Whatever it is you are mourning, nothing beats a classic sad song to bring tears of heartbreak and despair to mind. So sit back and let these classics transport you on their musical journey of heartache and sorrow.
Master these songs by listening closely to their lyrics, paying close attention to tempo, melody, and chord progressions.
1. Shipbuilding by Robert Wyatt
An expert music lover always has the ideal playlists ready, such as workout music to get in the zone for exercise, party playlists that encourage everyone to hit the dance floor and of course sad songs – such as this spine-tingling ballad from Townes Van Zandt when feeling down or emotional. When listening to this tune from his early career, Townes tells his girlfriend she must travel on without him before telling her what he wants most for his return: that his greatest wish is for her safe return home.
The lyrics of “Soft Machine’s Lament for London” are delicate and tender – an antidote to Elvis Costello’s usually tough-talking approach at that time. Instead, Robert Wyatt – drummer and vocalist for Soft Machine – gives this track its poignancy, rendering the tune one of Britain’s more touching releases during its macho period.
An earworm melodie and some muted Booker T organ are enough to convey the depths of despair and heartbreak, with this song covered by artists as diverse as dance-pop troupe Saint Etienne (who released their version in 1991) to Natalie Imbruglia, The Corrs and Psychic TV – but Wyatt’s restrained delivery stands out from among all these different renditions as truly beautiful and moving sad songs; making this timeless classic an all-time great!
2. The Famous Blue Raincoat by Leonard Cohen
Leonard Cohen is known for writing lyrics with deeply emotive and heartbreaking themes, such as this song from 1971. Written about an emotionally distraught man (Jane), who feels betrayed by their friend FBR – who took Jane away to the desert for some time – which left Cohen feeling guilt-ridden and empty inside; formal meter is employed here effectively by using Amphibrach’s long syllable, followed by two short ones on either side – to convey pain and anguish; particularly during this song!
If this song were written by any other songwriter, its meaning would be clear. Unfortunately, Cohen is a poet and does not reveal all of FBR’s story in this song. Perhaps FBR was an honourable man with high social standing who loved Jane deeply but could not come to terms with her deceiving him and taking advantage of their relationship.
This haunting and melodious tune features piano and guitar accompaniment for its haunting melody, telling a sad and beautiful tale about love, loss, betrayal and life itself. This track also offers us insight into dealing with life’s difficulties while at the same time reminding us to cherish every moment as life continues its course – making this song ideal for listening when feeling downhearted. Part of Here It Is: A Tribute to Leonard Cohen album featuring legendary performers Norah Jones, Peter Gabriel, Gregory Porter Sarah McLachlan Luciano Pavarotti among others!
3. The Greatest Love Story Ever Told by Paul Simon
Paul Simon has enjoyed a distinguished career spanning decades, from his folk rock collaboration with Art Garfunkel to melancholic solo albums. But perhaps his finest moment may have come at the very end: in 1983’s single ‘The Coast’ from his ambitious follow-up Graceland follow-up The Rhythm of Saints album he explored pop vocal sound at its pinnacle: from English folk melodies through to Andean mountain music-influenced pipes and vocal harmonies before finally masterfully producing this symphonic production.
This song captures an astute observer of human existence and turns it into an emotionally wrenching piece. A lover leaves her lover behind to travel home to Africa while the former wonders whether she’ll ever return – she tells him she won’t, but will miss him all her days; her last line “I’ll miss you all my days” can bring on tears.
If you have ever lost someone close to you, this sad song will strike a chord in you. Written to remember loss and pain while simultaneously celebrating life itself. Even if it hits hard without personal experience of loss or sorrow attached, its words make the reader feel seen and acknowledged by its author.
Townes Van Zandt was known for crafting some of country music’s most emotional ballads. From outlaw tragedy ‘Pancho and Lefty’ to folky melodrama of ‘Tecumseh Valley’, his works captured our hearts like none other. One such heartbreaking tune from Townes is “Old Fashioned Tale of Hardship Cruelty Addiction”, in which Van Zandt’s voice swells and crackles with emotion as strings and horns build in one minute resolution that is both moving and moving at once!
4. I’ll Be There for You by Elton John
Every music lover needs playlists for every situation: workout playlists, party ones and of course one for when life doesn’t seem to go as planned – or when emotions just aren’t flowing smoothly. A sad song playlist can provide comforting songs during times of strife or emotional struggles; having one helps us manage through tough times!
Elton John is an iconic figure and some of his albums may not have been his finest work (even though he would probably admit as much himself), but he did produce some beautiful tunes such as this slow ballad that shows emotion through Elton’s vocal performance. It was even recorded again for charity albums shortly after 9/11; specifically Concert for New York City album.
