Jade Reed
Sometimes we all need a good cry to release built-up emotions. Music has an incredible power to reach into our souls and connect with our deepest feelings.
These tear-jerking tunes span different genres and decades, but they all share one thing in common – they’ll have you reaching for the tissues in no time.
1. Amy Winehouse, ‘Back to Black’
Raw heartbreak echoes through every note as Amy’s soulful voice chronicles the pain of watching an ex return to a former lover. Her distinctive vocal style perfectly captures the hollow emptiness of abandonment. The haunting production mirrors the darkness of grief with sparse instrumentation that leaves her vulnerability exposed.
When she croons “black” in that final refrain, you can almost feel the void she’s describing. Winehouse’s personal struggles lend an eerie authenticity to this track about loss and despair, making it impossible not to feel her pain.
2. Johnny Cash, ‘Hurt’
Recorded near the end of his life, Cash’s cover of Nine Inch Nails’ song becomes something entirely more profound. His weathered voice cracks with the weight of regret and mortality, transforming an already dark song into something devastatingly beautiful.
The accompanying video shows an elderly Cash reflecting on his fading life, creating one of music’s most powerful visual legacies. The stark contrast between footage of his vibrant youth and his frail present hits like a punch to the gut. When he sings “everyone I know goes away in the end,” it’s with the hard-earned wisdom of someone who’s lived it.
3. A Great Big World & Christina Aguilera, ‘Say Something’
The gentle piano intro sets the stage for this devastating duet about the moment a relationship slips beyond saving. There’s something utterly heartbreaking about the quiet resignation in their voices as they acknowledge the end. Christina Aguilera, known for powerful vocals, delivers a restrained performance that makes the emotion even more authentic.
The simplicity of the arrangement leaves nowhere to hide from the raw pain of giving up on someone you love. The repeated plea to “say something” perfectly captures that desperate moment when silence confirms what you already know but don’t want to accept.
4. Bonnie Raitt, ‘I Can’t Make You Love Me’
Raitt’s bluesy, soulful delivery cuts straight to the heart of unrequited love with stunning clarity. The song’s genius lies in its simple truth – you can’t force someone’s heart to feel what it doesn’t. Piano notes fall like teardrops throughout this ballad, perfectly complementing the quiet dignity in Raitt’s voice.
There’s no anger or bitterness, just the profound sadness of accepting reality. The most devastating moment comes in the chorus when she sings about turning down the lights and laying down with someone who’s only there in body. Few songs capture the loneliness of being with someone who’s emotionally absent quite like this.
5. Eric Clapton, ‘Tears in Heaven’
Written after the tragic death of Clapton’s four-year-old son, this song carries a weight of grief that’s almost unbearable. The gentle acoustic melody creates a bittersweet backdrop for lyrics that explore the most unimaginable loss. Clapton’s voice remains steady but vulnerable as he asks if his son would recognize him in heaven.
The controlled emotion makes the song even more powerful – it’s grief contained but not diminished. Knowing the personal tragedy behind the song makes it impossible to listen without feeling the depth of a parent’s love and loss. The question “would you know my name if I saw you in heaven?” remains one of music’s most heartbreaking lines.
6. Sam Smith, ‘Stay With Me’
Smith’s soulful falsetto carries a unique vulnerability that perfectly conveys the loneliness at this song’s core. What makes it particularly sad is how it reveals the emptiness behind a one-night stand – the desperate need for connection that goes beyond physical intimacy. The gospel choir backing adds a spiritual dimension to this secular confession, elevating ordinary heartache to something almost sacred.
When Smith pleads “stay with me,” it’s not just about one night but about the universal fear of being alone. There’s something incredibly brave about admitting neediness with such honesty. The rawness of the emotion makes this ballad resonate with anyone who’s ever felt the ache of temporary connections.
7. Bon Iver, ‘Skinny Love’
Justin Vernon’s falsetto cracks with emotion throughout this indie folk masterpiece about a relationship that’s withering away. The stripped-down production – just voice and guitar – creates an intimate atmosphere that feels like eavesdropping on someone’s private pain. The cryptic lyrics add to the song’s emotional impact, allowing listeners to project their own experiences onto Vernon’s fractured poetry.
There’s something universal in the way he captures the moment when love becomes too fragile to sustain itself. The repeated refrain of “my my my” conveys more emotion than perfectly crafted sentences ever could. It’s the sound of someone trying to process feelings too complex for words.
