10 Sad Songs That Will Always Make You Cry (2024)

Feature Photo: Krists Luhaers

There are sad songs, and then there are songs that transcend sadness to strike directly at the heart of listeners, songs that elicit such a deep emotional response that they almost feel like personal experiences. These are songs that connect with people in a way that goes beyond the notes and lyrics—they resonate because they capture universal feelings of loss, love, and longing in the most raw and honest forms. These ten songs don’t just evoke sadness; they bring forth waves of emotion that lead countless listeners to tears time and again.

Take Dan Fogelberg’s “Leader of the Band,” a heartfelt tribute to his father, which taps into that deep connection between a child and a parent, making anyone who has lost a father feel both comforted and broken. George Harrison’s “All Those Years Ago,” a loving tribute to his late friend and bandmate John Lennon, stirs memories of shared joy and loss, capturing both personal and public grief. “God Give Me Strength,” the powerful collaboration between Elvis Costello and Burt Bacharach, expresses the raw desperation of heartbreak in a way that is universally relatable.

Billy Falcon’s “Heaven’s Highest Hill” painfully captures the unimaginable grief of explaining the death of a loved one to a child, while Kate Bush’s “Wuthering Heights” takes the ache of unrequited love and loss straight from the pages of classic literature into an ethereal musical experience. Yaz’s “Midnight” pours out regret and sorrow, reflecting on mistakes that led to a deep emotional loss, while Ambrosia’s “How Much I Feel” explores the bittersweet pain of realizing you’ve loved someone who will always haunt your heart.

“Father and Son” by Cat Stevens frames the universal generational divide, revealing the aching struggles of understanding between a parent and a child. Henry Gross’s “Shannon” tenderly commemorates the loss of a beloved pet, turning what might be a small, personal tragedy into something deeply relatable for anyone who has lost a dear companion.

As we move through this list, one thing becomes clear: these are not just songs that evoke sadness; they are songs that invite us to reflect on our own lives, loves, and losses. They are songs that always bring tears, not because they are simply sad, but because they express emotions that are part of the human condition, in ways that are beautifully, achingly real.

# 10 – One Less Bell To Answer – The 5th Dimension

“One Less Bell to Answer,” performed by The 5th Dimension, is a timeless ballad that captures the deep sorrow of loss and the emptiness that lingers afterward. Released in 1970, the song was written by the iconic songwriting duo Burt Bacharach and Hal David, known for their emotionally charged lyrics and lush, sweeping arrangements. The song was included on The 5th Dimension’s album Portrait and became a major hit, peaking at number two on the Billboard Hot 100. The track was produced by Bones Howe, and it features the group’s trademark harmonies, anchored by the powerful lead vocals of Marilyn McCoo.

Recorded at Wally Heider Studios in Los Angeles, the song exudes a melancholic elegance, driven by Bacharach’s intricate orchestration. McCoo’s haunting delivery elevates the heartbreak in the lyrics, where every note resonates with the pain of unrequited love and abandonment. “One Less Bell to Answer” tells the story of someone grappling with the absence of a loved one, symbolized by the simple but devastating metaphor of a bell that no longer needs to be answered. The song’s quiet strength lies in its simplicity—each verse slowly unravels the depth of the narrator’s grief, punctuated by the recurring line, “One less bell to answer, one less egg to fry.” The mundane becomes unbearable as the daily reminders of what was lost are magnified.

Lyrically, the song explores the all-encompassing nature of grief and the struggle to move on when someone has left. McCoo sings, “Why, why did he leave? Now I’ve got one less egg to fry,” expressing how even the smallest tasks become burdensome when you’re left alone. The song expertly captures that moment when loss turns from acute heartbreak to a quiet, persistent ache, showing how absence reshapes everyday life in the most painful ways.

This song, as the opening entry on the list of “10 Sad Songs That Will Always Make You Cry,” sets a powerful emotional tone. It dives deeply into the human experience of longing and loss, demonstrating that sadness isn’t always about the dramatic moments of grief, but rather, the subtle, relentless reminders that remain. “One Less Bell to Answer” resonates for its simplicity and its ability to capture the universal feeling of being left behind. As we explore other songs on this list, the theme of love lost and the sorrow that lingers will continue to be a thread, but this song’s quiet power lays the foundation for what is to come.