Elton and Bernie Taupin worked together on this version, creating lyrics jointly. Additionally, this hit marked one of his first big successes as a composer.
Elton made his first collaborations with producer Gus Dudgeon and arranger Paul Buckmaster – both would become essential components in his future works.
Your listen can hear Elton and Bernie’s musical influences shine through, especially the strings and piano playing, in this breathtaking track that will leave you speechless with its beauty and emotion. While overplayed on radio stations, this gem should still feature in any music lover’s collection; indeed it was one of Elton and Bernie’s biggest hits together, helping build their careers together.
5. The Greatest Love Story Ever Told by Cyndi Lauper
Every music lover needs an ideal playlist for every circumstance — workout songs, party tunes when your friends can’t stop dancing and a sad song list. No matter whether it be through heartbreak, missing your significant other or simply experiencing feelings of melancholy; having music that resonates can make all the difference in mood-boosting effects.
Cynthia Ann Stephanie Lauper was born and raised in Queens, New York where she began writing her own material as early as age 12. She quickly distinguished herself by dressing differently and often dyeing her hair; dropping out of high school at 17 to escape an abusive stepfather; and starting performing in local cover bands while using singing lessons to develop an iconic singing style that she continues today.
She has long been known as an accomplished mother, gay rights activist (she founded the True Colors Fund), and international performer; all while continuing to release albums at the top of the charts. Additionally, in 2012 she published her bestselling memoir True Colors: My Journey into Pop.
But Lauper’s most compelling and moving track may be her slow-burning ballad “Time After Time.” A ticking drum machine, burbling synthetic bassline, processed guitars and synthesizers and an abundance of sustain on keyboards create the foundation for Lauper’s soulful, emotive chorus which ranges from contemplative murmurs to full-on belting out lyrics with her signature “I’ll be wayyyy ting.” Lauper has since covered this song numerous times – dance-pop troupe Saint Etienne covering Lauper’s original still rings true today. Saint Etienne covered this track as have singer Natalie Imbruglia and Psychic TV. Her version still rings true!
An emotionally engaging song doesn’t owe its emotional impact solely to its melancholic composition; oftentimes it recalls tragic episodes from our own lives that move us emotionally. This holds true in other forms of art as well, from Shakespearean Hamlet and Picasso’s Guernica.
Damon Albarn ditched his typically confident demeanor for this slow, deliberate relationship postmortem. His butter-rich voice soars majestically up and down octaves to convey heartbreaking lyrics about lost relationships.
1. ‘Enjoy the Silence’ by Basildon
Have you experienced the heartbreak of a bad breakup? Depeche Mode’s 1990 hit ‘Enjoy the Silence’ is an emotionally raw yet heartrending ballad about ending relationships; it became their first top ten single in UK since ‘Master and Servant’; today it remains one of their most beloved songs.
Music of This Liar by Dave Gahan is an emotive, mournful lullaby with its bassline pulsing like a heartbeat and vocals of resignation to life’s sorrows delivered by Dave Gahan’s vocals. Its melodic beauty and powerful lyrics have made this track a mainstay of many sad playlists; Natalie Imbruglia, The Corrs and Psychic TV have covered it among others; Mike Shinoda of Linkin Park even remixed it on their remix album Remixes 81-04!
Anton Corbijn’s mesmerizing video for “Kill The Power” by Depeche Mode conjures up images from The Little Prince by Antoine de Saint-Exupery, showing Gahan traversing Scottish Highlands, Portuguese coastline and Swiss Alps with beautiful visual imagery that beguiles and disproves any criticism leveled at Depeche Mode’s ability to write from their hearts or craft memorable melodies. This powerful work sends out a clear message: Depeche Mode can write from their hearts or compose unforgettable melodies!
Human voice was judged the most frequently used instrument to convey feelings of sadness, followed by acoustic guitar and piano. Cello, violin and viola rounded out the top five while triangle, wood block and tambourine were least frequently seen as producing that emotion. This chart is derived from data gathered through a public survey of 44 instruments.
2. ‘By the Time I Get to Phoenix’ by Glen Campbell
Few sad songs capture the depths of sorrow quite as beautifully or poignantly as this country ballad. It tells of a man coming to terms with losing his beloved partner forever, complete with emotive vocals, strings and piano invoking feelings of loss and despair reminiscent of its cover by Natalie Imbruglia, The Corrs and Psychic TV – three artists which have all recorded covers for it!
