Top 10 Saddest Classic Rock Songs

When You Need A Good Cry

More than drugs and sex, heartbreak and pain are common themes in rock ‘n roll too. Some of them will stop you cold and hit you right in the feels, others will just make you cry without warning. Unrequited love, breakup, death – it’s not uncommon for musicians to write about their struggles, relations or inner turmoil. And sadness is universal so pretty much everyone can relate.

It’s not always about the lyrics – sometimes it’s how it’s sung or played. So we recommend taking out your tub of ice cream, maybe a box of tissues to go with it, and just cry your heart out.

10. Simon & Garfunkel – “Bookends”

From the duo that gave us classic hits like “Bridge over Troubled Water” and “The Sound of Silence,” here comes another heart-wrenching song which is short but straight to the point.

Perhaps it’s the simplicity of the track that never fails to pull our heartstrings – whether it’s the melody, two-part harmony or short lyrics, it’s just poignant especially with the lines: “Long ago it must be / I have a photograph / Preserve your memories / They’re all that’s left you.”

“The text refers to the passage of time, and to memories of a loved one, and thus fittingly concludes the series of intervening songs, which address interpersonal relationships at times of life that progress from song to song.” – James Bennighof on using “Bookends” as the first and last song on side one

It doesn’t have to be elaborate to get the point across. And anyone who listens to this is about to be subjected to something so sad, you’ll end up reminiscing all those heartbreaking moments in your life.

9. Nine Inch Nails – “Hurt”

You can be an emotionally stable grown man who hasn’t experienced heartbreak even once in his life and still end up crying like a baby while listening to this. We love Johnny Cash’s version too especially because he made what’s probably the saddest music video ever (tears welled up in our eyes just a few seconds into it) but nothing just beats the original.

“The best anti-drug song I ever heard.” – Johnny Cash

Whether you prefer Nine Inch Nails or Johnny Cash, the sadness it gives you is the same – it’s raw and undiluted. The song opens with one of the most depressing lines ever: “I hurt myself today / To see if I still feel / I focus on the pain / The only thing that’s real.”

And the way it is sung – it’s as if the singer is just weary and drained. Well we’ve all been there, that’s for sure.

8. Alice in Chains – “Nutshell”

The lyrics are dark, ominous and haunting. But it also speaks about despair and even death. We can all feel singer-songwriter Layne Staley’s pain when he sings, “And yet I fight / This battle all alone / No one to cry to / No place to call home.”

For most of his life, he struggled not just with drug addiction but also with depression. And after his death a few years later, the line “I’d feel better dead” becomes even more chilling.

“Since our music is so depressing, everybody expects us to run around in black and whine about shit. But that’s such a misconception. We just get together and fuck around. We’re like the Monkees or something.” – Drummer Sean Kinney

IT IS depressing especially for those currently struggling with something whether it’s with substance abuse or other problems. And we can’t help but think of Staley whenever this comes on.

7. Nazareth – “Love Hurts”

If you say this track didn’t cross your mind when you saw what this list is about, we’d most likely think you’re lying. It’s the sad song EVERYONE knows about and everybody sings – whether it’s during karaoke nights or random jamming sessions.

The opening verse is enough to send you into extreme sadness – “Love hurts, love scars, love wounds / And marks, any heart / Not tough or strong enough.”

Fun Fact: It’s originally recorded by The Everly Brothers but the most successful and popular version is that of Nazareth.

Nazareth’s power ballad just stops you in your track. Even in 2017, it still remains as the universal break up song – nothing just comes close to how painful and emotionally scarring this hit is.

We won’t be surprised if we suddenly start crying because that’s what it does. It’s as if every single sad moment in your life just comes back to you.

6. Tom Waits – “Martha”

Tom Waits’ 1973 classic “Martha” experienced a resurgence after some fans pointed out similarities with Adele’s hit “Hello” and there were those who even accused her of ripping him off. But putting all that aside, “Martha” is proof that the man was clearly a musical genius.

There’s so much sadness from beginning to end that it will basically destroy you whether you can relate to it or not. And these verses just stand out, “Operator, number, please: it’s been so many years / Will she remember my old voice while I fight the tears?”

Fun Fact: Tom Waits was only 24 when this was written.

