Films with the Most Heartbreaking Use of a Pop Song

Music possesses a unique ability to elevate the emotional resonance of cinema and transform a simple scene into a devastating memory. Directors often utilize popular songs to underscore tragedy or manipulate audience expectations through ironic juxtaposition. A familiar melody can bridge the gap between the character and the viewer to create a shared experience of grief. The following films effectively deployed pop music to deliver some of the most heart-wrenching moments in movie history.

‘My Girl’ (1991) – “My Girl” by The Temptations

Vada Sultenfuss suffers a devastating loss when her best friend Thomas J dies from an allergic reaction to bee stings. The titular song plays during the funeral service as Vada approaches the casket. She becomes distraught because Thomas J is not wearing his glasses and she worries he cannot see without them. This scene transforms a famously upbeat Motown track into a permanent association with childhood grief and the loss of innocence.

‘Toy Story 2’ (1999) – “When She Loved Me” by Sarah McLachlan

Jessie the Yodeling Cowgirl reveals her traumatic backstory to Woody through a poignant flashback sequence. The ballad plays while the audience watches Jessie grow obsolete in the eyes of her owner Emily. Viewers witness the gradual transition from being a beloved toy to a discarded object in a donation box. Pixar utilizes this song to explore deep themes of abandonment and the inevitable passage of time.

‘The Royal Tenenbaums’ (2001) – “Needle in the Hay” by Elliott Smith

Richie Tenenbaum faces a moment of profound despair while standing in front of a bathroom mirror. The acoustic strumming underscores his meticulous removal of his hair and beard. This quiet ritual escalates abruptly as Richie attempts to end his life in a shocking act of self-harm. Wes Anderson contrasts the gentle indie folk track with the visceral imagery of blood and hopelessness.

‘Donnie Darko’ (2001) – “Mad World” by Gary Jules and Michael Andrews

The film concludes with a montage set to a somber cover of the Tears for Fears classic. Characters awaken from their dreams and struggle with the subconscious weight of the timeline reset. The haunting vocals emphasize the tragedy of Donnie sacrificing himself to save those around him. This sequence ties together the complex narrative threads with a pervasive sense of melancholic acceptance.

‘Call Me by Your Name’ (2017) – “Visions of Gideon” by Sufjan Stevens

Elio Perlman sits alone by the fireplace while staring into the flames as the credits begin to roll. The song captures the raw pain of a first heartbreak as tears silently stream down his face. The camera holds on Elio as he processes the news that his former lover Oliver is engaged to someone else. It provides an intimate portrait of sorrow without the need for dialogue or dramatic action.

‘Good Will Hunting’ (1997) – “Miss Misery” by Elliott Smith

Will Hunting finally decides to leave his old life in Boston behind to pursue a future with Skylar in California. The song plays as Will drives his beat-up car down the highway toward a new beginning. This track bridges the gap between his traumatic past and the hopeful uncertainty of what lies ahead. The late singer received an Oscar nomination for this song that perfectly encapsulates the mood of cautious optimism.

‘Trainspotting’ (1996) – “Perfect Day” by Lou Reed

Mark Renton suffers an overdose that causes him to sink literally and metaphorically into the floor. The lyrics play as Renton is dragged into a taxi and rushed to the hospital by his panicked dealers. The ironic juxtaposition of the serene melody with the grim reality of heroin addiction creates a disturbing effect. Director Danny Boyle uses the song to illustrate the seductive but deadly nature of the protagonist’s lifestyle.

‘Eternal Sunshine of the Spotless Mind’ (2004) – “Everybody’s Gotta Learn Sometime” by Beck

Beck covers this song for the closing moments of this surreal romance about erased memories. Joel and Clementine agree to restart their relationship despite knowing they are destined to repeat their past mistakes. The song plays over a looping image of the couple running on a snowy beach. It reinforces the cyclical nature of love and the inevitability of heartbreak.

‘The Graduate’ (1967) – “The Sound of Silence” by Simon & Garfunkel

Benjamin Braddock and Elaine Robinson flee her wedding on a public bus after a chaotic escape. The folk duo performs this hit as the adrenaline of the moment fades into awkward uncertainty. The camera lingers on their faces as their smiles slowly disappear while the other passengers ignore them. This famous ending subverts the traditional romantic comedy conclusion by introducing ambiguous realism.