Read More: Top 10 Fifth Dimension Songs

# 9 – Heaven’s Highest Hill – Billy Falcon

Oh my God, I started crying as I was starting to write this while listening to Billy Falcon sing those words “Love Dont Stop.” This one is really tough to listen too. “Heaven’s Highest Hill,” performed by Billy Falcon, is one of the most deeply personal and heart-wrenching songs from his 1991 Pretty Blue World album. This track was born out of immense tragedy, as Falcon wrote it in the aftermath of losing his 29-year-old wife to breast cancer. The song not only serves as a memorial to his late wife but also explores the unimaginable pain of explaining this loss to his three-year-old daughter. Through raw, unfiltered emotion, Falcon shares the experience of grief while threading a hopeful message about the eternal nature of love.

Recorded in 1991, Pretty Blue World was produced by Jon Bon Jovi and Billy Falcon himself, and it showcases a fusion of rock, folk, and heartfelt balladry. “Heaven’s Highest Hill” stands out on the album for its quiet intensity, with Falcon’s voice carrying both the weight of his personal loss and the hope that love transcends even death. The instrumentation is minimal but effective, giving Falcon’s vocals and the song’s tender lyrics the space they need to fully resonate. The simplicity of the music enhances the emotional impact, allowing listeners to connect with the profound message of the song.

# 8 – How Much I Feel – Ambrosia

“How Much I Feel” by Ambrosia is a classic ballad that masterfully captures the pain of love lost and the lingering emotional weight of infidelity. Released in 1978 on their Life Beyond L.A. album, the song became a massive hit, reaching number three on the Billboard Hot 100. Produced by Freddie Piro, this track was recorded in Los Angeles and features Ambrosia’s signature blend of soft rock and pop with a dash of progressive rock. David Pack’s tender yet powerful lead vocals, paired with the band’s intricate instrumentation, create a hauntingly beautiful piece of music that resonates deeply with anyone who has experienced the complexities of love and regret.

Lyrically, “How Much I Feel” explores the story of a man caught between two loves, reflecting on a relationship he can’t fully let go of, even after moving on. The lyrics “I don’t know how this whole business started, of you thinkin’ that I had been untrue” convey the deep remorse and emotional turmoil of the narrator, who still feels the intensity of his former love. The chorus, “That’s how much I feel, feel for you, baby,” echoes the longing that comes from unresolved feelings. The song’s slow, aching melody enhances the emotional impact, making it one of those rare tracks that pulls the listener into a deeply reflective and sorrowful state. The poignant delivery of Pack’s vocals only intensifies the sense of vulnerability.

Comparatively, within the “10 Sad Songs That Will Always Make You Cry” list, “How Much I Feel” stands out as a song that captures the sadness of personal regret rather than loss through death or tragedy. Its focus on the internal emotional conflict of unresolved love brings a different layer of sadness to the collection. The smooth harmonies and lush production make it an easy listen, but the pain in the lyrics and vocal delivery packs a punch, leaving a lasting impression.

Read More: Top 10 Ambrosia Songs

# 7 – Shannon – Henry Gross

“Shannon” by Henry Gross is a deeply emotional song that tugs at the heartstrings with its poignant narrative of loss. Released in 1976 on his Release album, the song was a tribute to the death of Beach Boys member Carl Wilson’s Irish Setter, Shannon, who had tragically drowned. The track became a hit, reaching number six on the Billboard Hot 100 and resonating with listeners for its universal themes of grief and the pain of losing a beloved companion. Produced by Terry Cashman and Tommy West, the song was recorded in New York City, and it features Henry Gross on lead vocals and guitar, delivering a hauntingly heartfelt performance.

The lyrics of “Shannon” perfectly capture the devastation of losing a cherished pet, with lines like “Shannon is gone, I heard she’s drifting out to sea” embodying the sorrow and longing that follows such a loss. Gross’ tender vocal delivery, paired with the song’s soft rock arrangement, creates an atmosphere of melancholy that makes it hard not to feel the weight of the emotions behind the song. The chorus, with its aching melody, amplifies the sadness as Gross sings about the void left behind by Shannon’s departure. The song’s slow build and gentle instrumentation reflect the inevitability of loss, making it an enduring tearjerker.

In comparison to other songs on the “10 Sad Songs That Will Always Make You Cry” list, “Shannon” stands out for its focus on the loss of a pet rather than a person, yet the emotional impact is just as profound. The song’s simplicity and sincerity in expressing grief make it relatable to anyone who has experienced the pain of losing something precious. Like “How Much I Feel” by Ambrosia, “Shannon” relies heavily on its lyrical poignancy and understated arrangement to convey a deep sense of sorrow, but its unique angle of pet loss gives it a distinct place in the list.