Jimmy Webb composed this heartbreak song in 1967, but Glen Campbell is responsible for its most well-known recording. Campbell performed it with emotion and skill crooning it while playing baritone guitar (he had already established himself as a session musician by this point). It is an emotional anthem and classic piece of music with many layers.
Robert Smith from The Cure’s 1989’s Disintegration album does not do light and breezy, and this haunting track from it proves it. A serpent-like eight-minute song that snakes between mournful piano chords to paint a dark picture of relationship breakdown – both beautiful and heartbreaking at once; an experience to treasure and remember forever.
3. ‘It’s Over’ by Sinead O’Connor
Sinead O’Connor has long been one of pop music’s most divisive figures. Her reputation as an outspoken spiritual radical and fierce feminist set her apart, even during the height of her popularity in 1992. She was an artist whose music touched upon the depth of human suffering with lyrics that cut through rock sentimentality, as well as a voice that could make your spine tingle. She denounced racism, championed abortion rights in Ireland and made waves when speaking out against powerful institutions on Saturday Night Live. O’Connor famously sang Bob Marley’s “War” during an a capella rendition and tore up an image of Pope John Paul II as she declared, “Fight the real enemy,” meaning institutional child abuse in the Catholic church. O’Connor carried out her words by taking direct action against it – by tearing a photo from Pope John Paul II during an a capella rendition in response to what she perceived was its prevalence in society at large.
O’Connor went on to release several powerful protest albums, such as ‘Nothing Compares 2 U.’ This song featured both contemporary sounds and deep sadness; making it an immensely successful hit for this Irish artist who first burst onto the UK scene three years prior to its release. O’Connor refused to back down from any controversy she encountered and ensured this song became one of the most iconic sad songs ever.
Saint Etienne released a jazzier rendition in 1991, yet its original remains a heartrending song of loss and yearning that has been covered by several artists, from Natalie Imbruglia to Psychic TV. The narrator seems resigned to more than momentary heartache while the piano’s mournful waltz adds haunting beauty.
4. ‘Endless Love’ by Michael Bublé
No matter the situation, these stunning love songs provide hope and solace for anyone seeking relief from broken hearts or reinforcing long-term commitment. A timeless classic that conjures feelings of longing and melancholy, “Pilgrimage” has been covered by artists such as Natalie Imbruglia, The Corrs, Psychic TV – its soothing melody and piano chords perfectly capture an unfulfilled desire.
Dolly Parton first wrote this song, but Whitney Houston made it legendary through her powerful vocals which capture the profound emotions of eternal love and loss. Titanic helped further popularize it as an iconic romantic melody of all time.
Michael Buble has long been known for redefining smooth jazz, and this song from his album Crazy Love exemplifies this trend. With his soothing voice and light instrumentals creating an uplifting atmosphere of hope for those still searching for their soulmate, Crazy Love provides hope to anyone seeking true love.
Robert Smith of The Cure is not known for being particularly cheerful; but when writing this mournful break-up ballad for their 1989 masterpiece Disintegration he was particularly melancholic. For four and a half minutes the song features ambient synths, introspective vocals and pitiless eyes as it explores relationship breakdown.
From romantic ballads from the 1950s to modern club bangers, there have been no shortage of songs inspired by love in Hot 100 history. We have selected our favorites ranging from classics to contemporary hits that capture its emotional journey.
5. ‘Stay With Me’ by Mariah Carey
Carey’s take on breakup songs was unlike anything seen before in pop eras: hers was one of yearning, hope, and loss, with beautiful yet haunting lyrics and melody, raw emotion in its vocal performance, weeping synth strings, tearful video footage… all adding up to become one of the most successful (yet tragic) tracks ever in musical history.
Mariah Carey is an award-winning American singer-songwriter-record producer-actress-philanthropist known for her five-octave vocal range, power, melismatic style and use of whistle register. Additionally, Mariah Carey is known for her extravagant lifestyle including signature costumes and makeup usage.
Stay With Me is Carey’s first single from her fifth album Fantasia and an emotive ballad of desperation and unrequited love, earning top ten status in over twelve countries worldwide. A deeply moving song that perfectly showcases why Carey is widely considered one of music history’s premier performers.
Carey mourns her dream of finding someone with whom to spend eternity; yet, this fantasy will likely never become reality. The song has been described as haunting; while its accompanying music video beautifully conveys the heartbreak and pain associated with losing someone dear to one.
Since November 1994, this iconic holiday track has spent every Christmas since its release at the top of the US Billboard Hot 100 chart. This success made it the second-longest-running number-one single ever and set a record for most weeks at number one for female artists.