10 Most Saddest Songs of All Time

Bring out those tissues and handkerchiefs, puresinner has a list of songs to share with you about deaths and loneliness. This is my take on the saddest songs of all time by my favourite artists.

The Cure

Post-Rock pioneers, The Cure carries a lot of dark music and cryptic lyrics in their years of writing. A song which starts with the portrayal of selfishness of a person ended in a huge guilt. It hurts him dearly and even if he pretends wanting to be forgiven, he knows he doesn't deserve to be forgiven.

Elliott Smith
Between The Bars

A man with a low voice and coincidentally prefers to have a low profile, Oscar nominated Elliott Smith is truly missed. Composed with just a simple acoustic guitar, this emotional heartfelt song of loneliness can be felt from the pain he exudes through his music everywhere in his song. When you watch his performances, it's as if the audience isn't there and he's singing in the dark, in his lonely little world. 

10,000 Days

One of a few musicians who often names his musical creations by his mother's name, Maynard James Keenan is a very dedicated son. His grief and pain can be heard from this track and the anger of wanting to blame on someone for her wheelchair bound state for 27 years (equals to 10,000 days) until her death. All he wants is for her to be free from suffering and return home to heaven.

Nine Inch Nails

Trent Reznor has always sang about loneliness and hate for many years and until he got married, which also marked the end of Nine Inch Nails. "Hurt" talks about a life being left by the ones he love most. The pain is what makes life real but not the people closest to him. You can almost hear his cries in every recording of this song and he keeps it sacred in his live shows. The song was also covered by the late Johnny Cash which most critics has reviewed it as the most tragic song sung by Cash because of his death soon after.


Dave Matthews
On Dave Matthews' solo work, "Gravedigger" tell tales of beyond the grave. When you're strolling through a graveyard and you'll see all those names with the date of births and the date of deaths. You'll begin to link the stories behind the tombstones of a mother burying her two sons who was sacrificed in a war and a little boy who died in a bike crash. Matthews sees the gravedigger as the grim reaper, asking him to have some mercy on his death.

It's All Over But The Crying
What makes it harder for a breakup is when you know you still love them but you will never live to have a future with them. Shirley Manson cries about it being all over, life goes on but it still sucks. Every time I have a hard time in my relationship, this song keeps playing in my head.


British band Radiohead makes the list of a few saddest songs sites with all different tracks. I choose "Lucky" because it affects me most ever since I first heard it and it still shares the emotion of losing something or someone from your life.

Pearl Jam
Last Kiss

A cover that made Pearl Jam's highest achievement in the Billboard Top 100 to date, "Last Kiss" echoes vocalist Eddie Vedder into a strong sympathy of pain for this teenage tragedy. The song was written in the early 1960s by Wayne Cochran, Joe Carpenter, Randall Hoyal & Bobby McGlon knowing that tragedy songs are big on making money. It was then unsuccessful but a few artists has since covered it. The song sings about a teenage couple out on a date and ended short after a traffic collision.

Red Hot Chili Peppers
Under The Bridge

One of the band's most successful singles, "Under The Bridge" tells the story of singer, Anthony Kiedis' battle with drugs in the city of angels. His struggle with heroin under the city's bridge where he usually gave in. He sings of his regrets when at that time felt like a whirlwind of adventure. It then ends with a group of choir singing together to Kiedis' hymn.

The Smashing Pumpkins

Another one of those mournings of a son, Billy Corgan also wrote this song after the event of his mother's death. There wasn't a real statement by him saying so but the album was written at the time of her death and it might have had an influence on it. The song might appears to be Corgan questioning his faith in god because of the pain he caused him, tearing him away from his loved one. This is by far one of the best Smashing Pumpkins tracks and the most emotional.


Notable Mentions:
  • "Dead Souls" by Joy Division
  • "Hell Bent" by Kenna

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