The 25 Saddest Songs of All Time

Whether they make you sad over a break up, the end of an era, the loss of friends, or just the pure melodic genius of the artist, every song on this list is a bonafied tear-jerker. From classical, to country, this list is all encompassing! So get out that box of tissues and prepare yourself for a good cry.

25. Free as a Bird by The Beatles

Originally recorded by John Lennon on his own, the other Beatles re-recorded this song in the 90’s, releasing it as part of their Beatles Anthology. Light on the lyrics and heavy on the melody, the song speaks on the subject of the band’s break-up, asking the questions every Beatles fan was left with after the separation, “Whatever happened to the life that we once knew? Can we really live without each other?”.

24. See You Soon by Coldplay

While there aren’t any overwhelmingly sad lyrical moments in this song, it’s really the complete package that gets the listener. See You Soon just talks about taking what life is throwing at you, and moving on the best way that you can. Whether you interpret Chris Martin’s words as a break up, or maybe just another tough moment in life, there is no doubt that sometimes, a huge dose of reality can be one of the most emotional things to hear.

23. Black Balloon by Goo Goo Dolls

According to Johnny Rzeznik, “Black Balloon” tells the story of a young woman, who eventually dies from a heroin addiction, inspite of her lovers desperate attempts to save her. Speculation has circulated for years that the song actually told the story of bassist Robby Takac’s ex-wife, who died from a heroin overdose, but the band has never confirmed the suspicions.

22. Now and Forever by Carole King

Like so many other songs on this list, Carole King’s hit, Now and Forever, tells the story of a loved one lost. Often used to remember friends or family who don’t get to spend enough time on this earth, King’s lyrics “We had a moment, just one moment. That will last beyond a dream, beyond a lifetime. We are the lucky ones, some people never get to do, all we got to do….” can melt the strongest of hearts, which is why it made our list.

21. 1916 by Motorhead

Released in 1991, this rock ballad tells the story of a World War I soldier. Singer Lemmy’s voice, lightly accompanied, creates a haunting effect, perfect for the telling of such a sad story. Very few songs have ever taken such a literal and honest approach from a soldier’s point of view, which makes this not only a tear jerker, but truly unique.

20. Lost Cause by Beck

One of the best break-up songs of all times, Lost Cause tells the story of a man trying to cope with lost love. Like so many other “sad” songs, the true desperation is found in the realistic aspect of this song. Everyone has reached that point in a relationship where they’re “tired of fighting for a lost cause”, but hearing it played out in a song certainly doesn’t lessen the blow.

19. Naked as we Came by Iron and Wine

Who knew a concept as simple as birth and death could become such a beautifully depressing song. This song tells the story of a couple, contemplating leaving life exactly the way the entered it, with nothing. The real tear-jerker moment comes with the realization that one lover will die before the other, and the songs says, “I lay smiling like our sleeping children, One of us will die inside these arms.” I guess if you have to go, that isn’t a bad way to do it.

18. Luka by Suzanne Vega

Paired with its strange upbeat melody and epicly sad story of child abuse, Luka by Suzanne Vega is not only one of the saddest songs, but one of the strangest. It tells the story of a little boy, Luka, who is suffering from child abuse, and the way he deals with it. One of the earliest songs to deal with such a subject, one critic claimed the ‘happy’ music is a metaphorical denial, making this seem beautiful and serene while discussing something terrible and devastating. It is a wonderful use of tune as a metaphor for how many abuse victims also deny their abuse, and is a profound classic”.

17. The Biggest Lie by Elliot Smith

Telling the story of a man trying to deal with a break up, The Biggest Lie is a true reflection of Elliot Smith’s real life. In 2003, after getting into a fight with his girlfriend, Smith committed suicide by stabbing himself in the heart. As a listener, when Smith sings the final verse, saying “Oh we’re so very precious, you and I. And everything that you do makes me want to die”, it hits just a little too close to home.

16. The Freshman by Verve Pipe

This 1997 hit tells the story of a young couple, and the suicide of the girl after their choice to have an abortion. Based on frontman’s Brian Vander Ark personal experience with abortion, the song took a little poetic licesne, since Vander Ark’s real-life girlfriend didn’t really commit suicide. Nonetheless, it tells a story that a lot of people can relate to, which combined with Vander Ark’s raspy-emotional voice makes it so damn sad.

15. Black by Pearl Jam

Written by Pearl Jam guitarist Stone Gossard in 1990, Black became one of the most well known Pearl Jam ballads. Although the song was never released, fans related to it on a deeply personal level. When Eddie Vedder sings the immortal words, “I know someday you’ll have a beautiful life, I know you’ll be a sun in somebody else’s sky. But why, why, why can’t it be, can’t it be mine”, broken hearts around the world united, cementing this as one of the saddest songs of all times.

14. I Will Follow You Into the Dark by Death Cab for Cutie

When Death Cab front man Ben Gibbard wrote “I Will Follow You Into the Dark”, he wasn’t really familiar with losing loved ones. Gibbard was at a point in his life where he began to wonder about growing older and dying, and the experience that goes along with that. About the piece, Gibbard said, “It’s just this idea that what if somebody dies and we’re just floating, just stumbling around in infinite darkness, and I’m just trying to find some kind of spiritual kind of peace with myself, and the world.”

13. Today has been Okay by Emiliana Torrini

Telling three different stories throughout the arc of the song, Icelandic singer Emiliana Torrini’s haunting voice and melodies add to the mood of this song. One story tells of a break-up, and how a woman is fighting just to get through her day. The second verse tells the story of a family conflicted and dealing with change. The third and final verse tells the story of a person who has presumably met death, and the singer’s attempt to deal with that loss. Although this song is meant to be about coping, it can put a tear in the eye of most!

