We reviewed the 63 best sad songs of all time, so you don’t have to!
Our list will help you find the song you want to cry out the bad times to. A sad song provides a personal connection for you as you move through your negative emotions after your life has hit you hard.
1. Nothing Compares 2 U by Sinead O’Connor
Sinead O’Connor has had a tough life but her career hit heights with this Prince cover. One of the saddest songs of all time began life as a minor pop hit for Prince and The Family. O’Connor gave the song a new lease of life with haunting vocals and synth strings. The promo for the song became famous for the single tear O’Connor cries dressed in black against a dark background in extreme closeup.
Next: Best love songs to play for him
2. Traitor by Olivia Rodrigo
Breakup songs are not always written by classic pop and rock stars. Olivia Rodrigo is bringing modern heartbreak to the masses, with Traitor, a classic in the making. The song focuses on the impact of emotional cheating on her and her relationship.
Next: Best songs about cheaters in relationships
3. Hurt by Johnny Cash
Johnny Cash had not been relevant in decades when producer Rick Rubin convinced the man in black to cover some popular songs. Nine Inch Nails writer, Trent Reznor, was not convinced Cash would produce anything but a gimmicky version of his song. After video looking back on the life and career of Cash and his family, Reznor agrees this turned this aching song of loss into a classic to cry to.
Next: Top songs that everyone knows
4. Teardrop by Massive Attack
Massive Attack was the biggest star in trip-hop at the turn of the century. Teardrop was a departure because of its haunting melody and a vocal completed by Elizabeth Fraser. Fraser was mourning the loss of her boyfriend, Jeff Buckley, during the recording sessions for Teardrop, adding another layer of loss to the song.
Next: The best sad love songs of all time
5. Back to Black by Amy Winehouse
Amy Winehouse is remembered for all the wrong reasons. Her personal battles against addiction and a messy personal life have overtaken the fragile nature of her writing and lyrics. If you want to cry over a breakup or loss of some aspect of life, Back to Black gives you all the ammunition you need to cry.
Next: Songs about missing someone you love dearly
6. Doing it Wrong by Drake
Drake’s album, Take Care, is 20 songs of emotion and unhappiness. Doing it Wrong jumps to the top of the list of Drake’s great breakup songs. The emotion of the artist comes through and will help you channel your unhappiness.
Next: The best sad rap songs of all time (depressing hip hop tracks)
7. Love is a Laserquest by Arctic Monkeys
Arctic Monkeys began life as a post-punk band and have morphed into a rock behemoth. Spending an afternoon at a Laserquest may not be your idea of the backdrop to a classically sad song to cry to. Alex Turner’s lyrics and a stripped-back production add to the yearning of the song that includes imaging the lost love as “just some lover”.
Next: The top sad rock songs ever recorded
8. The Boxer by Simon & Garfunkel
The fall of the World Trade Center Towers during 9/11 saw Simon & Garfunkel perform The Boxer at several memorial concerts. The song was chosen by the artists because of its sense of loss for the American Dream. Despite the sadness of the song, it rises to an image of the boxer refusing to accept defeat from his opponent.
Next: The best songs about 9/11 of all time
9. No Distance Left by Blur
Blur are best known for their stadium-rocking anthem, Song 2. The Parklife band showcased their sensitive side with No Distance Left. Lead singer, Damon Albarn was going through the breakup of his long-term relationship when he penned this sensitive ode to his lost love.
10. Angie by The Rolling Stones
Angie is a song about yearning for a lost love. Crying over some form of loss is easy when you listen to Mick Jagger’s aching vocals for the song. Keith Richards is known to have written the body of the song, with Jagger contributing lyrics concerning the breakup of his relationship with Marianne Faithfull.
11. I’m So Lonesome I Could Cry by Hank Williams
Country music has always walked the fine line between happiness and despair. Hank Williams tipped over the edge of the cliff into despair with I’m So Lonesome I Could Cry. The lyrics of the song showcase the crack in Williams’s voice as he laments the loss of his love.
