From Billie Holiday to Jeff Buckley: The 10 saddest albums of all time (2023)

Bob Marley once said, “One good thing about music, when it hits you, you feel no pain.” But the same can’t be said about the songwriters who wrote these ten heartbreaking albums. Guaranteed to grab you by the tear ducts, these records will leave you blubbering for their enigmatic content, their solemn messages and their authentic emotion.

By peeling back the curtain, the tumultuous personal lives that often ended in tragedy are revealed, giving a lot of insight into why these albums were so imbued with sadness. The record not only provides a reminder of the artist behind the artistry but also helps us all to connect with our own emotions.

That’s the real beauty of sad music, it allows one, sometimes, to find happiness again. There’s a camaraderie that permeates truly fraught music, a knowledge that somebody else feels or has felt the same as you, all with the added bonus of creating beautiful music along the way. It’s why sad music has become such a joyful experience for many who revel in it. Cathartic and authentic, these albums are perfect for a good cry.

So, pull out your tissues. Here are our picks for the ten saddest albums of all time.

10 saddest albums of all time:

10. Miles Davis– Blue Moods (1955)

Consisting of only four songs, Miles Davis’s 1955 release is the epitome of cool jazz while also bringing in an edge that would become his signature moody sound for years to come. In songs like ‘Alone Together’, Davis mixes sorrow and nostalgia with his masterful touch.

While Davis’s trumpet playing is the true shining star of the record, he also collaborated with Charles Mingus (whose record label Debut Records it was released on) on bass, Britt Woodman on trombone, Teddy Charles on vibraphone, and Elvin Jones on drums.

It’s some of his most arresting work and charged with complete emotion.

From Billie Holiday to Jeff Buckley: The 10 saddest albums of all time (1)

9. Lana Del Rey – Ultraviolence(2014)

Lana Del Rey’s third studio album proved to trade her pop princess image, favouring a new vision of a dark monochromatic anti-heroine. Working with The Black Keys member DanAuerbach, Del Rey crafted a jazz-infused, Lou Reed-Esque album, equally dark in tone and subject matter.

(Video) Billie Holiday - "Strange Fruit" Live 1959 [Reelin' In The Years Archives]

Speaking in an interview shortly after the album’s release, she shocked the interviewer by stating, ”I wish I was dead already.” It provoked an outpouring of controversy but underlined the message of the record.

With reoccurring themes such as abandonment, misery, and heartbreak explored in tracks like ‘Sad Girl’ and ‘Pretty When You Cry,’ it isn’t one to lift your spirits. Seeing the state of mind she was in during that era, it’s no surprise whyUltraviolenceturned out so grim.

From Billie Holiday to Jeff Buckley: The 10 saddest albums of all time (2)

8. Joy Division – Closer (1980)

Released two months after the suicide of lead singer Ian Curtis,Closeris now associated with tragedy, and as a result, forever remembered as a devastating piece of art.

When recalling Curtis’s state of mind during the albums recording, Joy Divison’s lead guitarist, Bernard Sumner, mentioned that “He [Curtis] had this terrible claustrophobic feeling that he was in a whirlpool and being pulled down, drowning.”

The use of moody synth creates an almost claustrophobic atmosphere underneath melancholy lyrics certainly reflects Curtis’s state of mind. But despite the sadness surrounding it,Closerbecame a pioneering force in the post-punk era.

From Billie Holiday to Jeff Buckley: The 10 saddest albums of all time (3)

7. Nirvana– In Utero (1993)

In the third and final studio album released by Nirvana, the band ditched the polished pop-adjacent sound they achieved inNevermindand opted for a more natural feel that would showcase the emotional rawness of Cobain’s lyrics— but the lyrics were far from soothing.

Cobain tragically passed away from suicide only seven months after its release, which gives an insight into the masterful lyrics that showcase his possible emotional state during the album’s recording.

(Video) Artists Who Changed Music: Billie Holiday

It’s one of the most poignant records released in that decade and still breaks our hearts when we drop the needle. Written by a man dealing with serious pain, it’s no surprise it can still make us weep.

From Billie Holiday to Jeff Buckley: The 10 saddest albums of all time (4)

6. Lou Reed – Berlin (1973)

Coming off the back of his glam rocking releaseTransformer, which revived his career and sent him into newfound commercial stardom, Lou Reed’s 1973 releaseBerlinseemed to flip his cheery discography on its head.

