No matter if it was your initial shallow heartbreak or trying to reignite an old flame, these ’90s sad songs offered you solace. From haunting a cappellas to epic orchestral ballads – here are the best of them all.
Culturally, 9/11 marked the initial bookend for this decade; Kris Klosterman believes the song that most encapsulates it is Nirvana’s Nevermind.
Frank Ocean
Frank Ocean first made waves in the ’90s with soulful breakup songs that brought tears to many listeners, yet his self-titled debut album remains his greatest achievement, featuring its dark tale of heartache and suicide – perfect for listening while driving alone at night.
Tori Amos has made a career out of singing about heartbreak, and Tear in Your Hand is her signature anthem for it. Boasting an entrancing earworm vocal hook and an air of melancholy piano notes that resonate so profoundly it seems almost tangible, Tear in Your Hand’s appeal lies in its nostalgic lyrics as much as in its haunting melody and haunting piano work that conjure up memories of lost loved ones.
The Cure’s darkest album was 1989’s Disintegration, and this epic track captures its entire mood perfectly. The lyrics capture a relationship becoming irreparably broken down; no wonder people love crying to it! A classic cover by both Natalie Imbruglia and Psychic TV have also covered it successfully; though Sinead O’Connor stands out with her emotive vocal performance and emotive synth strings – these tracks have since been covered by other artists like Taylor Swift or Adele.
Tori Amos
Tori Amos earned one of the most dedicated followings in music with her exquisite piano prowess and mezzo soprano voice, garnering her an instant classic record with 1992’s Little Earthquakes album. Though Amos explored new avenues musically through later efforts such as Boys for Pele, her distinctively emotive lyrics remained at the heart of her work.
While the ’90s had their share of ballads, few inspired late night bedroom sob-alongs quite like this one by Philly soul group House. Their a capella cover of an obscure Motown song caused tears to flow for fans worldwide; its heartache-inducing lyrics have since been covered by many artists including Natalie Imbruglia, The Corrs and even Psychic TV!
In the 1990s, Amos began exploring more social issues and American politics through her music. Her 1999 album Native Invader explored this territory to great critical acclaim, while in 2001 she released Strange Little Girls; an attempt at reinterpreting male artists’ work through female eyes; this even resulted in creating a website to support this effort which donated proceeds to RAAN (Rape Abuse and Neglect National Network). Amos continued releasing music up until 2022.
Sarah MacLachlan
Sarah MacLachlan, an intimate Canadian singer-songwriter renowned for her intimate voice, honed her craft by taking lessons in voice, classical piano and guitar. After making her first mark as front girl for a new wave band before Nettwerk Records offered her a solo deal in 1987 – though initially reluctant, McLachlan ultimately accepted and moved to Vancouver to begin recording albums for them – since which she has earned numerous Grammy and Juno awards with over 40 million albums sold globally.
She has become famous for her emotive songs of heartbreak and loss, such as “Last Dance.” Additionally, audiences were dazzled by “Sweet Surrender,” a touching ballad depicting depression-prone woman contemplating suicide.
Tori Amos made her career out of singing heartbreak songs, such as her powerful rendition of Leonard Cohen’s classic, which depicts a woman going through an excruciating divorce. No surprise then that this powerful rendition is still popular today among those experiencing pain; especially at times of sadness it helps knowing we have artists like Tori Amos to help sing us through.
The Verve
The Verve was one of the most iconic rock bands of the 1990s, yet their songs weren’t all upbeat and joyous. Some were extremely melancholic; for instance “History,” written about love and loss as well as Ashcroft’s breakup with his partner at that time, has an emotionally charged melody which will put listeners in an introspective state.
This tearjerker song features an exquisite piano melody. The lyrics speak about lost dreams and grieving loved ones – making this an emotional track which may cause you to cry as it prompts self-reflection on life itself.
Tori Amos may have been known for her heartbreak-themed songs in the 1990s, but The Verve were one band who took it a step further. Their 1997 album Urban Hymns became a massive success and made their song “Together Again” an instant classic; yet its lyrics later proved to have been borrowed from Andrew Oldham Orchestra’s 1965 version of Rolling Stones’ “The Last Time”.
Richard Ashcroft
No matter the situation – be it long distance relationships or trying to reignite old flames – nothing beats music as a form of therapy. From ballads and confessionals, there is an array of tearjerking tunes out there which will help you to overcome difficulties and work through them more quickly.
Tori Amos made her name singing about lost loves and broken hearts, with this masterpiece standing as one of her signature works. A piano, weeping synth strings, and her exquisite voice come together to evocatively convey grief and heartache in this haunting piece of work.
Sorry that Sinead O’Connor didn’t make our list – she recorded an unforgettable and heart-wrenching rendition of this sad, mournful classic with beautiful vocals that will haunt your dreams and heartbreak you at once! Her version has an almost hypnotic slow tempo which only deepens its impact when singing about tragic love stories or painful losses; also in 2021 as part of Songs of Sorrow and Love album it makes it an essential listen. Don’t miss it!
Robert Wyatt
No matter the situation, nothing beats listening to an emotionally stirring sad song to put things into perspective. Luckily, the 1990s offered up plenty of choices from Tori Amos’ heartbreak ballads to Hanson’s heartbreaking breakup tracks; here are 10 songs you just can’t help but cry along to.
Cocteau Twins frontwoman Chantal Kreviazuk gave a dramatic and spine-tingling performance on her debut solo album with this haunting song featuring haunting melodies that are just as effective in their simplicity as they are with poetic lyrics. This tale tells how one man lost their love to a world beyond their reach, with her restless voice emphasizing this impression that it may already be too late for them to return home together again.
This track features an ominous piano accompaniment to create its sombre atmosphere, but isn’t about death but instead laments hopelessness – making for a fitting conclusion to an album which wasn’t an instantaneous success. Thanks to poet Michael Horowitz’s efforts however, Soft Machine found new audiences through Daevid Allen Trio’s appearance at ICA in 1963 alongside jazz pianist Stan Tracey and Beat Generation novelist William Burroughs (both future Soft Machine members).
Leonard Cohen
Leonard Cohen’s music wasn’t solely about sadness; rather it explored the questions behind love, sex, war, religion and death – often flushing them away with drugs or alcohol before starting again – always emanating with some form of wisdom.
“Tonight Will Be Fine” by Don Henley is one of his more straightforward works, showing that sometimes poetry lies in how its words are delivered. With its haunting melody and subtle Booker T organ work from Songs From A Room album, this powerful statement about human suffering sends out a strong message about futility of human pain.
It’s hard to think back on the ’90s without hearing at least one sad song, whether from rejection or fear. These cathartic tracks helped many young people cope during their formative teenage years – from Frank Ocean’s Swim Good and Tori Amos’ Tear in Your Hand being timeless examples; each sad tune reminds us that heartache should not be hidden away but accepted openly, thus cementing their legacy forever as reminders that heartache should never be shamed or hidden away; their poignance makes them truly unforgettable.