Read More: 1976’s Best Classic Rock Albums

# 6 – Midnight – Yaz

“Midnight” by Yaz is a haunting and emotionally charged track from their debut album Upstairs at Eric’s, released in 1982. The song showcases the duo’s signature synth-pop sound, with Vince Clarke’s minimalist electronic arrangements and Alison Moyet’s soulful vocals. The combination of these elements creates a melancholic atmosphere that is a perfect fit for the song’s deeply introspective and regretful lyrics. The album itself, produced by Yaz alongside E.C. Radcliffe and Mute Records boss Daniel Miller, was recorded at Blackwing Studios in London, and became a key release in the early 80s synth-pop movement. The success of Upstairs at Eric’s, which peaked at number two on the UK Albums Chart and earned platinum certification, was driven by the blend of emotional depth and innovative electronic music that “Midnight” epitomizes.

The song tells the story of a woman wrestling with the pain of losing someone she loves due to her own mistakes. In the lyrics, she reflects on the night it’s “raining outside” and how she let her partner down by cheating while he was working hard to provide. The powerful emotional core of the song comes from her realization that she’s “lost the best thing” she ever had, and now, it’s too late to make amends. Alison Moyet’s raw, soulful voice carries this emotional weight, expressing the inner turmoil of someone full of regret. Lines like “I should have thought of that before I did you wrong” emphasize the finality of her actions, and the heartache that comes from knowing she has no way to undo her mistake. The song’s somber tone is heightened by the rain-soaked imagery, further illustrating the character’s emotional state.

Read More: Top 10 Yazoo Songs

# 5 – Wuthering Heights – Kate Bush

Released as her debut single in January 1978, “Wuthering Heights” catapulted Kate Bush into stardom with its ethereal and haunting composition, instantly making her one of the most unique voices in music. The song is based on Emily Brontë’s famous novel Wuthering Heights and is sung from the perspective of the character Cathy. Bush wrote and produced the song at just 18 years old, inspired by the 1967 BBC adaptation of the novel. It was recorded at AIR Studios in London with assistance from engineer Jon Kelly and produced by Andrew Powell, who also arranged the orchestration. The song features Bush on vocals and piano, with Ian Bairnson on guitar, David Paton on bass, and Stuart Elliott on drums. The track became a number one hit in the UK, staying at the top of the charts for four weeks, and establishing Bush as a groundbreaking artist.

“Wuthering Heights” tells the story of the ghostly character Cathy calling out to her love, Heathcliff, from beyond the grave, longing for reunion. The lyrics, “Heathcliff, it’s me, I’m Cathy, I’ve come home,” capture the tragic, unfulfilled love that defines Brontë’s novel. Bush’s voice, with its high-pitched, almost operatic range, mirrors the spectral nature of Cathy’s ghost. The sorrow in the song is palpable, as Cathy laments their doomed romance and her desire for Heathcliff to come to her. It’s this longing and sense of eternal separation that brings such sadness to the track, making it one of the most emotionally evocative songs in Bush’s discography.

Comparing “Wuthering Heights” to other songs on this list, such as Midnight by Yaz and Heaven’s Highest Hill by Billy Falcon, all explore profound feelings of loss and longing, but where Heaven’s Highest Hill centers on a deeply personal real-life tragedy, and Midnight deals with regret and the yearning for forgiveness, Bush’s song transforms literature’s classic doomed love story into a musical experience. The supernatural, gothic tones in “Wuthering Heights” align it with literary tragedy more than personal heartbreak, but the emotional depth it evokes is just as powerful. As with other songs in this list, the listener is left with an overwhelming sense of grief and yearning, which cements “Wuthering Heights” as a song that will always stir deep emotion and bring tears to the eyes of those who listen.

In terms of critical commentary, “Wuthering Heights” has been praised for its originality and Bush’s willingness to push artistic boundaries. The song is often regarded as one of the greatest debuts in music history, and it marked the beginning of a career defined by experimentation and artistic brilliance. Its influence on pop music, particularly in terms of its narrative storytelling and use of unconventional vocals, cannot be overstated.

Read More: Top 10 Kate Bush Songs

# 4 – Father And Son – Cat Stevens

“Father and Son” is one of the most poignant and timeless songs by Cat Stevens, released on his 1970 album Tea for the Tillerman. The song captures a universal struggle between generations, with a father trying to offer wisdom from his own life experience and a son yearning to break free and follow his own path. The song’s structure and lyrics portray a conversation where Stevens takes on both roles, using a deep, authoritative voice for the father and a higher, more emotional tone for the son. This vocal distinction underscores the emotional distance between the two characters, as they both speak from fundamentally different places of life experience.

