11 Sad Songs That Hurt So Good

sad songs

I love a great sad song. Most of us do. Using your singing voice (tone, phrasing, lyrics) to express a set of complex emotions that every person can relate to is a profound human experience. Sad songs touch people on a deep, personal level. That’s why we all connect with them.

Sad songs encompass a wide range of feelings-  bittersweet sentiments (my favorite), loneliness, sorrow, heartache & grief. Get your tissues out, ’cause these songs are going to get right to your squishing pink center.

Here Are 11 Beautifully Sad Songs (Sung By Great Singers)

1.)”In Love With Another Man”- Jazmine Sullivan

Ms. Jazmine Sullivan lays it down in this song as she tells her current love that she’s in love with another man. Best lyric- “I can’t explain why it’s him and not you, but at the end of the day I just don’t want to.” Ouch. 


2.)”You Don’t Know Me”- Ray Charles

Ray Charles was an incredible musician. He emotes with every single note. If he was singing in a language I didn’t understand- I’d still feel him, I’d know what he was singing about. Best lyric- “Oh I am just a friend. That’s all I’ve ever been, ’cause you don’t know me.”


3.)”Foolish Love”- Rufus Wainwright

Rufus Wainwright has one of those vocal timbres that just pierces the heart. He is a wonderful piano player as well. This song is sweet and sad in the beginning and becomes light hearted in the middle. Best lyric- “I don’t want to hold you and feel so helpless. I don’t want to smell you and loose my senses.”


4.)”Say Something”- A Great Big World & Christina Aguilera

I tear up every time I hear this song. It’s about the painful end of a great love. The video is also incredibly sad. Best lyric- “Say something, I’m giving up on you. I’ll be the one, if you want me to. Anywhere, I would’ve followed you. Say something, I’m giving up on you”


5.)”How Insensitive”- Astrud Gilberto (Jobim)

Antonio Carlos Jobim is one of the great composers of Bossa Nova. A jazz genre that came out of Brazil in the 1960’s. Astrud Gilberto (wife of Joao Gilberto- another great Bossa Nova composer) is one of the great singers of Bossa Nova. Her voice is light and pure and carries a sweet sadness. I love the entire lyric of this song, but my favorite line is- “Now he’s gone away. And I’m alone with a memory of his last look. Vague and drawn and sad. I see it still, all the heartbreak in his last look.”


6.)”Gloomy Sunday”- Billie Holiday

This is the only song in the list about grief- and it’s a dark one. Billie Holiday’s voice is haunting on this track. Best lyric- “Little white flowers will never awaken you. Not where the black coach of sorrow has taken you.” BUT WAIT- It was only a dream! “Dreaming, I was only dreaming. I wake and I find you asleep. In the deep of my heart, dear.”


7.)”I Can’t Make You Love Me”- Bonnie Raitt

No list of sad songs would be complete without this piece. With Bonnie Raitt’s incredible voice, Bruce Hornsby on keys, and the saddest heartbreak lyric ever written. Adele does a beautiful version of this song as well. Best lyric- “Here in the dark, in these final hours. I will lay down my heart and I’ll feel the power. But you won’t, no you won’t.”


8.)”I’d Rather Go Blind”- Etta James

Etta knows how to sing a sad song. This is one of my favorites that she does. It’s raw emotion- it’s the blues. Best Lyric- “Something told me it was over when I saw you and her talking. Something deep down in my soul said “Cry Girl” when I saw you and that girl walking around..”


9.) “Still Hurting”- from The Last Five Years (Jason Robert Brown)

The first time I heard this song, one of my students brought it in. I had to stop myself from tearing up (and potentially looking foolish/unprofessional). It’s about the end of a marriage and a 5 year love affair. The lyric is straight forward- it tells a sad story. All the music in this show is great. There are only two characters and they are telling their love story from different points in time, only meeting in the middle for one duet. This is the opening song of the musical, the end of the relationship from her point of view.

Best Lyric- “Jamie is sure something wonderful died. Jamie decides it’s his right to decide. Jamie’s got secrets he doesn’t confide. And I’m still hurting.”


10.)”My Man” Barbara Streisand in Funny Girl

Oh 1960’s Barbra. That voice! If you just want to hear her belt, skip to 1:20. It’s glorious. Best lyric -“For whatever my man is, I am his- forever more”


11.)”Deeper Than Crying”- Alison Krauss & Union Station

Alison Krauss has built a career on singing sad songs beautifully. Her voice is ethereal and bittersweet. I hope you enjoy this one. Best lyric- “This path is not the one I’d choose to travel.
Even as we watch what tied us unravel. And the tears fall like rain. Deeper than crying, the loving still remains.”


12.) BONUS “Almost Lover”- A Fine Frenzy

Ok, ok- I know I said 11 songs, but I just had to add this one to the list. It’s by singer/songwriter Alison Loren Sudol- also known as A Fine Frenzy. Beautiful lyric, melody and vocals. Best lyric “I cannot go to the ocean. I cannot drive the streets at night. I cannot wake up in the morning without you on my mind.”


I hope you enjoyed these songs and hopefully I introduced you to some artists and songs you didn’t know.

What is your favorite sad song?- Please leave it in the comment section!



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