No matter where your heartbreak may lie, be it heartbreak itself, grieving the death of a loved one, or simply feeling saddened, these songs will provide all of the feels. Just make sure that there is always an ample supply of tissues close by!
“Cat’s in the Cradle” was an endearing folky tragedy that resonated deeply with so many because its events were all too real.
1. ‘Nothing Compares 2 U’ by Sinead O’Connor
“Nothing Compares 2 U,” one of Prince’s finest compositions, has touched many listeners with its universal message of heartache and loss. Prince originally gave “Nothing Compares 2 U” to funk-pop offshoot band The Family for their self-titled debut album in 1985 – though their version wasn’t released as a single and it may have faded from history were it not for Sinead O’Connor’s haunting version being available as a single release.
Shuhada Sadaqat, better known by her stage name of Shuhada Sadaqat in Ireland, became an international phenomenon upon releasing her version of “Nothing Compares 2 U” in 1990. Although she did not enjoy an easy life – forced out of Ireland at age eight due to sexual abuse claims against both mother and Purple Rain star – that did not seem to affect her music performance, which was dynamic yet emotive, with powerful vocals that seemed to reach through to people’s souls; her rendition of this song “Nothing Compares 2 U” stood out even more than ever.
Director John Maybury captured O’Connor’s intense performance beautifully in her music video for this song, with director capturing its beauty through director. O’Connor stares directly into the camera as she sings with such earnest conviction that you cannot help but be moved by her performance. Her menacing vocals pair perfectly with haunting piano chords and Booker T organ work to produce an emotive yet melancholic sound which perfectly matched up to O’Connor’s lyrics about time passing us by – making the record an instant hit that topped charts around the world as it’s legacy – Natalie Imbruglia covered it and so has Jackie De Shannon as well!
2. ‘By the Time I Get to Phoenix’ by Isaac Hayes
Miles Davis’ Kind of Blue, James Brown’s Live at the Apollo and Sgt Pepper’s Lonely Hearts Club Band by The Beatles were all groundbreaking LPs that redefined and expanded their genre; so too was Isaac Hayes’ 1969 release Hot Buttered Soul; fans dubbed this record “Black Moses”, marking its release into new territory for soul music after its three-minute single era had come and gone. Hayes sang, played piano, vibraphone and alto saxophone on Hot Buttered Soul while most famous for orchestral arrangements and production style on it’s film soundtrack soundtrack!
Hayes distinguished himself from Memphis Sound counterparts Otis Redding, Johnnie Taylor and Booker T and the Bar-Kays by opting for a distinctive baritone vocal with intimate harmony vocals that were close and intimate with himself. His lush orchestral arrangements of classic Motown hits like “Walk on By” and Burt Bacharach’s “By the Time I Get to Phoenix” left listeners transfixed with its sensuous arrangements and melancholic melodies; his song “Phoenix,” with its 18 minute rendition of Webb’s break up ballad, was an immense hit among his audiences.
Shelby Lynne may not be known as an upbeat singer, but on 2011’s Revelation Road she delivered one of her biggest and best sad songs to date with “Throwaway Song.” The acoustic rendition recounting Shelby Lynne’s fractured childhood as the daughter of an alcoholic father before his eventual suicide is heart-rending, featuring two gunshots as its final punctuation mark – it will leave you sobbing even if you have never experienced domestic abuse first hand – stream it here now to hear Shelby Lynne!
3. ‘Farewell My Love’ by Gladys Knight
Gladys Knight first made her singing debut as a soloist at four in Atlanta’s Mount Mariah Baptist Church Choir at age four, later winning an amateur singing prize on Ted Mack Amateur Hour and creating The Pips with her sister Brenda, cousins Elenor and William Guest as well as Edward Patten; when Brenda and Eleenor left they changed to Gladys Knight and the Pips to reflect her rise as lead vocalist.
Soul legend Gladys Knight uses her signature Pips with devastating effect in this slow, methodical relationship postmortem that examines an affair which quickly fizzled out. Anyone who has come to terms with the fact that not all love stories have happy endings will recognize themselves in Knight’s passionate and moving performance.
Hank Williams’s heartrending lament for lost love is considered one of the saddest songs ever written for country music, with lyrics like: “Every rose has its thorn, every cloud has its silver lining… If given the choice between love and life… Take life.” Its message of pain-filled separation remains poignant today.
Nelson’s sparse rendition is perhaps the most iconic rendition, featuring only acoustic guitar, accordion, and his trademark wounded warble, along with an accordion. The song quickly became an audience favourite because of her poignant delivery and haunting melody; it became an international success thanks to its haunting melody and emotional delivery from singer Gladys Knight who enjoyed both country as well as R&B/soul successes such as having several chart-topping singles such as performing with Dionne Warwick, Stevie Wonder and Elton John at an AIDS research concert held in New York in 1985.
4. ‘Past, Present and Future’ by The Shangri-Las
Growing up during the Sixties likely meant your music library only contained a handful of songs by The Shangri-Las. CDs did not exist yet! Yet their tragic love tragedies are legendary, particularly ‘Past, Present and Future’ by Wendy Rene’s haunting breathy vocals which added even further chill to this tale about an unfaithful wife taking their lover to her grave with her.
Heavy doesn’t begin to describe Shelby Lynne’s emotional and captivating acoustic ballad Revelation Road from 2011. Shelby recounts the 1986 murders of both of her parents before they committed suicide; this track contains enough pathos for an entire Lifetime movie in its first two minutes alone! Alison Krauss adds her signature sophistication, further elevating it all.
Anybody who thought Radiohead had reached its maximum level of melancholy with OK Computer was in for an unexpected shock three years later when Kid A revealed an ocean of electronic melancholy they hadn’t even begun exploring yet. Kid A’s sparse track “Hope is Lost”, with its mournful synth drones and haunting piano motif is Radiohead at their most heartbreaking. Not just mournful over someone they lost close, it speaks more generally about a world gone mad with despair.
5. ‘Fatalism’ by Otis Redding
Country star Tammy Wynette made headlines in 1986 for her bitter divorce from husband Don Henley and wrote an emotionally wrenching ballad that has since become the standard in such songs. Acoustic retelling of their fractured home life — including him shooting both of them– is so gripping, you can almost feel the gunfire crackling around you.
Redding’s death was tragic, yet his legacy lives on in his remarkable catalogue. His 1963 debut on Stax Records stands out as an outstanding example of soul auteurism; Redding’s voice responds to every instrumental note to build towards an intoxicating crescendo that makes for unforgettable listening.
Lyrically, Redding’s song remains vague but some believe its inspiration came from his move from Macon, Georgia to San Francisco in search of new opportunities. Fresco Bay could represent yearning or hope of something just out of reach.
This posthumous #1 hit serves as a heartrending reminder that, although happiness may exist now, misery always follows us wherever we go. With its haunting vocal hook (later sampled by Wu-Tang Clan) and muted Booker T organ work, this track remains one of Booker T’s finest works and remains timeless classic.
Though the narrator in this haunting tale of doomed love and an awful car accident is never named, it is evident that she will take this secret with her to her grave. The Shangri-Las were responsible for several teenage tragedies in the 1960s; one such tragedy featured an emotional harrowing tale set to Beethoven’s Moonlight Sonata that earned them their only top ten hit on Billboard Hot 100.