TOP 15 Saddest Songs Of All Time
Sometimes, we all need a truly sad song. Not just a slightly melancholic tune with darkish lyrics or shaky vocals, but a track that comes with a gut-wrenching emotion of real sadness. The kind of sadness that brings tears to your eyes, that lets you stop holding back and just feel. The kind that, in some strange way, makes your own emotions a little easier to bear.
I think for me, the only depressing music is music that doesn’t give credence to those kinds of feelings, music that’s just written for money or commercial reasons. Sad music can be the most uplifting thing in the world.
Conor O’Brien
I love this quote by Conan – it summarizes the point quite clearly. That’s why I wanted to create my list of the saddest song of all time. Because I do believe that many will find it helpful and, hopefully, even healing. After all, the positive effects of music have been proved in multiples studies, including this “Music therapy for depression“, published in PubMed Central.
So, here they are – these are the saddest songs of all time. Incredibly powerful compositions that will break your heart and then help you piece it back together.
I’ve included Spotify and YouTube players with all the music, so you can listen to it right here.
TOP 15 Saddest Songs Of All Time
As always, I’ve carefully handpicked every song for this chart. This isn’t just another copy-paste selection of the same old tracks that websites on the first page of Google keep repeating. No, I genuinely love music and I don’t need to check generic lists to know which songs truly capture sorrow and raw emotion.
I ranked the songs based on my personal experience and thorough research, but that shouldn’t affect how you feel about them. What you consider the saddest song really depends on what resonates with you, and that’s gonna be your ultimate truth.
15. Jeff Buckley – Hallelujah
Jeff Buckley’s Hallelujah is one of the most profound musical experiences I’ve ever had. The raw, aching emotion in his voice, the immaculate guitar work, the delivery of the lyrics… If you open your heart to this song, it just might overwhelm you.
Often regarded as one of the saddest songs ever, it continues to resonate with countless people facing heartbreak or grief. Buckley’s untimely passing only deepened the song’s tragic weight.
14. Sarah McLachlan – Angel
Angel is one of the most beautiful and heartfelt songs ever recorded. Released in 1997, it remained popular over the years. Its delicate beauty and sincerity creates undeniable deep emotional connection.
No wonder it has been featured in numerous films and TV series during their most powerful, dramatic moments. Notable examples include Dawson’s Creek, Smallville, and City of Angels (1998), where it was part of the official soundtrack.
13. Goo Goo Dolls – Iris
If there were an ultimate relationship song, Iris by Goo Goo Dolls might just be it. Unconditional love and sacrifice are at the heart of this track, with lyrics, vocals, and music blending perfectly.
Written for the 1998 film City of Angels, the song reflects the story of an angel (Nicolas Cage) who falls in love with a human (Meg Ryan) and is willing to give up eternity just to be with her. And if you’ve seen the movie you’ll know why it is so sad.
12. Staind – Something To Remind You
If you’ve never heard Staind, you’re missing out on one of the most unique and compelling nu metal bands of the early 2000s. You’re also missing their masterpiece, Something to Remind You.
This song is beautiful. Powerful lyrics, raw intensity, and Aaron Lewis’ remarkable vocals come together to create an unforgettable and intense listening experience.
11. Ella Henderson – Missed
Ella Henderson rose to fame after her standout performances on The X Factor. Missed – the song she chose for her audition – is deeply personal, written as a heartfelt tribute to her grandfather. That first performance stunned both judges and viewers, you could literally see people crying.
With Ella’s powerful voice, the song captures raw emotion, delivering a pure, relatable sadness that we all can relate to.
10. Myles Kennedy (Alter Bridge) – Watch Over You
Myles Kennedy is one hell of a singer and guitarist. He’s actually a fan of Jeff Buckley, whose song also made this list. Kennedy even delivered a stunning cover of Hallelujah himself.
But it’s Watch Over You from Alter Bridge’s iconic album Blackbird that hits home the most. The lyrics and Kennedy’s delivery are so deeply personal and direct, making this song damn special.
9. The Mayan Factor – Beauty And The Beast
The Mayan Factor is a relatively unknown band from Maryland, yet in just two albums In Lake ‘ch (2003) and 44 (2005) they created some of the most hauntingly beautiful and sorrowful music I’ve ever heard. The combination of mysterious lyrics and unforgettable vocals is incredibly captivating.
Unfortunately, lead singer Ray Schuler passed away in 2011, leaving these songs as his legacy.
8. Frank Sinatra – Autumn Leaves
Frank Sinatra needs no introduction – the man is a legend. And while most listeners know him for his swing and jazz hits, this song Autumn leaves from Where Are You? (1957) is a hidden gem.
