like that again. I think that’s the song I’ll be known for…I wrote that song on the end of my bed. I had a cold. I was waiting for my bath to run. I’d found out that he’d got engaged to someone else.

Rarely has the pain of a breakup been expressed with such purity or such poetic lyrics.  Adele is right – “Someone Like You” is the song she’ll be known for.

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