The concept album showcases heavy themes such as abuse, addiction, and depression, and was initially received poorly by the public. But over the years, it’s gained a new appreciation for its brutally honest depiction of the culture’s underbelly.

There’s something heartbreaking about hearing Reed’s descent into depravity, one that he was more than happy to push along. The singer struggled throughout his life to come to terms with himself and this album reeks of the desperation for contentment.

From Billie Holiday to Jeff Buckley: The 10 saddest albums of all time (5)

5. Billie Holiday – Lady Sings The Blues (1956)

Released simultaneously with her ghostwritten autobiography of the same name, Billie Holiday’sLady Sings The Blues seemed to encapsulate her heartbreaking account of struggle— mentally, physically, and racially.

The album’s content was taken from taped session recordings from 1954 to 1956, where she was backed by tenor saxophonist Paul Quinichette, trumpeter Charlie Shavers, pianist Wynton Kelly, and guitarist Kenny Burrell.

Heavily addicted to heroin and trying to come to terms with her childhood traumas, Holiday sings with an unbelievable rawness, which is at its prime in the album.

(Video) Jeff Buckley - Lover, You Should've Come Over (Audio)

From Billie Holiday to Jeff Buckley: The 10 saddest albums of all time (6)

4. Joni Mitchell –Blue (1971)

No album has so fittingly represented its title better than Joni Mitchell’s 1971 release. Submerged in blue on the cover, Mitchell’s lyrics are equally so as she sings of loss and heartbreak.

Despite being recorded in sunny California, where Mitchell was spending time with friends and contemporaries like David Crosby and Graham Nash, it seems she was living in a much darker place emotionally.

“TheBluealbum, there’s hardly a dishonest note in the vocals,” reflected Mitchell in a 1979 interview. “At that period of my life, I had no personal defenses. I felt like a cellophane wrapper on a pack of cigarettes. I felt like I had absolutely no secrets from the world and I couldn’t pretend in my life to be strong. Or to be happy. But the advantage of it in the music was that there were no defenses there either.”

Poised and poignant, it’s easily one of Joni Mitchell’s best albums and certainly her saddest.

From Billie Holiday to Jeff Buckley: The 10 saddest albums of all time (7)

3. Jeff Buckley– Grace (1994)

For a debut studio album release, Jeff Buckley’sGraceappeared to be the moodiest of his work to date. But from its dreaminess and sorrow came a trailblazing album that almost defied genre, prioritising the music’s ambience and feel above all.

Despite its poor initial sales and reception,Gracehas become critically acclaimed, with Jimmy Page deeming it his “favourite album of the decade” and David Bowie calling it the one album he would take to a desert island.

Buckley’s unexpected drowning in the Mississippi River three years later only adds to the intoxicating allure and unbelievable sadness of the singer’s only studio release.

(Video) Jeff Buckley - Last Goodbye (Edit)

From Billie Holiday to Jeff Buckley: The 10 saddest albums of all time (8)

2. Sufjan Stevens – Carrie & Lowell (2015)

Inspired by the 2012 death of his mother, Carrie, while also referring to her second husband Lowell Brahms, Stevens created an unbelievably raw depiction of grief inCarrie and Lowell. On the record, he comes to terms with his mother’s mental health issues and his own abandonment. It’s pure heartbreak in every note.

Stevens later recalled that during the process of creating the album: “I was recording songs as a means of grieving, making sense of it. But the writing and recording wasn’t the salve I expected. I fell deeper and deeper into doubt and misery. It was a year of real darkness. In the past my work had a real reciprocity of resources—I would put something in and get something from it. But not this time.”

There are few albums that are capable of leaving whoever hears it in tears, but this album is certainly one of those rare gems.

From Billie Holiday to Jeff Buckley: The 10 saddest albums of all time (9)

1. Nick Drake– Pink Moon(1972)

In contrast to his previous album, forPink Moon, Nick Drake wanted to strip down his sound and get back to the basics. Using onlyacoustic guitar and a brief piano riff overdubbed onto the title track, Drake recorded theentirety of the album in only two late-night sessions at London’s Sound Technique Studios.

Drake would die tragically only two years later at the young age of 26 and knowing what we know about his battle with depression, the raw lyrics and simple composition hit even harder, making it arguably the saddest album of all time.