Next: Best songs about death and losing people
12. Swim Good by Frank Ocean
Frank Ocean broke into the mainstream with Swim Good. The song is bleak and unhappy as it depicts the depression and unhappiness of Ocean’s main character. The suicidal thoughts and sense of despair are on full show as he contemplates suicide.
Next: The best songs about suicide
13. Tear in Your Hand by Tori Amos
Tori Amos made a living out of heartbreak in the 1990s and early-2000s. Tear in Your Hand is a masterpiece of the sad song genre. The song tells the story of a woman who is going through a painful breakup and contemplating the meaning of her life.
Next: The absolute best songs from the 1990s
14. Wish You Were Here by Pink Floyd
The story of Pink Floyd founder, Sid Barrett, is sad and bizarre. Bandmate, Roger Waters wrote Wish You Were Here for his unwell bandmate and created a classic song of loss and regret. The song becomes all the more poignant when you hear the story of Barrett arriving at the recording unannounced and unrecognizable.
15. Shallow by Lady Gaga and Bradley Cooper
Gaga’s performance in A Star is Born was impressive and backed up Cooper’s belief in her acting abilities. We couldn’t have guessed Cooper had such a singing talent and gives a heartbreaking opening to the movie’s main theme. Produced by Amy Winehouse collaborator, Marx Ronson, Shallow gives Lady Gaga the freedom to explore her vocal talents to the fullest.
16. Piledriver Waltz by Alex Turner
The movie, Submarine is a classic coming-of-age drama of teenage heartbreak. Piledriver Waltz by Arctic Monkeys frontman, Alex Turner encapsulates the desperation of a teenager knowing his first romance is coming to an end. The song makes you cry and feel euphoric in equal measure throughout.
17. Just Like Heaven by The Cure
Robert Smith’s devotion to the goth aesthetic sometimes takes away from his brilliance as a songwriter and performer. Just Like Heaven turns up the gothic sadness to 11 and lets Smith wallow in losing his love. The song is powerful and emotional, with Smith’s vocals providing listeners with the chance to cry in abundance.
18. Pink Moon by Nick Drake
Brad Pitt became the champion of Nick Drake’s lost brilliance in the late-1990s. The English singer-songwriter has his own sad story that is reflected in the melancholy of his voice. Drake had a very English sense of sadness and wordplay, which is on full show in the haunting melody of Pink Moon.
Next: The top songs about the moon and lunar themes
19. Into My Arms by Nick Cave & The Bad Seeds
“I don’t believe in an interventionist God” is one of the great opening lyrics of all time. Cave’s deep baritone accompanied by a piano shows that great songwriting does not need huge production values to be emotional and effective. The Australian is an emotional and complex character whose own tragic life is dripping through every lyric.
20. What About Us by Pink
Going through a breakup is tough and Pink gives us the knowledge she has been through her own share of hard times. The song is filled with lyrics depicting her belief in a happy future and how her lost love has broken her dreams.
21. Everybody Hurts by R.E.M.
Before R.E.M. lost sight of what they did best, their Losing My Religion album made them a leader of the 1990s indie scene. Everybody Hurts remains a classic song about loss and holding onto the hope we all have for the future. Michael Stipe’s soprano voice cracks and calls to the listener to tell us we all hurt at some time in our lives.
Next: The top soprano songs to sing
22. A Case of You by Joni Mitchell
Joni Mitchell wrote one of the classic breakup songs and sums up the feelings most of us have at some point in our lives. Mitchell’s stirring vocals are on full display as she explains her lost love called her “as constant as the Northern Star” before breaking up with her. Tissues are needed whenever this song is played.
23. Laura by Bat For Lashes
Bat For Lashes proves the saddest of songs does not have to be about a breakup. Instead, this classic tells the story of Laura and her self-destructive streak.
