Home Love & Relationship 15 Melancholy Songs that Will Leave You Crying Your Eyes Out

15 Melancholy Songs that Will Leave You Crying Your Eyes Out


There’s nothing a like a great sad song to help those tears flow. Everyone needs to cry every once in a while. It’s good for the soul! Crying it out is like a ritual cleansing of all the bad energy that’s been building up inside of you. It could be because of a breakup, the loss of a loved one, a frustrating day at work, or just a mish-mash of pent up emotions that need an outlet.

For all your melancholic needs, here’s a playlist we’ve created just for you. While many sad songs talk about heartbreak and lost love, we’ve tried our best to mix in some other songs that talk about other depressing issues.

So get those tissues ready when you give this playlist a listen because you’re sure to need them!

The Beatles – Yesterday

Let’s start off with a love song whose tune came to Paul McCartney in a dream. The melancholic melody of the song paired with the depressing lyrics made this Beatles song a huge hit with those looking for a good cry. It talks about how love and life was so much easier in the past. But now there are troubles left and right, and it seems like they’re all here to stay.

Lonesome lines: Yesterday, all my troubles seemed so far away

Now it looks as though they’re here to stay

Oh, I believe in yesterday

Suddenly, I’m not half the man I used to be

There’s a shadow hanging over me

Oh, yesterday came suddenly


Gary Jules – Mad World

Of all the covers of this Tears for Fears song, we have to put the one by Gary Jules on this playlist. Mad World is a borderline nihilistic song that seems to say that there’s no point in living anymore. The singer points out the many mundane things he sees each day, realizing that the world is mad because of the pointlessness of people’s actions. In one verse, there’s an allusion to children who seem ignorant of the world, and the singer envies them for their innocence.

Lonesome lines: All around me are familiar faces, worn out places, worn out faces

Bright and early for their daily races, going nowhere, going nowhere

Their tears are filling up their glasses, no expression, no expression

Hide my head, I want to drown my sorrow, no tomorrow, no tomorrow


Pink Floyd – Wish You Were Here

Unbeknownst to many Wish You Were Here is a song for former band member Syd Barrett whose mental dysfunction led to him leaving the band. The song is pleading with Syd to realize that his addiction isn’t the answer to his troubles, even if Syd may not know the difference anymore. Even though Syd’s family denied that he had a mental illness, those who knew him well would be willing to disagree. So as a tribute and a glimmer of hope that he might still change, the other members of Pink Floyd penned this song for him.

Lonesome lines: How I wish, how I wish you were here

We’re just two lost souls swimming in a fishbowl

Year after year, running over the same old ground

What have we found? The same old fears

Wish you were here


Pearl Jam – Black

Eddie Veder says that this song is about his first girlfriend. He says that it’s a song about letting go so that they could each grow as mature adults. It’s a harsh lesson to learn, one that Eddie had to and thus led him to create one of the saddest love songs on this list. In the song you can hear the anguish in his voice, as if each performance is yet a reminder of how he had to let her go.

Lonesome lines: I know someday you’ll have a beautiful life

I know you’ll be a star in somebody else’s sky

But why, why, why can’t it be, why can’t it be mine?


Ben Folds Five – Brick

It starts off with the melodic sound of the piano, and then things go down the sadness spiral from there. Brick is, bluntly put, a song about abortion. Ben Folds and his high school girlfriend had to have an abortion. He maintains that this song is in no way a political statement, but is instead a retelling of the experience and how they both felt about it.

Lonesome lyrics: And we drive, now that I have found someone I’m feeling more alone

Than I ever have before

She’s a brick and I’m drowning slowly

Off the coast and I’m headed nowhere


The Verve – The Drugs Don’t Work

The most popular theory about this song is that it’s about Richard Ashcroft’s father. His father died of cancer when he was 11. From what he could remember, the drugs given to his father no longer worked and he then eventually died. The Drugs Don’t Work is a song about death and how when the one you love dies, it’s like a part of you dies with them.

Lonesome lyrics: If heaven calls, I’m coming too

Just like you said, you leave my life, I’m better off dead


Bob Dylan – Knockin’ On Heaven’s Door

Some of the saddest songs can sometimes be the shortest. “An exercise in splendid simplicity,” as Bob Dylan’s biographer put it. Knockin’ on Heaven’s Door was written for the 1973 film Pat Garret and Billy the Kid.  It’s a story about a dying deputy who feels like he’s right at heaven’s door, just waiting to enter.