Pure in its poignancy, the album deserves all your attention and a truly active listener.

From Billie Holiday to Jeff Buckley: The 10 saddest albums of all time (10)

We’ve got the ten saddest albums of all time for you in one handy playlist, below:

(Video) The Most Beautiful Version of "Hallelujah" You Have Ever Heard


What is the saddest Lana Del Rey album? ›

It's a quite popular opinion that Ultraviolence is considered her most depressing album and each album released after gets happier and happier, with NFR being the most cheerful album.

What is the number 1 album in history? ›

Michael Jackson's Thriller, estimated to have sold 70 million copies worldwide, is the best-selling album ever. Jackson also currently has the highest number of albums on the list with five, Celine Dion has four, while the Beatles, Pink Floyd, Madonna and Whitney Houston each have three.

What is the most played religious song at a funeral? ›

One of the more common and well-known songs, "Amazing Grace" is a great pick for a Christian funeral song. It's an easily recognizable song, so funeral attendees can sing along to it to celebrate the life of the deceased.

What is the least liked song ever? ›

"Friday" has been widely described as the worst song ever recorded, attracting derision for its weak lyrical content and its vocals that were excessively processed by Auto-Tune. Produced by Patrice Wilson, the song became an Internet sensation, making it the subject of multiple parodies and ridicule.

Was Lana Del Rey a addict? ›

That didn't work, and eventually drugs other than alcohol also became a part of Del Rey's story. It wasn't long before she left school and went to rehab. According to the GQ interview, Del Rey eventually began working at an outreach program for addicts and alcoholics, and she continued to do this well into adulthood.

What does Lana Del Rey's tattoo say? ›

Del Rey has two tattoos on her right hand. One is the phrase "trust no one", and "die young" is tattooed on her ring finger.

What is Lana Del Rey's lowest note? ›

Lana Del Rey's vocal range is approximately 3 octaves and minor third, spanning Bb2 – F#5 – C#6.

Who is the #1 selling artist of all time? ›

Top-selling artists worldwide as of 2022. Perhaps unsurprisingly, British rock band The Beatles are top of the list for best-selling artists worldwide, with 183 million units certified sales. Second is Garth Brooks with over 157 million units sales, followed by Elvis Presley with 139 million units.

What is the deepest singing voice? ›

Since 2012, Tim Storms has held the world record for the lowest ever vocal note – that's a deliciously gravelly G -7 (0.189 Hz), which is eight octaves below the lowest G on the piano.

What is considered the best song ever written? ›

Aretha Franklin's 'Respect' named Greatest Song of All Time by Rolling Stone.

What is the #1 Christmas song of all time? ›

According to the Guinness Book of World Records, "White Christmas" by Bing Crosby is not only the best-selling Christmas/holiday single in the United States, but also the best-selling single of all time, with estimated sales in excess of 50 million copies worldwide.

What song do you not play at a funeral? ›

15 Most Inappropriate Funeral Songs

Another One Bites the Dust by Queen. Always Look On the Bright Side of Life by Eric Idle. Ding Dong! The Witch is Dead from The Wizard of Oz.

What is the number one requested funeral song? ›

“My Way” by Frank Sinatra. “Time To Say Goodbye” by Andrea Bocelli. “Over The Rainbow” by Eva Cassidy. “Wind Beneath My Wings” by Bette Midler.

What is the most played song at a Catholic funeral? ›

1 – The Lord's my Shepherd

This most popular funeral hymn is based on the words of Psalm 23. The hymn is very well known and has been sung by many at school, and has been sung at many notable Royal occasions.

What is a happy song to play at a funeral? ›

Uplifting funeral and memorial songs

If you want to raise everyone's spirits, play one of these uplifting memorial songs: “Simply the Best” by Tina Turner. “Always Look at the Bright Side of Life” by Monty Python. “Somewhere Over the Rainbow” by Israel Kamakawiwo'ole.

What is the slowest song ever written? ›

Organ2/ASLSP (As Slow as Possible) is a musical piece by John Cage and the subject of one of the longest-lasting musical performances yet undertaken. Cage wrote it in 1987 for organ, as an adaptation of his 1985 composition ASLSP for piano. A performance of the piano version usually lasts 20 to 70 minutes.

Who is Lana Del Rey's lover? ›

All About Lana Del Rey's Boyfriend Jack Donoghue.