8. Sinead O’Connor, ‘Nothing Compares 2 U’
O’Connor’s haunting rendition of Prince’s composition remains one of music’s most powerful expressions of abandonment. Her shaved head and intense close-ups in the iconic video strip away all distractions, forcing viewers to confront raw emotion. The sparse arrangement highlights her incredible vocal control as she moves from quiet vulnerability to powerful anguish.
That famous tear rolling down her cheek wasn’t planned – it was genuine emotion breaking through during filming. When she hits the high note on “nothing compares,” it’s like hearing a heart shatter in real time. Few performers have ever been brave enough to expose their wounds so completely, which is why this song continues to devastate decades later.
9. Sia, ‘Breathe Me’
Sia’s broken vocal delivery perfectly embodies the fragility of someone barely holding themselves together. The song builds slowly from piano whispers to orchestral swells, mirroring the overwhelming nature of anxiety and emotional crisis. The lyrics read like desperate notes from someone who needs rescuing from themselves.
When she sings “help, I have done it again,” there’s a weariness that suggests a pattern of self-destruction she can’t escape. The song gained particular emotional resonance as the soundtrack to the final scene of “Six Feet Under,” one of television’s most devastating finales. Its message of needing human connection when at your lowest makes it a powerful anthem for anyone struggling with mental health.
10. Coldplay, ‘The Scientist’
Chris Martin’s gentle piano ballad captures the particular ache of wanting to turn back time and fix a broken relationship. The simplicity of the melody contrasts with the complexity of human connection that the lyrics explore. The backward-running music video adds another layer of poignancy, showing a story in reverse that can never actually be undone.
Martin’s voice carries a perfect blend of regret and tenderness throughout. Most heartbreaking is the repeated line “nobody said it was easy,” acknowledging that despite our best intentions, some things can’t be fixed. The song’s genius lies in how it finds beauty in accepting painful truths about love and loss.
11. Luther Vandross, ‘Dance With My Father’
Vandross wrote this tribute to his father who died when Luther was just seven years old. The simple childhood memories – being lifted onto his father’s shoulders, dancing around the room – become devastating in their ordinariness. What makes the song particularly poignant is that Vandross recorded it while seriously ill himself, adding layers of mortality to his smooth, soulful delivery.
The longing in his voice when he sings about wanting one more dance transcends the specific relationship to touch anyone who’s lost someone they love. The chorus expressing a child’s simple wish – “If I could get another chance, another walk, another dance with him” – captures grief’s most universal aspect: the desire for just one more moment.
12. R.E.M., ‘Everybody Hurts’
Michael Stipe’s gentle vocals deliver a message of universal pain and solidarity that has made this song a lifeline for many. Unlike most sad songs that explore specific heartbreaks, this one acknowledges collective suffering and reaches out a hand to those struggling. The slow tempo and string arrangement create a space for reflection that feels like a musical hug.
The directness of the lyrics – “When your day is long and the night is yours alone” – speaks to anyone who’s felt isolated in their pain. Most powerful is the repeated assurance to “hold on,” a simple but vital message that has literally saved lives. Few songs manage to be simultaneously sad and comforting in such a profound way.
13. Leonard Cohen/Jeff Buckley, ‘Hallelujah’
While Cohen wrote this masterpiece, Buckley’s haunting interpretation transformed it into the definitive version that breaks hearts worldwide. His ethereal voice navigates the complex melody with a spiritual intensity that feels almost transcendent. The lyrics blend biblical references with intimate reflections on love and loss, creating a song that works on multiple emotional levels.
Buckley’s version strips away everything but guitar and voice, leaving nowhere to hide from the raw emotion. The song’s power comes partly from its contradictions – finding beauty in brokenness, holiness in human connection. Buckley’s tragic early death adds another layer of poignancy to his rendering of this meditation on life’s broken hallelujahs.
14. Adele, ‘Someone Like You’
Adele’s powerhouse vocals carry remarkable restraint throughout this ballad about seeing an ex who has moved on. The piano accompaniment remains simple, allowing her voice to convey all the complex emotions of forced acceptance. What makes the song especially devastating is how it captures that particular kind of bravery – wishing someone well while your heart is breaking.
The slight crack in her voice during the chorus reveals the effort behind maintaining composure when confronting loss. The bridge – “Sometimes it lasts in love, but sometimes it hurts instead” – delivers a universal truth with stunning simplicity. Few artists can make pain sound as beautiful as Adele does in this modern classic about letting go.
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