Lonesome lyrics: Mama, put my guns in the ground

I can’t shoot them anymore

That cold, black cloud is comin’ down

Feels like I’m knockin’ on heaven’s door


Johnny Cash – Hurt

Here’s another cover on the list that better captures the essence of the song than the original. Johnny Cash’s version of this song is even sadder still because it was one of his final hits before he died. When you listen to the lyrics closely, you can see that it’s about self-harm, addiction, and the struggle of finding a reason to live in spite of the pain.

Lonesome lyrics: I hurt myself today to see if I still feel

I focus on the pain, the only thing that’s real

The needle tears a hole, the old familiar sting

Try to kill it all away, but I remember everything


Eric Clapton – Tears in Heaven

Tears in Heaven was written by Eric Clapton in the aftermath of his son’s death. His son, Connor, was only 4 years old when he fell from the 53rd floor of an apartment. Clapton intentionally tried to be ambiguous about this in the lyrics because he also wrote it for the movie Rush. But whether you know the backstory of the song or not, you must admit that it’s one of the saddest songs out there.

Lonesome lyrics: Would you know my name if I saw you in heaven?

Would it be the same if I saw you in heaven?


A Great Big World – Say Something

Now on to something relatively new. Say Something seems to have an ambiguous meaning and can relate to love, friendship, or even death. To most, it’s a song about loving someone so much and yet being forced to give up on that love. It’s as if the singer is giving the other person so many chances to keep their relationship afloat, but ultimately, it doesn’t work out.

Lonesome lyrics:  Say something, I’m giving up on you

And I’m sorry I couldn’t get to you

Anywhere I would have followed you

Say something, I’m giving up on you


Sinead O’Connor – Nothing Compares to 2 U

There are some songs that, while sad, may often seem routinely performed by the artist. But this one by Sinead O’Connor simply must be listened to along with the music video. In it you can see and hear her anguish with each line. She sings about being able to do whatever she wants now that someone in her life (in this case, her mother) is gone. But despite this, nothing can seem to take away her grief.

Lonesome lyrics: Since you been gone I can do whatever I want

I can see whomever I choose

I can eat my dinner at a fancy restaurant

But nothing, nothing can take away these blues


George Jones – He Stopped Loving Her Today

Death, love, anguish – all of those things in this beautifully melancholic song from 1980. This song is about man who stayed in love with the same woman all these years, even after she left him. He keeps her love letters hoping she’d come back. Until finally, he passes away – and that’s the day he stopped loving her.

Lonesome lyrics: He stopped loving her today

They placed a wreath upon his door

And soon they’ll carry him away

He stopped loving her today


Jimmy Eat World – Hear You Me

The song was written as a tribute to sisters Mykel and Carli Allan, who were friends and supporters of many unknown LA bands at the time including Jimmy Eat World. They died in a car crash in July, 1997, thus inspiring this song. Hear You Me  is a beautifully sad song about wishing they could have at least thanked the sisters one last time before they passed.

Lonesome lyrics: And if you were with me tonight

I’d sing to you just one more time

A song for a heart so big

God wouldn’t let it live


Bloc Party – Signs

Grief is a complex emotion that many people experience differently. In this case, grief is exemplified by the signs they see all around them – from ravens to dreams. In a way, he’s still in denial, hoping that it’s not true that the one he loves is dead. He wants so hard to believe that she’s not really dead, just sleeping. And so he clings on to the dreams in which he sees her.

Lonesome lyrics: I see signs now all the time

That you’re not dead, you’re sleeping

I believe in anything

That brings you back home to me


Les Miserables – I Dreamed a Dream

Last on our list is this song that’s sure to leave you an emotional wreck. I Dreamed a Dream is sung by the tragic character, Fantine, when she is thrown out in the streets after getting fired from the job. What really makes this song extremely depressing is that the song describes how hopeful and naïve she used to be in the days of her youth. But now that she has been cast out, she realizes that what she used to dream about and what she is now are very different.

Lonesome lyrics: I had dream my life would be

So different from this hell I’m living

So different now from what it seemed

Now life has killed the dream I dreamed

If these songs don’t leave you a teary-eyed mess, then we don’t know what will!


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