Sad Songs: They Say So Much.

I have multiple CD’s and playlists that I have made over the years that are titled, ” 😦 “. Or the literal version, “Sad Face”.

I really enjoy really sad songs. I’m not sure why. If you know me, you know that I am generally a happy, upbeat, go lucky Chick. But, when I’m feeling a bit down in the dumps sometimes, I thrive on turning up the volume on the saddest songs possible. I’m sure I’m not alone in this…right? Right???

So, if you haven’t delved into the land of sad songs that say oh, so much, you really should. Get some tissues out and have a good cry. It’s good for the soul. Like soup. But only chicken soup, not like tomato or lobster bisque….there is not a best-selling series of books called, “Minestrone for the Soul”…

I will now list some of my favorite tear-provoking tunes, in no particular order or rank, just as they come to me.

Reader’s Inside Scoop: After I listed the Top 15 Sad Songs below that I deemed most cry-worthy, I listened to each one while I wrote the descriptions. Can someone pass the Visine, another box of tissues and a stiff drink?


This Dawson pic is becoming a theme I think….

Here we go…each song listed has a link so that you can click it to listen to it…..sorry. I mean, you’re welcome.

1. This Woman’s Work- Kate Bush: Holy crap. This song is painful. From the first note this song is ripping your heart out. The words are a bit hard to understand, so I looked them up once, bad move. When you actually know what she’s saying, the song is WAY sadder. So, don’t look em up. Plus, this song was used in the movie, “She’s Having a Baby”…this just adds another whole element of sad.

2. One Last Cry- Brian McKnight:My shattered dreams and broken heart…” That is the first line, it doesn’t start getting more positive and upbeat after this, in case you were wondering…

3. Wind Beneath My Wings- Bette Midler: Whether you’ve seen the movie, “Beaches” or not….this song is sad. But, if you have seen the movie, “Beaches“, it’s WAY sadder.

4. And So It Goes- Billy Joel: Mr. Joel is such an amazingly talented song writer, singer, musician and creator of painful, heartbreaking 4 minute interludes. “My silence is my self-defense.” Ugh.

5. Sullen Girl- Fiona Apple: Fiona’s debut album, “Tidal” contained a bunch of depressing tracks and with her voice that just sounds like what heartbreak would sound like, I could’ve picked any one, but this one….I think is the best…the best, most depressing song on the album.

6. I Can’t Make You Love Me- Bonnie Raitt: Really?? Really, Bonnie Raitt?? You know what really brings the sadness to this song to a whole other level, besides the incredibly sad lyrics? The drum brush.

7. I’m Moving On- Rascal Flatts: Don’t have much to say about this one. As I’m listening to it as I type this, all I can think of is, “Are people going to see any kind of pattern in my song choices??” :/

8. The Real Thing- Kenny Loggins: When artists write songs about their kids/for their kids, it’s always really sad. What’s up with that? “I did it for you and the boys because love should teach you joy and not the imitation that your Momma and Daddy tried to show you...” I mean, it’s a good sentiment. That’s true. But still, so sad. Right?

(Another sidenote: When I looked up “The Real Thing” on YouTube, this ad for Always (You know, pantyliners) came on. It was a PSA for how saying someone does something “Like a Girl” (Runs, throws, hits…) and how that makes girls look less than….this made me laugh…and cry as well…just so you know…watch it here if you want.)

9. Goodbye My Lover- James Blunt: That first chord played on this track lets you know right away that it’s gonna be a tough one. And then his high-pitched, English voice….ouch James, ouch.

10. Sorry I Am- Ani DiFranco: Probably the least known song on this list, Ani DiFranco is one of my all time favorite singer-songwriters. Her feminist and her not selling-out to the man anthems combined with her songs about pain in every form make her one of my faves. Plus, she swears a lot and I like that. But this song, is the song I had to put on the list. Sorry, I am.

11. Tears in Heaven- Eric Clapton: Triple Ugh. I can’t say anything wise-cracky about this song. It’s too ridiculously sad. Ugh! Wish I could give Eric a hug after every time I hear this song.

12. The Living Years- Mike & The Mechanics: Okay, so not to be depressing, but this song makes me so sad because it makes me think about losing my Dad. (Sorry Sweetie…) Ugh. “I wasn’t there that morning, when my Father passed away, I didn’t get to tell him all the things I had to say...” I gotta go call my Dad.

13. I’ll Be Home for Christmas- Josh Groban: Okay, so I know this is a bit of a strange one, but have you heard it? I’m sure you have. It starts with a military Captain saying, “I want to wish a very merry Christmas to my family in Tennessee...” followed by a couple other voices of military members expressing love for their families back home that they miss being away from during Christmas on duty far away. Then, Groban sings, which is amazing of course and there are other sound bites throughout of holiday wishes from and to the troops and then it’s capped off with a little girl at the end saying, “Hi Daddy! Mommy, Bella and I are wrapping presents to put under the tree and we saved one especially for you. We miss you a lot and we hope that you can come home soon. Merry Christmas!” Shivers. Goose Bumps. Tears. Tissues. Every. Single. Time.

14. Why- Annie Lennox: Like Fiona Apple, the sincere melancholy of Annie’s voice would put any lyrics over the edge and the lyrics in this song don’t need much help.

15. There’s No Easy Way- James Ingram: Such a kind song about a man breaking a woman’s heart. But, still…it’s a break-up…and that’s sad. “I wanted her to hurt me and not treat me like a friend….but she acted like a lady till the end…oh, what a lady….”

So, there you have it. Hopefully your eyes are puffy and you’re thinking about how you have to put “Beaches” and “She’s Having a Baby” on your Netflix queue….and that you really should call your Dad, children, old friend, your ex (maybe not), anyone you know in the Military or maybe your therapist. Maybe that’s what I should do…. :/

Anyways, whoever you call or don’t call, it’s okay to listen to sad songs. They’re beautiful, make us feel like the sad things we feel are normal and everyone feels them because why else would Bonnie Raitt write that song? Why else would Mike and his Mechanics make me feel that way? We’re all feelin’ the same stuff, y’all….and sometimes we just need James Ingram or Ani DiFranco to pull it out of us.

Heart you, all you sad sacks…

sad sack







-Chick A


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