Stevens originally penned “Father and Son” as part of a larger musical project, Revolussia, which was set against the backdrop of the Russian Revolution. However, after contracting tuberculosis and nearly dying in 1969, the project was shelved, but the song remained, now more broadly addressing the generational conflicts that define many families. Recording for Tea for the Tillerman took place at Morgan Studios in London, with Stevens playing guitar and providing vocals. Alun Davies, Stevens’ longtime guitarist and collaborator, contributed to the backing vocals, creating a haunting chorus that enhances the song’s emotional intensity. The album was produced by Paul Samwell-Smith, who helped Stevens craft the introspective and delicate sound that became his signature.

Lyrically, “Father and Son” taps into the tension of the older generation trying to instill their values, and the younger generation’s need to carve out their own identity. The father’s advice is filled with well-meaning platitudes: “Find a girl, settle down, if you want you can marry,” but it’s clear the son is driven by a different force, as shown in the heartbreaking lines, “How can I try to explain? When I do, he turns away again.” The son’s realization that he must go on his own journey is bittersweet, making the song one of the most stirring examples of parental misunderstandings. The father’s voice, full of resignation, represents the struggle to accept that his son must make his own decisions, no matter the consequences.

Compared to other songs on this list, such as Shannon by Henry Gross and Wuthering Heights by Kate Bush, Father and Son offers a sadness that is rooted in familial relationships, not the loss of a loved one or the longing for a lost time, but the painful realization that love sometimes means letting go. While Shannon mourns a beloved pet, and Wuthering Heights focuses on the tragic separation between lovers, Father and Son brings listeners to the quieter, but no less profound sadness that comes from a father and child growing apart. The song remains one of the definitive tracks about family dynamics, making it a mainstay in the canon of songs that evoke tears and reflection.

Read More: Top 10 Cat Stevens Songs

# 3 – All Those Years Ago – George Harrison

“All Those Years Ago” is a heartfelt tribute from George Harrison to his late bandmate and close friend John Lennon, released in May 1981 as part of his Somewhere in England album. The song was written in the wake of Lennon’s tragic murder in December 1980, and Harrison tailored its lyrics to reflect his deep grief and admiration for Lennon’s life and legacy. The track features a rare collaboration between three of the former Beatles, with Paul McCartney and Ringo Starr contributing backing vocals and drums, respectively. Notably, it was the first time Harrison, McCartney, and Starr recorded together since the Beatles disbanded, making the song even more significant. It also features contributions from other prominent musicians, such as Al Kooper on keyboards and Ray Cooper on percussion. The track was produced by George Harrison and received positive reviews for its poignant lyrics and nostalgic feel, peaking at number 2 on the US Billboard Hot 100 and number 13 in the UK.

The song reflects Harrison’s emotional journey following Lennon’s death, with the lyrics paying tribute to Lennon’s messages of peace and love, most notably referencing the iconic phrase “All you need is love.” Harrison weaves in reflections on the way Lennon was treated during his life, juxtaposing his friend’s teachings of love and peace with the cruelty and violence he endured. Lines such as “They treated you like a dog” and “You were the one they backed up to the wall” echo Harrison’s frustration with the world that often failed to understand Lennon. The song moves between personal reflections, such as Harrison sending out a prayer to Lennon, to broader themes of spiritual and philosophical musings, characteristic of Harrison’s writing.

Musically, the song combines Harrison’s signature guitar work with elements of the pop-rock sound of the early 1980s. The McCartney-backed harmonies and Starr’s steady drumming add an emotional weight, while the instrumental breaks emphasize the melancholic yet celebratory tone of the track. In comparison to other songs on this list, such as “Father and Son” by Cat Stevens, which explores the complexity of familial relationships, “All Those Years Ago” channels the sadness of losing a close friend, especially one who profoundly impacted global culture. While “Father and Son” addresses generational misunderstandings, “All Those Years Ago” feels like a musical eulogy, steeped in reverence for Lennon’s ideals and legacy.

The lyrical analysis of the song uncovers Harrison’s spiritual reflections, particularly in the lines “Now in the world of light / Where the spirit free of the lies.” This theme of moving from the material world to a spiritual realm echoes Harrison’s long-standing interest in Eastern philosophy and the belief in life after death. Harrison’s direct references to Lennon’s songs, such as “All you need is love” and “Imagine,” remind listeners of the lasting impact Lennon had on the world. The song closes with a final repetition of “All those years ago,” underscoring the passage of time and how Lennon’s influence continues to resonate in the hearts of his friends and fans alike.