12. Both Sides Now by Joni Mitchell

Ranked 170 by Rolling Stone on the 500 Greatest Songs of All Times, Joni Mitchell’s “Both Sides Now” tells a story any listener can relate to. The song shows listeners that the only way to experience life and love is to actually go out there and live it. There are parts of life that are fun and happy, but there are just as many that are sad and upsetting. And nobody tells that story better than Ms. Mitchell.

11. I’ll Cover You (Reprise) from RENT

Featured in the award winning musical RENT, I’ll Cover You (Reprise) occurs in the musical at a point when one of the main character’s has just lost his partner and lover. Composed and written by Jonathan Larson, the song shares the torture of losing a person you love. Originally performed by ‘Law and Order’ star Jesse L. Martin, the pain and exhaustion of such an experience is actually audible in his amazing performance, bring this song in on our list at number 15.

10. Adagio for Strings by Samuel Barber

The only fully instrumental piece on our list, Adagio for Strings has been analyzed as the saddest piece of music ever written. Composed by Samuel Barber and made famous when used in the 1970’s hit film, Platoon, Adagio for Strings can envoke saddness in most people, frequently reducing people to tears!

9. Whiskey Lullaby by Brad Paisley ft. Allison Kraus

Recorded by Brad Paisley and Allison Kraus in 2003, Whiskey Lullaby tells the story of a couple who separate, and eventually drink themselves to death. You know a song will be sad when it combines endlessly star-crossed lovers and chronic drinking. The raw pain and emotion are captured in the beautiful words of the chorus, “He put that bottle to his head and pulled the trigger, and finally drank away her memory…We found him with his face down in the pillow, with a note that said I’ll love her till I die”.

8. Pink Moon by Nick Drake

While there may not be anything obviously sad about Nick Drake’s song, Pink Moon, knowing any kind of story behind it might change your opinion. Drake, an English singer/songwriter, was one of the most influential British song-writers of the 20th century. Drake, who died at the age of 26 from a prescription drug overdose, battled insomnia and depression for most of his life, which was often reflected, either melodically or lyrically in his music. Late Hollywood star Heath Ledger held Drake in high esteem, saying, “I was obsessed with his story and his music and I pursued it for a while and still have hopes to kind of tell his story one day”. Ledger died in 2008 at age 28, also from an overdose.

7. Concrete Angel by Martina McBride

Telling the story of a little girl stuck in an abusive home, Concrete Angel is one of those songs that just sneaks up on you. The beautiful melody and and entrancing nature of Martina McBride’s voice draw you into this very sad story. This song, which was written to help raise awareness about child abuse, tears your heart out at the end, with the little girl eventually dying after her mother’s drunken rage. There isn’t more that really needs to be said about this song, it’s truly one of the most depressing songs to listen to.

6. One Moment More by Mindy Smith

Written for her mother, who was dying from cancer, Mindy Smith sings the words everyone wants to say when losing someone they care about. Her simple voice and beautiful melody allow you to hear the desperation and love in this amazing song. Every time she sings, “Oh, please don’t go, Let me have you just one moment more”, you can almost feel your heart breaking. Mindy has gone without a lot of recognition as an artist, but no one can dispute that this is one of the saddest songs to make our list.

5. Elizabeth on the Bathroom Floor by Eels

“Laying on the bathroom floor, Kitty licks my cheek once more. And I could try, but waking up is harder when you wanna die”. When a song starts out like that, you know it’s gonna be a depressing one. Performed by eels, Elizabeth on the Bathroom Floor was written in response to the suicide of front man Mark Oliver Everett’s sister. Talk about heavy material. Even without the back-story, this song is achingly sad, which is why it comes in on our list at # 5.

4. Brick by Ben Folds Five

Deemed one of the “saddest songs in the happiest keys” (D Major), Ben Folds Five’s “Brick” tells the story of a young couple getting an abortion. The song, based on Fold’s personal experience, was met with controversy, but the artist eventually came out and said, “I didn’t really want to write this song from any kind of political standpoint, or to make a statement. I just wanted to reflect what it feels like”.

3. Tears in Heaven by Eric Clapton

Following the death of Eric Clapton’s four-year-old son, who fell from a 53 story window in New York, the singer/songwriter sat down with Will Jennings to put his emotions into song. At first, Jennings wasn’t sure if he could help Clapton write something so personal, but eventually, they collaborated to create one of the saddest songs ever. Clapton stopped performing the song in 2004, but eventually allowed it to be used in a campaign to inform parents about the risks of falling.

2. Hallelujah by Jeff Buckley

Although this Leonard Cohen song has been covered several times, probably the saddest and most memorable version is that of Jeff Buckley. Ranked number 259 on Rolling Stone’s 500 Greatest Songs of All Times, this performance holds particular weight. Buckley, who died in an accidental drowning at the age of 30, was perhaps one of the greatest stars taken away far too soon. When he sings the final verse, “Well maybe there’s a God above, but all I’ve ever learned from love was how to shoot somebody who out-drew ya”, you can almost feel his heart aching.

1. Hurt by Johnny Cash

Johnny Cash – (HURT) – The best home videos are here

One of the last songs to ever be recorded by Johnny Cash, “Hurt” tells the story of addiction and heart break. Cash’s somber tone and remembrance of his lovely wife, June Carter Cash, who passed just months after was released, brings an extra sentiment to the song. Let’s face it, it isn’t hard to understand why this melancholy tune, sang by an older, dying legend, comes in at number 1 on our list.

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