‘Stand by Me’ (1986) – “Stand by Me” by Ben E King

Gordie Lachance finishes typing his memoir regarding the body as the screen fades to black. The classic R&B track plays while the adult narrator reflects on the friends he lost over the years. The lyrics resonate with the themes of loyalty and the fleeting nature of childhood bonds. It leaves the audience with a poignant reminder that intense youth friendships rarely last into adulthood.

‘Philadelphia’ (1993) – “Streets of Philadelphia” by Bruce Springsteen

The artist wrote this Oscar-winning song to open the drama about the AIDS crisis. The camera follows Andrew Beckett as he navigates the city while suffering from the physical and social toll of his illness. The haunting synthesizer and weary vocals establish the somber tone of the film immediately. This track serves as a lonely anthem for a man facing discrimination and death.

‘Aftersun’ (2022) – “Under Pressure” by Queen and David Bowie

Sophie watches her father dance to this classic rock anthem during their final holiday together. The song is remixed to distort and slow down as the adult Sophie searches for him in a strobe-lit rave. This musical choice recontextualizes the lyrics to highlight the hidden weight of depression her father carried. The sequence creates a devastating contrast between a happy memory and the tragic reality of loss.

‘Lost in Translation’ (2003) – “Just Like Honey” by The Jesus and Mary Chain

Bob Harris whispers an unheard message to Charlotte on a crowded Tokyo street before they part ways. The song swells as Bob walks away and gets into his taxi to head for the airport. The shoegaze distortion and romantic melody capture the fleeting connection between two lonely souls. It provides a perfect auditory backdrop for a relationship that was intense but destined to end.

‘Guardians of the Galaxy Vol. 2’ (2017) – “Father and Son” by Cat Stevens

The Ravagers arrive to give Yondu a traditional funeral in the vacuum of space. Peter Quill listens to this song on his Zune as he realizes Yondu was his true father figure all along. The lyrics about a father imparting wisdom to his son underscore the tragedy of their reconciliation coming too late. This needle drop brings an unexpected emotional weight to a colorful comic book movie.

‘Blue Valentine’ (2010) – “You Always Hurt the One You Love” by Ryan Gosling

Dean sings and plays the ukulele for Cindy while they walk around a neighborhood at night. He performs a rough version of the classic standard while she tap dances hesitantly. This sweet moment of courtship is juxtaposed with the dissolution of their marriage years later. The song becomes a bitter prophecy of how their love eventually turns into resentment.

‘A Star Is Born’ (2018) – “I’ll Never Love Again” by Lady Gaga

Ally Maine performs a tribute to her late husband Jackson at the end of the film. She sings the ballad while flashbacks show the moment Jackson wrote the song for her. The performance transitions from a large concert hall to a private moment of Jackson singing at his piano. It serves as a public farewell and a private declaration of enduring grief.

‘Romeo + Juliet’ (1996) – “Exit Music (For a Film)” by Radiohead

The band wrote this song specifically for the closing credits of this modern Shakespeare adaptation. The music begins to play immediately after the lovers take their own lives. Thom Yorke delivers haunting vocals that build to a desperate climax as the screen fades to black. The track amplifies the tragedy of two young lives wasted due to an ancient grudge.

‘Moulin Rouge!’ (2001) – “Come What May” by Ewan McGregor and Nicole Kidman

Christian and Satine sing this secret love song to each other throughout the film. The reprise occurs during the finale as Satine dies in Christian’s arms after the curtain falls. The song transforms from a promise of hope into a final goodbye between the lovers. Baz Luhrmann uses the pop ballad structure to deliver a theatrical and devastating emotional climax.

‘Jojo Rabbit’ (2019) – “Heroes” by David Bowie

Jojo and Elsa stand in the doorway as the war ends and American soldiers arrive. They begin to dance to the German version of this rock anthem. The song represents liberation and the survival of the human spirit amidst the ruins of World War II. It offers a bittersweet conclusion that acknowledges the loss of innocence while celebrating freedom.

‘The Perks of Being a Wallflower’ (2012) – “Asleep” by The Smiths

Charlie says goodbye to his friends Sam and Patrick as they leave for college. The song plays on a mixtape that Charlie gave to Patrick earlier in the film. The lyrics about singing someone to sleep reflect Charlie’s struggle with his mental health and loneliness. It underscores the pain of being left behind while others move forward with their lives.

Tell us which film song moment made you cry the most in the comments.