My Sad Playlist

My friend Judie mentioned in one of her tweets some years ago how there are songs that would make you feel that your heart's being whipped inside a blender. Surely for me, there are songs that hurt more than others. It might be because the lines speak of a raw, familiar feeling I once had, or probably because the song itself reminds me of someone from my past already gone.

There are songs that could stop me in my tracks when I hear them. It triggers visceral responses like goosebumps, chills, or that static tingling sensation that would start from the back of my neck and could crawl to the top of my head.

There are songs like Both Sides, Now by Joni Mitchell, Fast Car by Tracy Chapman, Tears In Heaven by Eric Clapton, and Dance With My Father by Luther Vandross that are not necessarily about breakups but are just particularly sad and depressing. But since we are talking of a feeling as if your heart is being chopped and puréed, I would like to focus on the ones that are related to love (more like the lack of it).

Many people will tell you to avoid listening to these songs if you’re going through heartbreak but for me though, acknowledging the feeling is the first step to healing. A good cry can even be quite cathartic.

And since this is my personal list, you may notice that there are hardly any new, much recent songs. I grew up in a generation that enjoyed great, timeless love songs that other people may find sappy or corny. While musical taste is relative, I would like to ask you to indulge me by listening to each of the songs I included here and if you could do so while following its lyrics, then I bet you that some of the emotions expressed are truly sad. (Furthermore, keep coming back to this post as I have plans of adding more.)

I have already made a separate post earlier on one of my saddest love songs of all time by the great Lionel Richie, let me give you more.

Why Does It Hurt So Bad – Whitney Houston 


This is by far one of the saddest R&B ballads in recent memory. I prefer this live performance of Whitney at the 1996 MTV Music Awards because it showcased her vocal power and the interpretation is just so soulful (all that while sitting down). The song, written and produced by no less than Babyface, has pretty straightforward lyrics that need no deeper mincing. Stephen Holden of The New York Times said that the song is about the singer congratulating herself for breaking up with an abusive boyfriend but admits that she is still in love with him.

Le sigh.

Have You Ever? - Brandy

The words and the mid-tempo of the song (not to mention that gloomy music video) reek sadness. Written by Diane Warren and produced by the great David Foster, this power ballad speaks of unrequited love which is possibly the most overused theme in many sad songs.

I Wasn't the One (Who Said Goodbye) - Agnetha Fältskog with Peter Cetera

Years after ABBA disbanded, Agnetha released some solo albums and one of them included this single with Peter Cetera. While the former lead singer of the band Chicago has made so many collaborations with other female artists like Cher and Crystal Bernard—this one would always be the saddest of all his duets.

It tells about a couple putting the blame on the other on why the relationship collapsed even if they both obviously still feel something for each other.

I Don't Have the Heart - James Ingram

James Ingram is the king of achingly beautiful love ballads with songs like There's No Easy Way, Just Once and Where Did My Heart Go? and this one that you can call a “cruel to be kind”-anthem. Imagine being told by a guy that he loves you only that it’s not the kind of love you wanted. 
This is how being friend-zoned looks like back in the day: No ghosting, just great music.
Just When I Needed You Most - Randy VanWarmer

This song still enjoys heavy airplay on most radio stations here in the Philippines even if it was released in the late seventies. The song was written six months after a devastating breakup (the girl dumped him) so you can just imagine how real the emotions were when this was recorded.
This artist's interpretation alone, add the instrumentation, is enough to make me feel the sadness of my own feeling of loss however long ago it has been.
Somebody That I Used to Know - Gotye feat. Kimbra

The song started with the man’s point of view. He tells how he got into the relationship even if he had no plans of investing too much on it and just went through the motions. He was so used to sadness (“addicted to a certain kind of sadness”) from his previous relationship that he no longer cares if he was unhappy with his current one. The woman eventually dumped him but promises that they could still be friends. Now the guy is whining when she changes her mind and is now treating him like a stranger who didn't matter.
The following verse tells the woman’s side of the story describing the dysfunctional relationship and how she is blamed on everything that went wrong with it. Furthermore, she realized that the guy is still hung up on another woman even if he claims to have gotten over her. Realizing she was “screwed over”, she cuts him off completely instead of remaining friends with him as promised. 
The man—after all of this—even had the temerity to make it appear that he was the victim. Now, why does that sound so awfully familiar?