Was Lana Del Rey's father rich? ›

Rather than being an outsider struggling for recognition, Del Rey is in fact the daughter of a millionaire father who has backed her career.

Why did Lana Del Rey cry? ›

Lana Del Rey admitted that her on-stage tears during the Dublin leg of her tour last year were the result of a medical issue, and not down to being lost in her song. The singer began crying on stage during her performance of 'Video Games', with most people believe she was just getting into the moment of the song.

What does Lady Gaga's arm tattoo say? ›

Lady Gaga has a German quote on her arm.

The tattoo is in German and translates to: "Confess to yourself in the deepest hour of the night whether you would have to die if you were forbidden to write. Dig deep into your heart, where the answer spreads its roots in your being, and ask yourself solemnly, Must I write?"

Why does Ariana Grande have so many tattoos? ›

Ariana Grande may only be 27 years old, but she already has more tattoos than candles on her birthday cake. The “Thank U, Next” singer is covered in tributes to her dogs, celestial designs, Harry Potter references, song lyrics and more, many of which were done by her go-to tattoo artist Girl Knew York.

What is Angelina Jolie tattoo? ›

Angelina Jolie's Roman Numeral Tattoo

On the left, it reads “XIII V MCMXL,” which is 13/5/1940. It is a tribute to Winston Churchill in remembrance of the “blood, toil, tears and sweat” speech that he delivered on the same day.

What is Adele's lowest note? ›

When we take into account all of her song releases (without studying each and every live performance), her lowest note sung is a C3 in the performance for "Million Years Ago" as heard in the first verse. It's a surprise to hear her lowest note in a live performance vs.

What is Beyonce's voice type? ›

Beyoncé is basically an operatic mezzo-soprano in disguise – and she proved it in this impressive clip.

Is soprano 1 higher than soprano 2? ›

In choral music

Sopranos commonly sing in the tessitura G4-A5. When the composer calls for divisi, sopranos can be separated into Soprano I (highest part) and Soprano II (lower soprano part).

What sad music does to the brain? ›

Sad music tricks the brain into engaging a normal, compensatory response by releasing prolactin. In the absence of a traumatic event, the body is left with a pleasurable mix of opiates with nowhere else to go. Prolactin produces feelings of calmness to counteract mental pain.

Why do depressed people love music? ›

Sad music also triggers the release of a hormone called prolactin, which can help reduce feelings of grief. Since the feeling of sadness, which led the brain to release the hormone, was second-hand — there's no actual grief the person experienced that needs consoling, so the hormone just leaves them feeling happy.

Do sad songs cure depression? ›

In this study, participants reported feeling better after listening to sad music, not that it perpetuated a low mood as was previously thought. As study co-author Jonathan Rottenberg said, “They actually were feeling better after listening to this sad music than they were before”.

Why do depressed people listen to music? ›

Research suggests that people with depression find sad music calming — or even uplifting. A 2015 study found that people diagnosed with depression were more inclined to listen to sad music. The researchers believed, then, that this finding meant depressed individuals sought to maintain their low mood.


1. Bon Jovi - Hallelujah
(Bon Jovi)
2. Jeff Buckley - Grace (Official Video)
(Jeff Buckley Music)
3. Jeff Beck, Rod Stewart - People Get Ready
(Rod Stewart)
4. Jeff Buckley - Hallelujah (Official Video)
(Jeff Buckley Music)
5. Jeff Buckley - You and I Album Trailer (Pt. 2) (Digital Video)
(Jeff Buckley Music)
6. Chet Baker - Almost blue
Top Articles
Latest Posts
Article information

Author: Terence Hammes MD

Last Updated: 02/24/2023

Views: 5920

Rating: 4.9 / 5 (49 voted)

Reviews: 80% of readers found this page helpful

Author information

Name: Terence Hammes MD

Birthday: 1992-04-11

Address: Suite 408 9446 Mercy Mews, West Roxie, CT 04904

Phone: +50312511349175

Job: Product Consulting Liaison

Hobby: Jogging, Motor sports, Nordic skating, Jigsaw puzzles, Bird watching, Nordic skating, Sculpting

Introduction: My name is Terence Hammes MD, I am a inexpensive, energetic, jolly, faithful, cheerful, proud, rich person who loves writing and wants to share my knowledge and understanding with you.