Sad Blues Songs, The Saddest Ever

The blues were born from hard times, so it’s a long shot to find a happy one. I’ll tell you now, it was hard to narrow this list down to such a small number of sad blues songs, but I managed it. Here are the best.

1. “Born Under a Bad Sign” by Albert King

“Born Under a Bad Sign” by Albert King

Song Year: 1967

“Born Under a Bad Sign” encapsulates all you need to know about blues music. The narrator has had a miserable existence since he took his first breath.

He’s only ever had bad luck, and he’s never been able to get on his feet in life. He never even learned to read. In the end, he understands that even if he finds a woman to love, she’ll be the death of him.

2. “Someday After A While (You’ll Be Sorry)” by Freddie King

Song Year: 1963

There’s something truly sad watching someone go through sour grapes emotions. Freddie King does just that in “Someday After A While (You’ll Be Sorry)” watching his girl walk away. He doesn’t go so far as to say he never loved her in the first place, but that whole idea of you’ll-regret-this-on-the-future has roots in the same emotional place.

3. “Call It Stormy Monday (But Tuesday is Just as Bad)” by T-Bone Walker

Song Year: 1947

While T-Bone Walker isn’t exactly a household name anymore, before the second world war, he was an innovative bluesman who was one of the first to use an electric guitar.

“Call It Stormy Monday (But Tuesday is Just as Bad)” recounts a sad week in the life of a lonely man who just wants his woman to come back.

4. “Death Letter Blues” by Son House

“Death Letter Blues” by Son House

Song Year: 1965

Before email we got bad news via snail-mail. In “Death Letter Blues,” Son House’s narrator gets a letter telling him of the death of his woman.

The song, built on a simple blues chord progression, relies on the power of the lyrics and Son House’s anguished delivery. Listening to him sing it, you’d think it was a true story.

5. “Piece Of My Heart” by Big Brother and the Holding Company

Song Year: 1968

One of Janis Joplin’s signature songs, “Piece of My Heart” was first recorded in 1967 by Erma Franklin, but as the voice of Big Brother, Joplin made it her own.

The lyrics reveal a woman who will do anything to keep the man she’s losing. There’s a heartbreaking undertone that has Joplin seeming to believe that if she just keeps giving the jerk enough chances, everything will be okay. But it won’t be.

6. “Dark Was the Night, Cold Was the Ground” by Blind Willie Johnson

Song Year: 1927

Loosely based on an 18th-century hymn, Blind Willie Johnson’s “Dark Was the Night, Cold Was the Ground” is one of those songs that doesn’t need words. His bottleneck slide-guitar work, along with the mournful moaning over it, make for an almost oppressive sadness emanating from your speakers or your AirPods.

7. “Worried Dream” by B.B. King

Song Year: 1968

When you have one of those realistic dreams, sometimes it’s hard to shake it in the morning. That’s the case in B.B. King’s  “Worried Dream.” He has a nightmare that his woman is running around on him, and it’s disturbing enough that he wakes up in tears.

The worst part is that he demands that she tell him it was just a dream, but he gets no response, which says it all.

8. “The Sky Is Crying” by Elmore James

“The Sky Is Crying” by Elmore James

Song Year: 1960

Sometimes people make pejorative references to the blues along the lines of, “Every song is ‘My baby done left me.’” While that’s an oversimplification, it’s the gist of Elmore James’ “The Sky is Crying.”

The narrator has realized his girl has gone away, and the sorrow is so overwhelming that he can’t imagine any other reason for the water falling from the sky. Surely the entire world is as sad as he is.

9. “Five Long Years” by Eddie Boyd

Song Year: 1952

When a man works a hard job to provide for his woman, he’s understandably going to be upset when she leaves him. Eddie Boyd penned “Five Long Years” and depicted a man whose pain has turned him bitter.

The narrator decides that from now on, he’ll only go with women who work while he stays home. Good luck.

10. “Double Trouble” by Otis Rush

Song Year: 1959

In This Is Spinal Tap, we learned that D minor is the saddest of all keys. Put a blues song in that key, and you’ve got the makings for true musical sorrow.

“Double Trouble” finds Otis Rush bemoaning his life and its unfairness. The narrator has nothing and the world laughs at him for it, and the existence of rich people when he’s destitute is just salt in the wound.

11. “I Can’t Make You Love Me” by Bonnie Raitt

Song Year: 1991

Bonnie Raitt’s “I Can’t Make You Love Me” recounts the end of a relationship and a situation many of us have experienced at least once: one person in the partnership is in love, but the other one isn’t. The futility of trying to make things work when they’re obviously doomed drips from Raitt’s voice in this ridiculously sad piece of music.

12. “Wild Horses” by The Rolling Stones

Song Year: 1971

One of the gentler Rolling Stones songs, “Wild Horses” paints a picture of a man who has been hurt terribly by his beloved. But no matter what she’s put the narrator through, he still loves her. There isn’t any pain she could put him through that would make him give up on her. Anyone who’s loved someone who can’t get out of their own way can identify with that sentiment.

13. “House of the Rising Sun” by The Animals

“House of the Rising Sun” by The Animals

Song Year: 1964

The Animals had a big hit with “House of the Rising Sun,” but tons of people have covered it, and evidence suggests it may have been written in the 1800s.

It tells the story of the fall of a gambler whose life went to pieces in New Orleans. The narrator is the gambler’s son, and he follows in his father’s footsteps. The whole thing is a cautionary tale, and those are always sad since the teller of the tale has walked a terrible path.

14. “Marie” by Townes Van Zandt

Song Year: 1994

Townes Van Zandt was one of those songwriters who was immensely talented but equally tormented by his own personal demons. Though “Marie” isn’t autobiographical, the abject despair on display in this story of a man down on his luck are made harder to bear when you know about Van Zandt’s struggles with various addictions.

As if the sadness wasn’t tough enough, what with unemployment and the death of family members, the narrator reveals at the end that Marie, pregnant with a son, died in her sleep.

15. “Crying” by Don McLean

“Crying” by Don McLean

Song Year: 1980

Roy Orbison’s 1961 recording of “Crying” was a big hit and became perhaps his signature song. But his soaring falsetto lent something vaguely hopeful to the song.

That is not the case with Don McLean’s version. His more pensive delivery packs a bigger emotional punch.

Sad Blues Songs, Final Thoughts

Arising from spirituals and work songs, blues music represents America’s contribution to the music of the world. There’s something comforting in sharing your pain with someone singing about the same emotions you’re dealing with. These 15 sad blues songs depict a range of types of sadness and despair, which is what we want from good blues music.

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