The Best Breakup Songs

 

Wait for a rainy, cold, black and white movie kind of afternoon. Have a box of tissues handy, then grab a pint of Ben and Jerry’s. If you’ve got time, watch Casablanca. Now, go back in time and think about a break up - the one that wounded you the most, and then ask yourself, “what song could I absolutely not listen to during that sad time of my life?” Now you have a serious candidate for my list of  break-up songs. 

I’ve listed a number of my breakup songs below, almost exclusively from the sixties and seventies.  There are many great ones from the eighties onward, but this is my list.  There are probably some you don’t know. I’m sure I’ve missed some, and I’m sure I have several you don’t agree with. That’s ok - because music is so personal. It’s like asking who has the best barbecue - there’s a wide variance in the answers, and all of them are correct. 

To make my list, the singer needs to sound like they were  hurt. In many cases they were - so much the better.  The lyrics should also vividly describe the feeling, with the sadness of loss oozing  through every word. 

If you are looking for a near perfect example, give a listen to “How Am I Supposed To Live Without You?” by Michael Bolton. Not only does this song have great words, Bolton is singing them like it just happened to him, and he can hardly get the lyrics out.

We all know the power music has. Years ago, I got dumped, and it broke my young heart.  For the next several weeks, I had to change stations if anything Motown came on the air. It didn’t help that one of her favorite songs was a Temptations tune. Half a century later, I hear it and still think of her. 

Here’s a few of my favorites in no particular order:

Taxi - 

                    Harry Chapin

Chapin masterfully crafts a haunting narrative about two people, and the roads not taken.

Boulder to Birmingham -         

                  Emmy Lou Harris

Emmy Lou could sing pages from an accounting textbook make it sound angelic. Pair that voice with a heartfelt tribute to the death of a special person in her life, and you have something sadly spectacular.

I Can’t Make You Love Me -                                 

                  Bonnie Raitt

My personal favorite. I give it five out of five tissue boxes. Raitt recorded the song in just one take because she said it was so sad that she couldn’t recapture the emotion.

It’s still difficult for her to sing it today, although she does it in concert, saying, “It’s almost a sacred moment when you share that depth of pain with your audience…”

She’s Leaving Home - 

                      The Beatles

This one line from the song absolutely gets me: “She breaks down, and cries to her husband, Daddy, our baby’s gone.”

Adios -

                      Linda Ronstadt

In her prime, Linda Ronstadt had pipes that were unrivaled.  Add some Jimmy Webb breakup lyrics and you have a full blown pop tearjerker. “I miss the blood red sunset, but I miss you the most. Adios.  Adios.” Whoa. 

I Wish It Would Rain & 

I Could Never Love Another After Loving You -

                     The Temptations

I put these two Motown Monsters together because they were both written about a true life incident. Rodger Penzabene learned his wife had been unfaithful, and wrote the tunes to publicize the heartache she caused him. Once the songs were recorded, he committed suicide.

Tears In Heaven - 

                     Eric Clapton 

Knowing the unthinkable tragedy that fueled this song is so painful that I can barely listen to it. Clapton said this ballad to his son helped him heal. Music is indeed powerful. 

I Will Always Love You -                                       

                     Dolly Parton

                     (Or Whitney Houston)

Anyone who knows anything about Dolly knows she wrote this song to Porter Wagner when she was about to strike out on her own. Tell that to somebody who listens to this song right after being dumped. 

You’ve Lost That Loving Feeling - 

                    Righteous Brothers

    

The “blue eyed soul brothers” belt out a Phil Spector tune about a guy who trying to reboot a dying relationship. Sadly, in the girl’s mind, it’s probably already over. Erotic, and emotional -  some writers say it’s the best record ever made. 

I Fall To Pieces - 

                     Patsy Cline

When she began recording this song, Patsy Cline thought it wasn’t country enough. Wrong. On the fourth take when every man in the studio was bawling like a baby, they knew it would become a breakup song for the ages. 

Crying –

                     Roy Orbison 

Orbison’s otherworldly vocals paired with background strings gushes sadness.  Just the touch from an ex-lover is more than this guy can take. Rolling Stone ranked it 69th on their list of the 500 greatest songs of all time. It’s a top 10 breakup song.  

By The Time I Get To Phoenix -

                     Glen Campbell

Another poignant tune written by Jimmy Webb.  Frank Sinatra called it the best song of its kind ever written. Who am I to argue with Frank?  

If you haven’t heard of some of the songs, listen to them. Or drop me a message with your favorite. There are so many more. 

While  researching  this article, I asked dozens of people what their break up song would be. The best response came from my dentist who said, “Another One Bites The Dust.” 

It’s hard to argue with a man who has sharp instruments in your mouth.