Against All Odds (Take a Look at Me Now) - Phil Collins

I would suggest you watch the video (from the soundtrack of the movie of the same name), not only to see how hot Jeff Bridges was pre-Lebowski/Obadiah Stane but more to see the desperation in Phil Collins' interpretation. Another slow rock inspired by a breakup, it's simply about an attempt of reconciliation against all odds.
See, some relationships are worth the try again.
What Do We Mean to Each Other - Sérgio Mendes feat. Joe Pizzulo

Sergio Mendes is a talented Brazilian songwriter and pianist known for his many collaborations. This ballad was by Joe Pizzulo, a singer who interpreted many of Mendes' more popular love songs.

This is probably one of my favorite love songs of all time, with words that are easy and uncomplicated. It is sad because it's about a feeling of not knowing where you are in a person's life. Friend? Lover? Not knowing if the other still loves you or only meant well. All the works.

Hard Habit To Break - Chicago


With lead vocals shared by Chicago frontman Peter Cetera and Bill Champlin (providing that passionate, “I’m addicted to you!”), this ballad not only sounded amazing, but the words are just heart-wrenching. 
It's tough to move on coming from a breakup with a person you've been with for so long that he or she can be likened to a habit that is so hard to give up.
Apologize - Timbaland with OneRepublic 

This song can be interpreted differently depending on who’s listening. Some say it’s about suicide perhaps because of the line, “Holding on your rope, got me ten feet off the ground” but what I think it was is that the singer was holding on to something that is already hurting/harming him.
I have a simpler explanation: it’s about being fed up with the lying, the cheating, and the hurting that saying sorry alone becomes moot.
Don't Speak - No Doubt

Reminiscent of my younger days when I sang on a band (yes, I did!) and this is the first song I covered. It was originally a love song that went through several rewrites until it ended up being a split-up song between Gwen and the band's drummer, Tony. 

Even then, I find this song sad that it cuts right deep in me even if I haven’t been in a life-altering breakup. It’s about accepting that the relationship is over and there is no need to talk about it because the parting alone is already hurtful.

No More 'I Love You's - Annie Lennox

Look past the eerie melody, theatrical vocals, the background sopranos, and the weird music video of vaudeville men in drag, this is actually a victory song of sorts only that it's sad because it was a phyrric victory. It is bittersweet because it speaks of fading love, and how the meaning of the words “I love you” seems to have disappeared with it as well. 
Annie Lennox is my queen.
One Last Cry - Brian McKnight

Everything about this song is a tearjerker. The song speaks of letting it all out in one good cry to release all the pain before finally leaving it all behind. 
“I'm gonna dry my eyes,
 Right after I had my one last cry.”

Let's Give a Little More This Time - Sérgio Mendes feat. Joe Pizzulo

I can't resist another Sérgio Mendes and Joe Pizzulo collab on the list. This one may seem to be a happy, second chances song, but I remember reading somewhere (or watching an interview) where they said this is actually a sad one. I couldn't agree more because there's some desperation in the plea to make the relationship work and not make the same mistakes as before.

Crying in the Rain - A-ha

A more somber and gloomy take on the 1960s Everly Brothers original by the '80s Norwegian band A-ha, who had given us the classic synth-pop Take On Me. 

Crying has always been viewed as a show of weakness especially among men. This is why in this case, to hide it, the singer waits for the rain so he could hide the tears.

Even Now - Barry Manilow

This is, by far, one of the most UNFAIR songs there is. If you listen to the lyrics, the situation being described is especially tough to the singer, unfair to the person this song is being sung to, and most of all, unkind and inconsiderate to whoever it is currently in a relationship with the one singing it. 
After The Love Has Gone - Earth, Wind and Fire

I was choosing between this and another EWF song that is equally sad (which they say is actually the sequel song), but I guess this is sadder because it speaks about a relationship that has gone bad and eventually ended. The singer struggles in understanding where things could have gone wrong. The part, “What used to be right is wrong, can love once lost be found?” strikes a chord in me even then and more so now. 
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There you have it. Some of the saddest songs on my playlist. Judie wasn’t lying, it does feel like my heart’s inside a blender every time I hear these even if no doubt that they are all great songs. 

Feel free to share yours on the comment box!