The depth of emotion, the sorrow, and the sheer melancholy in his voice make this song truly mesmerizing. It’s Frank Sinatra you rarely hear, but the one you definitely should know.
7. Johnny Cash – Hurt
Johnny Cash’s version of “Hurt” is such a sad song because it feels like a final goodbye. The man’s voice is worn and you can literally feel all the emotional pain in it. Every word sounds real, there’s no pretending at all.
Knowing that Cash recorded it near the end of his life makes it even more heartbreaking, honestly. And the music video clip only elevates this overwhelming feeling of sadness.
6. Damien Rice – The Blower’s Daughter
One of the most recognizable and iconic songs by Damien Rice, The Blower’s Daughter is a haunting and powerful ballad. It radiates with emotions of love, loss, and heartbreak.
And like many songs on this list, it is just as sad as it is beautiful. If you’re not familiar with Damien Rice music, you’re in for a treat.
5. Nick Drake – Clothes of Sand
This is one of many beautiful songs by Nick Drake. But something about Clothes of Sand makes it feel especially mysterious, longing and fragile. The inherent sadness in Drake’s voice manifests itself in this track even more that in others.
Its haunting melody, poetic lyrics, and Nick’s delicate vocals create an atmosphere that stays in your heart long after the song ends.
4. Whitney Houston – I Will Always Love You
Possibly one of the greatest vocal performances ever, and definitely one of the best love songs of all time. I Will Always Love You is a super-hit, it’s truly timeless.
It’s beautiful and sad at the same time. Especially knowing that Whitney is not with us any longer.
3. Jackson C. Frank – Milk and Honey
The tragic life story of Jackson C. Frank is not widely known among music fans, yet he created some of the most beautiful and sorrowful compositions of all time. I could easily choose multiple songs of his for this chart, and they all would be perfect.
But today, I’ve selected Milk and Honey. It features a stunning melody, Frank’s unique voice, an incredible guitar sound, and an emotional delivery that’s truly one of a kind.
2. The Cinematic Orchestra – To Build A Home
To Build a Home is one of the most magical songs ever written and performed. And also one of the saddest. Everything about it is spectacular – it cries with pure emotion.
Just sit down, put on your headphones, close your eyes, and play it. You’ll never be the same again.
1. James Blunt – Monsters
James Blunt is one the most genuine singers I’ve heard. He pours his soul and heart in every song. He wrote Monsters as a sort or farewell to his dad, who was battling a chronic illness. And man – you can feel those emotions right away.
The way James sings it, especially in the official music video, is absolutely heartbreaking. It hits hard every time and always brings tears to my eyes.
Spotify Playlist of The Saddest Songs Ever
You can listen to All these tracks via this Spotify online player.
YouTube Playlist of The Saddest Songs
If you enjoy watching music videos and listening to the songs at the same time, you might prefer this YouTube player instead. This is the same playlist as on Spotify.
Bonus Honorable Mentions
The beauty of music lies in its diversity and the richness of great artists and musicians. Over the years, thousands of songs have been recorded, and I won’t pretend to know every name or that I’ve heard every single one. But because music is such a huge part of my life, I listen to it constantly, exploring different genres, eras, and styles.
That’s how I keep discovering hidden gems. And while I’ve chosen the songs above for The 15 Saddest Songs in History chart, I still have more music to share.
These next 10 songs are just as powerful in their emotional impact. In fact, you may find them even deeper. Consider them bonus honorable mentions.
- Grey Daze – Morei Sky
- Moving Atlas – Just Crash Anywhere (acoustic)
- Anathema – Lost Control
- Agua de Annique – Come Wander With Me
- Ray LaMontagne – Lesson Learned
- Piers Faccini – Strange Is The Man
- Damien Jurado – Silver Joy
- Armand Amar – Whales
- Angus & Julia Stone – Draw Your Swords
- Adele – Someone Like You
Don’t worry – I’ve put all these songs into a separate Saddest Songs in History: Bonus Playlist for you right here:
To Sum it Up
Sad songs usually touch such themes as love, heartbreak, loss, grief, loneliness and regret. They can be about breakups, missing someone, feeling alone, saying goodbye, or looking back on the past with sadness. But no matter the topic, sad songs hit hard because they are relatable – we all go through these thing in our own lives.
To make this Saddest Songs Ever chart I gathered the most touching and sad compositions I’ve heard. I also listen to hundreds of songs other people mention.
Maybe you have your own songs that break your heart every time you listen to them. That’s completely fine, we all have our preferences. I just hope you’ve found something real in my list as well. Something that only music can deliver.