He sings about an old flame but it’s not so much about the theme that makes you instantly weep, it’s the words and the longing in his voice. For him, there’s nothing sadder than love lost. We may or not have been in his shoes but it’s the whole package – depressing right from the very start.

5. The Doors – “The End”

There’s something beautifully haunting and primordial about this song. It gets creepy and disturbing towards the end but there’s sorrow all over it. It’s a musical masterpiece and one of the saddest parts is when Jim Morrison’s scarred voice sings, “Desperately in need / Of some stranger’s hand / In a desperate land.”

The actual meaning of “The End” is pretty vague. Some say it’s about death while others believe it’s a breakup song.

“Every time I hear that song, it means something else to me. It started out as a simple good-bye song… Probably just to a girl, but I see how it could be a goodbye to a kind of childhood. I really don’t know. I think it’s sufficiently complex and universal in its imagery that it could be almost anything you want it to be.” – Jim Morrison

No matter what it actually means, the fact remains that it’s both depressing and chilling especially when you consider Morrison’s death which took everyone by surprise.

4. Harry Chapin – “Cat’s in the Cradle”

Even if you’re single without any kids, it seriously hurts to listen to this song. Every single word is like a knife that just cuts you. Harry Chapin’s wife Sandy did a brilliant job with this storytelling. The tune may be catchy but looking closely at the lyrics, you’ll understand why this is easily one of the saddest classic rock songs ever written.

It’s basically about a father who’s too busy to make time for his son. It comes full circle when as a grown-up, he becomes too busy for his aging dad.

“”Cat’s In The Cradle” was a combination of a couple of things. Whenever I was on a long drive I would listen to country music, because words would keep me awake more than just music.” – Sandy Chapin

It’s a harsh reality especially for those who grew up with parents who are always working. And that’s perhaps what makes it more sad – almost everyone can relate to how painful it is when a loved one can’t spare a few minutes for you.

3. Pearl Jam – “Black”

It’s Pearl Jam and Eddie Vedder at their absolute best. “Black” is poetic and dark but adding in Vedder’s incredibly sexy voice and it just all comes together. The line “we belong together” just breaks you down.

There’s something exquisite yet sad about Vedder’s vocal performance and we just love how he pours so much emotion into every single verse.

“The song is about letting go. It’s very rare for a relationship to withstand the Earth’s gravitational pull and where it’s going to take people and how they’re going to grow. I’ve heard it said that you can’t really have a true love unless it was a love unrequited. It’s a harsh one, because then your truest one is the one you can’t have forever.” – Eddie Vedder

Ah yes, there’s nothing quite like unrequited love or the loss of a loved one to inspire musicians to create a masterpiece such as this.

Also, can we just take time to appreciate how Vedder’s voice sounds as good as the record?

2. Pink Floyd – “Shine On You Crazy Diamond”

The saddest part of this song is the back story – it was written for former Pink Floyd member Syd Barrett who is responsible for giving the band their name.

He walked in during one of the recording sessions and he looked very different – heavyset and with shaved head and eyebrows. They didn’t even recognize him at first and when they did, Roger Waters was so heartbroken he was moved to tears.

“He came in as we were doing the vocals for “Shine On You Crazy Diamond”, which was basically about Syd. He just, for some incredible reason picked the very day that we were doing a song which was about him.” – Richard Wright

Syd Barrett suffered mental illness due in part to his drug addiction. He was eventually kicked out because he became more unpredictable and would even refuse to play while on stage.

Still, it’s hard to listen to this chilling track without thinking about Barrett and how distressed the rest of the group was after seeing him look strange and miserable.

1. Eric Clapton – “Tears in Heaven”

If this doesn’t make you sad, depressed or cause you to sit in a corner and cry, then you must be made of stone. The moment Eric Clapton sings “Would you know my name if I saw you in heaven?,” we almost always lose it. Whether you know the song’s back story or not, there’s something inexplicably melancholic about it.

But it’s also safe to assume everyone knows who this track is for – Clapton’s 4-year old son Conor who fell from the window of a New York apartment.

“I almost subconsciously used music for myself as a healing agent, and lo and behold, it worked… I have got a great deal of happiness and a great deal of healing from music.” – Eric Clapton

“Tears in Heaven” received multiple nominations and awards but what it will always be known for is the saddest song ever written. More than 25 years after its release, it still tugs on our heartstrings.