Heartbreak is an experience unique to each of us; no two stories about it are the same. From country dramas to psychedelic melodrama, there are songs galore that capture its relentless grip.
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Sinead O’Connor’s ‘Nothing Compares 2 U’
Sinead O’Connor achieved iconic and heartbreaking one-hit success with “Nothing Compares 2 U,” already an influential critic and college radio staple at the end of the ’80s; O’Connor shot into the top 10 of Billboard Hot 100 chart hits thanks to this Prince song which ended up becoming her sole chart hit.
Produced and engineered by Nellee Hooper and Chris Birkett, this version of “Lean on Me” by Sinead O’Connor features sparse arrangements which allow her voice to shine brightly despite its saccharine lyrics – creating an unforgettable performance by O’Connor that remains one of her most iconic performances ever.
At the time of its recording, O’Connor’s relationship was in disarray, perhaps explaining her abrupt and dissonant interpretation of this song. Her rendition is coldly confrontational in its verses while its chorus almost stomps along to emphasize her desolation words. O’Connor’s authenticity – one of her defining features as an artist–is what makes this version memorable; its lack of compromise ensured her tragic fate within pop music history. Her refusal to play nice and read the room ultimately doomed her.
Townes Van Zandt’s ‘By the Time I Get to Phoenix’
Van Zandt’s songs paint vivid pictures with words. Whether he was talking about a dive bar poet, cowboy fanatic or just someone passing along the roadside with furrowed brows he could make us feel as if we were there too. A master storyteller with poetic flair and limitless talent he captured the grittier sides of life with unparalleled talent and beauty.
This song tells a simple yet captivating tale of one man leaving his lover for Phoenix, Albuquerque and eventually Oklahoma. Written in 1972 but still relevant today; anyone who’s experienced heartache will relate.
Steel strings twang against the beat of a box drum on this song by Van Zandt. His soft voice floats gently over an acoustic backdrop while his gentle tenor perfectly complements its somber lyrics – truly classic material if there ever was one! A beautiful yet melancholy tune that speaks to anyone searching for their place to call home.
Shangri-Las’ ‘Past, Present & Future’
The Shangri-Las were four high school girls plucked from anonymity by record industry, thrust into an intense touring and publicity schedule and given hits including “Leader of the Pack.” On-stage performers could see them dancing along to lyrics while wearing daring skintight leather pants and boots that made an impressionful statement about life at that time.
Though relatively young, they were extremely mature for their ages and had a powerful vocal harmony. “Remember (Walking in the Sand),” their first hit single released shortly before embarking on their first tour to England was written and recorded shortly beforehand.
This track was unique because there were no actual musical instruments present during its recording. Mary Weiss spoke eerie words of an undying sorrow from her past that left her uncertain for the future, while the rest of the band supported her voice by using spoken chants as backing music – creating an eerie yet haunting effect which was further amplified by using near-classical music, an unusual choice at that time for girl groups.
Dolly Parton’s ‘It’s Wintertime’
Dolly Parton’s 20th century bluegrass album Little Sparrow immediately stands out due to her vibrant onstage performance. Recorded at Dollywood, in this live track she turns into a burlesque singer before unleashing some fierceness (“It’s wintertime/And the devil is taking over my body!!”). Supported by Alison Krauss and Dan Tyminski on harmony vocals as well as A-list players like Chris Thile on banjo and fiddle, Parton displays both humor and anguish at once!
Coat of Many Colors remains her signature song, yet this early rendition of “My Blue Tears” really packs a powerful punch. Boasting an unmistakably country sound with its twangy acoustic guitar sound and its heartbreaking, crackled voice of Dolly Parton, this is country music at its purest form – authentic country that won’t let any filters interfere.
Parton’s most straightforward song, this piece shines the light on lyrics that read like a film script. The protagonist finds herself heartbroken by an impoverished lover but manages to maintain her defiant attitude by attending a party two doors down where she finds Mr. Right Now. Over time, its interpretation has seen numerous different takes, from Esther Williams and Ricardo Montalban duetting it together for Rhinestone (1948) all the way through to Blaine Anderson and Kurt Hummel singing it together on Glee (2010)!
Bob Dylan’s ‘Boots on the Ground’
Bob Dylan is one of the world’s best-known singer/songwriters, known for his poetic lyrics and revolutionary approach to music. First making waves as a folk singer in Greenwich Village during the early 1960s, his music has touched people worldwide; songs like “Blowin’ in the Wind” and “The Times they Are A-Changin” became anthems for generations – setting new standards in lyrical writing.
This song tells the tale of a traveller asking their beloved for something to remind him of her on their journey homeward. Unfortunately, they receive only responses that state what she really desires is for their reunion instead of material reminders. Thus leaving the narrator sad and doubting their return.
Dylan returned to performing and album releases, including Highway 61 Revisited, Blonde on Blonde, Blood on the Tracks and Slow Train Coming. Inducted into the Songwriters Hall of Fame in 1982 and receiving a Grammy award for Time Out of Mind 1997 album; awarded Presidential Medal of Freedom 2012 as well. Dylan has also published books and shown his art exhibitions around the world.
Otis Redding’s ‘A Change is Gonna Come’
Otis Redding was an influential soul singer who was deeply moved by the social unrest and discrimination taking place at that time. To bring about change he wrote this song as a call-to-action for African Americans – his rendition being one of the most moving and powerful ever heard, rivaled only by Aretha Franklin’s.
While both versions of the song are emotional, Redding’s version was recorded just months before his tragic plane crash death in Madison, Wisconsin. He and his band had just left home when their plane suddenly went down four miles short of reaching its airstrip en route to a show there.
Redding’s tragic passing left behind an enduring musical legacy that still resonates today, such as his version of “A Change is Gonna Come” which reminds us all that we deserve a society free from oppression and discrimination; therefore we should work towards that goal, never giving up hope that injustice may one day end soon. His rendition features lyrics such as: “Swing low sweet chariot, coming for you”, reminding us to never lose hope that justice may prevail one day soon.
The Cure’s ‘Enjoy the Silence’
Few music acts have made such an in-depth examination of sadness than The Cure. Right from their debut album, this band balanced darkness with hopelessness to create their signature sound – and likely contributed to their longevity over two decades later.
Through Faith’s sorrowful pain to Violator’s personal catastrophe, this band captured some of life’s deepest sadnesses through music. Their signature style can still be heard on Bloodflowers – their latest album release.
Utilizing the same chord progression as Enjoy the Silence, this song begins with a dark two-chord vamp repeated throughout and then an unexpected minor chord switch to add tension and gloom – something often employed by this group on songs like Shake the Disease and Embrace. Lyrically, it depicts romance collapsing amid mixed feelings ranging from spiteful anger to regretful longing.
Depeche Mode approached Anton Corbijn to direct their music video for “King”, featuring Dave Gahan in the style of a medieval king exploring beautiful countryside locations all across Europe dressed like royalty – an approach which perfectly captured its message of lost innocence and blind hope.