30 Songs That Became Heartbreaking After the Truth Came Out

Welcome to WatchMojo, and today we’re looking at some iconic tracks that are heartbreaking in hindsight.

“Heavy” (2017)

Linkin Park feat. Kiiara

When this song came out, it was met with quite a bit of criticism. Its radio-friendly, somber tone was a far cry from the gritty, unrestrained nu-metal the band was known for. Critics likened this change in sound to a bid for commercial success. However, fans saw the pain behind the lyrics. In several interviews at the time, frontman Chester Bennington opened up about the song being inspired by his own mental health struggles. In fact, the harrowing words that open the song were a direct reflection of his mental state. After living with depression for years, Bennington took his own life a few short months after the song was released, changing the way people heard “Heavy” forever - and it’s not the only Linkin Park track on this list.

“Waiting Around to Die” (2017)

Power Trip

For years, this powerful song has brought strength to people who might be in a dark place in their lives. The lyrics urge the listener to take charge of their life instead of letting it pass them by. However, this uplifting message took on a haunting poignancy when the man singing it, Power Trip’s vocalist Riley Gale, passed away at the age of thirty-four. His untimely death was reportedly linked to an accidental overdose. Despite dealing with depression himself, Gale was dedicated to making the world a better place. To this day, “Waiting Around to Die” remains a potent song of hope.

“Rock the Boat” (2001)

Aaliyah

The Princess of R&B released this song at a time when her career was skyrocketing. Aaliyah was not only an immensely successful singer, but was also making a name for herself as an actress in Hollywood. “Rock the Boat” was a major hit, peaking at number two on Billboard’s U.S. Hot R&B/Hip-Hop Songs chart and the U.S. R&B Digital Song Sales chart. It even bagged her a Grammy nod! All that was left was a music video. Unfortunately, the day Aaliyah wrapped up filming for the MV, she got into a tragic plane crash that claimed nine lives, including her own. Although the video was released a few weeks after her passing, no one could watch it without grieving.

“Save the Last Dance for Me” (1960)

The Drifters

Decades have passed since the world was blessed with this song, and the sheer romance of it hasn’t diminished one bit. Ben E. King sings of a lovely lady who’s the life of the party. She’s dancing the night away, but the narrator wants her to know that her heart belongs with him. It was later revealed that Rock and Roll Hall of Famer Doc Pomus wrote this song about his wife on the day of their wedding. His collaborator, Lou Reed, shared the story on Elvis Costello's “Spectacle”. Pomus lived with polio, which left him unable to dance with his newlywed bride, Broadway actress Willi Burke, who was also a dancer. This gave the song a bittersweet dimension, but we love it nonetheless.

“Everytime” (2003)

Britney Spears

Considering everything the Princess of Pop has been through, fans can’t help but find echoes of her pain in her discography. In the early aughts, when her split from Justin Timberlake became tabloid fodder, she wrote “Everytime” alongside Annet Artani, who was also going through a painful breakup. Artani was a background singer for Spears during her Dream Within a Dream Tour, and told Insider that the songwriting process was “cathartic”, involving a lot of tears. After Spears revealed in her memoir “The Woman in Me” that she was once pregnant with JT’s child and he had allegedly asked her to terminate the pregnancy, fans speculated that “Everytime” may have references to that experience as well. That connection is unconfirmed, but the thought still hurts.

“Badfish” (1991)

Sublime

On May 25, 1996, at the young age of twenty-eight, Bradley Nowell left this world. He was on tour with Sublime back then and had reportedly abstained from substance use for a while, until he relapsed and passed away from an overdose of heroin. This makes the band’s 1991 song “Badfish” even more heartbreaking. The lyrics, written by Nowell, are supposedly about someone who’s struggling with substance use, but tries to drag others down the same path. It’s said that the Sublime frontman hadn’t tried heroin before the song was released. His father later claimed that his desire to be “larger than life” pushed him to try it, which led to his substance use disorder. Nowell’s music lives on, but he is dearly missed.