24. Cat’s in the Cradle by Harry Chapin
This song may have fallen into a parody of itself, but it retains the power to make you cry when the mood is right. Chapin’s song tells the story of a father too busy to spend time with his son. Later in life, the father has stopped working and the roles are reversed as he desperately tries to spend time with his adult child. A true tearjerker.
25. Tears in Heaven by Eric Clapton
Tragedy and great songwriting go hand-in-hand. Eric Clapton’s son fell to his death from a New York apartment block at the age of four and inspired this tribute. There have been several versions of Tears in Heaven, which Clapton believed would fade into obscurity after being recorded. The song topped the charts and swept the awards ceremonies in 1992.
Next: Best songs about family ever created
26. Jolene by Dolly Parton
A karaoke favorite, Jolene is a sad song about desperately trying to hold onto your boyfriend or husband. Despite the upbeat chorus, Parton pleads with the title character not to crush her dreams by stealing the love of her life.
Next: Best songs about deep dreams
27. I Know It’s Over by The Smiths
The Smiths are a band known for their melancholy outlook on life that has cut through the work of the singer, Morrissey. This classic piece of unhappiness starts with the line, “I can feel the soil falling over my head.”
28. Nothin Gets Crossed Out by Bright Eyes
Bright Eyes have always had a melancholy tint to their songs, which gives their name an ironic nature. This is a song that looks back nostalgically at the past and with fear of the future. The breaking of the voice of Conor Oberst changes the song into a heartbreaking ballad.
29. Something in the Way by Nirvana
When you look back at the life of Kurt Cobain, tragedy and loss were everyday feelings. Something in the Way is the saddest of songs from a band specializing in teenage desperation. Cobain’s early life is depicted in all its sadness.
Next: Best painful songs full of hurt
30. He Stopped Loving Her Today by George Jones
George Jones thought the song was too sappy and cliché to be a hit but recorded it years after he had reached his commercial peak. The country staple has sounded melodramatic in the hands of other bands and singers but Jones gives the story of loss and lost loves a poignant feeling that breaks your heart.
Next: The top country sad songs of all time
31. Landslide by Fleetwood Mac
Stevie Nicks and Lindsey Buckingham transformed Fleetwood Mac into one of the world’s biggest rock bands. Landslide is a quiet meditation on the speed with which life passes us by. Nicks’ vocals are as impressive and heartbreaking as always, with tissues needed when you are feeling down.
32. When the Party’s Over by Billie Eilish
She may have burst onto the pop scene filled with teenage angst and goth swagger but Billie Eilish has grown into a powerful singer-songwriter. When the Party’s Over gives us a glimpse at her talents as an icon of pop music.
33. Angels By Robbie Williams
Former boy band singer, Robbie Williams was failing to establish himself as a solo artist when he released Angels. “When I’m feeling weak, and my pain walks down a one-way street” is a pretty bleak opening to any song. Angels is a popular funeral song in Europe and gives everybody a chance to wallow in misery for three minutes.
Next: The best funeral songs for mom to honor her
34. Under the Bridge by Red Hot Chili Peppers
The Red Hot Chili Peppers are one of the bands that have the power to spark a party in life or to drive you to the tissue box. Under the Bridge will make you cry every time and is about a time when lead singer, Anthony Kiedis felt alone and unloved. A recovering addict, Kiedis gives us a glimpse into the city as a character in his personal story.
Next: The best songs about loneliness of all time
35. Wicked Game by Chris Isaak
Chris Isaak’s song became popular on the soundtrack of David Lynch’s Wild at Heart. The song is personal to Isaak as it details a lost love affair and the cheating that took place in his relationship.
36. Unchained Melody by The Righteous Brothers
Unchained Melody became a staple of these lists following its inclusion in the romcom, Ghost. The Righteous Brothers created a classic ballad that tugs at your heart with soaring strings and heartbreaking lyrics.