Read More: Top 10 George Harrison Songs

# 2 – God Give Me Strength – Elvis Costello and Burt Bacharach

“God Give Me Strength” is an evocative collaboration between Elvis Costello and Burt Bacharach, originally composed for the 1996 film Grace of My Heart. The song stands as a centerpiece in their 1998 album Painted from Memory, a project that united the talents of both Costello and Bacharach after decades of notable individual success. This deeply emotional track, with its sweeping orchestral arrangements and Costello’s raw, heart-wrenching vocals, captures the despair of loss and the yearning for strength in the face of heartache. It was recorded at Ocean Way Recording in Hollywood, with production by Costello, Bacharach, and Kevin Killen. The resulting song is one of the most powerful moments on the album, fusing Bacharach’s classic approach to melody and harmony with Costello’s unparalleled lyrical intensity.

The lyrics of “God Give Me Strength” paint a vivid portrait of someone at their emotional breaking point, pleading for divine assistance to endure the pain of losing a love that was once cherished. Lines like “She took my last chance of happiness” and “Now I have nothing” capture the depth of this grief, while the singer’s plea for strength underscores the feeling of being powerless. The song transitions between quiet introspection and moments of dramatic vocal crescendo, mirroring the internal emotional struggle. Costello’s vocal performance carries the weight of the sorrow, supported by Bacharach’s lush yet restrained musical arrangement. The collaboration perfectly blends Costello’s poignant storytelling and Bacharach’s mastery of orchestral pop.

Critically, the song and the album as a whole were well received, praised for its elegant arrangements and emotional resonance. God Give Me Strength was highlighted as one of the standout tracks, setting the tone for the rest of Painted from Memory. Like other songs on this list of “Sad Songs That Will Always Make You Cry,” it taps into the universal experience of loss and longing. The song’s climactic moments—particularly the desperate refrain of “So God give me strength”—are reminiscent of other heart-wrenching songs like Father and Son by Cat Stevens, where the depth of emotional conflict drives the listener to feel the intensity of the song’s message.

“God Give Me Strength” delves into themes of vulnerability and human fragility, making it a perfect fit for this collection of deeply emotional songs. Its orchestration, combined with Costello’s lyrical mastery, ensures that it resonates as a timeless anthem of sorrow and resilience.

Read More: 25 Essential Elvis Costello Songs And Fan Favorites

Read More: Top 20 Burt Bacharach Songs Loved By Fans

# 1 – Leader Of The Band – Dan Fogelberg

This is the closing song on our list. It’s also one that always makes me cry whenever I hear it. Anyone who’s ever experienced the loss of their father understands exactly what I’m talking about. “Leader of the Band,” written by Dan Fogelberg and released in 1981 on his album The Innocent Age, is a deeply emotional tribute to his father, Lawrence Fogelberg, a talented musician and bandleader. The song was released while Fogelberg’s father was still alive, but after his death in 1982, it became even more poignant. The song not only celebrates the life of his father but also touches on the bittersweet reality of losing a parent, and it remains one of Fogelberg’s most beloved tracks. The single reached number nine on the Billboard Hot 100 and topped the Adult Contemporary chart, solidifying its place as a timeless song about family and legacy.

For anyone who has lost a father, “Leader of the Band” is a song that always stirs deep emotions. There is something about Fogelberg’s tender delivery and the way he captures both the pride and sorrow of reflecting on a father’s life that brings tears to the listener’s eyes. This song is not just a celebration of a father’s role but an acknowledgment of how difficult it is to lose them, even when remembering the good times. As you listen, Fogelberg’s voice seems to comfort, encouraging you to appreciate the love you shared, but it’s still hard to hear without feeling the weight of loss.

The lyrics bring this feeling home: “The leader of the band is tired, and his eyes are growing old, but his blood runs through my instrument, and his song is in my soul.” These lines speak to the deep connection between father and son, and how the father’s influence continues to live on through his child. Fogelberg conveys a sense of gratitude with lines like, “I thank you for the music and your stories of the road,” reminding us of the gifts we often take for granted until it’s too late. The song is both a tribute to a life well-lived and an expression of the painful reality of saying goodbye.

The closing line, “I am a living legacy to the leader of the band,” is a profound statement of how our loved ones live on through us, even after they are gone. As the final song on this list of sad songs that will always make you cry, “Leader of the Band” resonates deeply because it so perfectly captures the blend of heartache and appreciation for a father’s love. It’s a reminder to cherish those moments, even if they bring tears.

Read More: Top 10 Dan Fogelberg Songs