37. Yesterday by The Beatles
The Beatles wrote some of the greatest love songs about loss ever written. Yesterday remains a classic song that has the power to tug at your heartstrings. Paul McCartney’s song about a breakup reflects the regret many of us feel after a relationship has ended. Wanting to return to yesterday and do things over is a feeling we can all relate to.
Next: Greatest Beatles songs of all time
38. Morning Theft by Jeff Buckley
Jeff Buckley’s drowning at the age of 30 adds extra layers of poignancy to any love songs he wrote. Morning Theft is a controversial choice because of the problems surrounding his post-humously released second album. The song is about missing friends and feeling isolated.
39. With or Without You by U2
U2 frontman, Bono, was having a tough time with the success of the Irish band when he wrote this classic love song. Bono was struggling to come to terms with touring the world and being away from his wife and children. The song reflects his desire to be with his family and still prove his band a success.
40. I Will Remember You by Sarah McLachlan
Sarah MacLachlan’s song about loss is a staple at awards shows memorial features. The song is sad and wallows in missing a loved one to the extent you will be crying for your lost family members, lovers, and friends.
41. The Dr***s Don’t Work by The Verve
The Verve are often accused of overproducing their songs until they are too sugary to enjoy. Richard Ashcroft is accepted as the leading frontman of his time and gives a stunning vocal to his song about a personal journey through substance use and depression. Ashcroft’s personal demons have become his driving force and this song reflects on the time he lost to this substance abuse.
Next: Best songs about depression of all time
42. Shipbuilding by Robert Wyatt
Not every heartbreaking song needs to be about a tragic love story. Robert Wyatt spins a beautiful story about the loss of men to war in Shipbuilding. A soaring bassline and the fragility of the vocals add up to a heartbreaking song about loss.
Next: Best bass heavy songs of all time
43. Famous Blue Raincoat by Leonard Cohen
Leonard Cohen is the master of melancholy with some impressive songs that can prompt crying. The Famous Blue Raincoat will have you sobbing from its opening bars to the bitter end of the song.
44. Someone Like You by Adele
Adele’s love life has inspired her to become one of the world’s biggest music stars. The story behind Someone Like you is about the loss of a relationship with an older man the teenaged Adele thought she would marry. The failure of her lover to return her love and future dreams has inspired the song that made her name.
45. The River by Bruce Springsteen
Bruce Springsteen is a misunderstood vocalist and songwriter. His song, The River is as powerful today as it was in the early 1980s. Instead of focusing on lost love, the Boss looks at the financial hardship of his protagonist. The harmonica is heartbreaking and will bring on the tears pretty quickly.
Next: The best 80s hits through the decade
46. Mad World by Gary Jules
Gary Jules broke the mold of singers covering classic songs in a slowed-down style. Gary Jules’s version of Mad World by Tears for Fears can break your heart with its quiet sadness. A teenager looks at the world and sees the craziness all around him. This is certainly one of the best cover songs ever done.
47. The Streets of Philadelphia by Bruce Springsteen
The movie Philadelphia brought the problem of HIV/AIDS to Hollywood. Springsteen supplied the soundtrack with a powerful song about losing a community to the epidemic. A live performance in the music video adds extra power to a song that helped change the attitude of the world to HIV/AIDS.
48. Stay With Me by Sam Smith
Sam Smith is a talented songwriter who created the foundation for Stay With Me in less than 30 minutes. The haunting choir is Smith’s voice layered multiple times on the track. Heartbreaking lyrics about breaking up make this a tearjerker from the modern period.
49. The Shadowlands by Ryan Adams
Adams has become a polarizing figure in the last decade but his career hit its heights with The Shadowlands. Adams’s ability to paint a picture with words was never as clear or heartbreaking as it is during this powerful ballad.
50. The Living Years by Mike and The Mechanics
The song by the British band formed by former Genesis guitarist, Mike Rutherford, has become a cliche in the best sense of the word. The lyrics detail the pain felt by the writer, B.A. Robertson, about the death of his father months before his own son was born.
51. Say Something By A Great Big World
Christina Aguilera added her vocal abilities to this song after it had become an online hit. Ian Axel wrote the heartbreaking song and released it to little attention before it became a reality TV favorite.
52. Good Riddance (Time of Your Life) by Green Day
The song may be used as a feel-good ballad about moving on but it was written about a breakup. The song details the feeling of Billie Joe Armstrong about breaking up with his girlfriend.
53. Ben by Michael Jackson
When we want to cry, a feeling of sentimentality is the best option. The young Michael Jackson performed Ben and made us believe in the friendship between a boy and his pet rat. The song was the theme of a movie about killer rats terrorizing a small town.
54. Candle in the Wind by Sir Elton John
Whether you enjoy the version about the death of Marilyn Monroe or the princess Diana song, Sir Elton wrote a classic. The song pulls at your heartstrings and prompts floods of tears every time it is played.
55. Brick by Ben Folds Five
If the saccharine sweetness of some love songs is too much, ben Folds Five has a gentle touch. The song details an abortion and the writer’s feeling of uselessness as the process is completed.
56. Skinny Love by Bon Iver
The song has been a popular one for many artists, but Bon Iver’s version tops the rest. The emotion of the song cascades through the singer’s voice and leaves us all feeling a sense of loss.
Next: The full meaning behind Bon Iver’s “Skinny Love” song lyrics
57. Samson by Regina Spektor
Spektor wrote a song about the loss of power felt by the legendary Samson when he entered into a relationship with Delilah. The biblical elements of the song add to the timeless power of the track.
58. Green Green Grass of Home by Tom Jones
The Green, Green Grass of Home has become a parody for the sweet ballads of death that took hold in the 60s. Tom Jones classic blends his powerful singing voice and soft Welsh speech to create a powerful ballad about loss.
59. Knockin’ on Heaven’s Door by Bob Dylan
The power of Dylan’s song is in placing his words in the mouth of a deputy dying from a gunshot wound. The song has become an anthem for sadness and loss in the 21st-century. Dylan paints a stunning picture of the scene as the deputy calls for his mother to be with him in his last moments.
60. Black by Pearl Jam
Pearl Jam refused to make videos for most of their career and created a powerful brand based on their impressive songwriting. Black explains the feelings of a jilted man for his lost lover. The song maintains its power despite its 90s grunge aesthetic.
61. Teenage Kicks by The Undertones
The Undertones were an Irish band that achieved some success with this track. The legendary DJ and musician, John Peel claimed he cried every time the song was played because of its lyrical content. The loss of teenage innocence is easy to hear in the lyrics of Feargal Sharkey.
62. God Only Knows by The Beach Boys
The Beach Boys were at the height of their Californian surfer phase when Brian Wilson conceived God Only Knows. The song is about the loss of a lover and the feelings of helplessness the writer felt at the time. Several radio stations banned the song as blasphemous upon its release.
63. Maps by Yeah Yeah Yeahs!
Few songs have the emotional power of Maps because of the rawness of the situation. Karen O was in a relationship with fellow musician, Angus Andrew when she wrote the song about being away from her lover. The video features a crying Karen O who was upset about the fact Andrew was late for the video shoot and she would leave on tour directly after the promo was completed.
There are many reasons why you can find the best sad songs and cry at their content. Feeling we have lost something or somebody in our lives can make us feel sad and want to cry along with a favorite artist. Let us know if we missed out on any of the top sad songs ever made!
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As the Head Editor and Writer at Music Grotto, Liam helps write and edit content produced from professional music/media journalists and other contributing writers. He works closely with journalists and other staff to format and publish music content for the Music Grotto website. Liam is also the founding member of Music Grotto and is passionate in disseminating editorial content to its readers.
Liam’s lifelong love for music makes his role at Music Grotto such a rewarding one. He loves researching, writing and editing music content for Music Grotto.