“Keep Me in Your Heart” (2003)

Warren Zevon

It is virtually impossible to listen to this song without breaking into tears. The lyrics are from the perspective of someone who knows their time in the world is coming to an end. They’re comforting their loved ones, hoping they hold on to their memory for at least a little while. Days after the song was released, Warren Zevon passed away. He had been living with a type of cancer called mesothelioma for some time and had reportedly written “Keep Me in Your Heart” after finding out his illness was terminal. Fans have theorized that the song may be dedicated to Zevon’s then-girlfriend or his ex-wife, Crystal, or both, and possibly other family members he left behind.

“God” (1970)

John Lennon

The Beatles member wrote this song as an ode to personal sovereignty. He rejected the influence of religion and false idols like Elvis and The Beatles on his worldview, instead relying on himself and his beloved, Yoko Ono. Almost a decade after the song was released, John Lennon was fatally shot by Mark David Chapman. According to reports, the murderer was apparently outraged by the Grammy-winning singer’s lyrics to “Imagine”. Lennon’s comment about The Beatles being “more popular than Jesus”, which was considered blasphemous by the Christian right, reportedly intensified Chapman’s hostility toward him. However, it seemed the song “God” was particularly infuriating to him because of Lennon’s lack of belief in Jesus. It’s devastating to think that this anger led to the legend’s death.

“Hurt” (2002)

Johnny Cash

The country music star’s rendition of the Nine Inch Nails song is widely considered one of the highlights of his illustrious career. The music video, set in the House of Cash museum and directed by Mark Romanek, earned him a Grammy, too. The song explores themes like mortality and legacy, which are portrayed in the music video through a juxtaposition of Cash’s glory days with the quiet dignity of age. At the time, Cash was living with autonomic neuropathy, a complication related to his diabetes, but his music still captivated fans worldwide. Unfortunately, he broke down emotionally when his wife, June Carter, died some time after the cover was released, and a few months later, Johnny left us, too.

“Hail Mary” (1996)

Makaveli feat. Outlawz

New York City rap legend Tupac Shakur recorded this song in July of 1996. The lyrics are charged with Biblical allusions on the one hand, and violent imagery on the other. The verses conjure a dark world where enemies are struck down, and death is hardly feared, even if hell awaits, but the rapper is also seeking redemption. Tragically, on September 13, 1996, Shakur passed away, a few days after being shot. “Hail Mary” was released posthumously under his stage name Makaveli as a part of “The Don Killuminati: The 7 Day Theory” album, taking on a chilling new weight.

“Juicy” (1994)

The Notorious B.I.G.

A classic tale of going from rags to riches, "Juicy" is a song of triumph. However, the Notorious B.I.G.’s celebration of his rise to the top after a lifetime of struggle is forever altered by what happened just under three years later. On March 9, 1997, the rapper, born Christopher Wallace, was shot four times while a passenger in a car. He was pronounced dead shortly after, at age 24. In the time since his murder, Biggie has been rightfully regarded as one of the greatest rappers in history. And “Juicy” is arguably his signature song. But its joy is greatly impacted by what would eventually happen.

“A Fond Farewell” (2004)

Elliott Smith

Released posthumously after the singer-songwriter’s tragic death at age 34, Elliott Smith’s final album, “From a Basement on the Hill,” is devastating. Like much of Smith’s catalog, it addresses substance use disorder and mental health troubles in ways as poetic as they are painful. On this standout track, Smith reckons with the cost of trying to numb himself through life. But in the chorus, he stresses that his life is not actually his. And titling it “A Fond Farewell" makes it especially gut-wrenching. While he left our world more than 20 years ago, his craft and unapologetic honesty has kept him in our hearts.

“Goodbye to Love” (1972)

Carpenters

During their time, the Carpenters were dismissed by elitists as making music that was overly sentimental and insubstantial. But while siblings Karen and Richard Carpenter were promoted with a wholesome, uncomplicated public image, what was happening behind the scenes was far more serious. Karen's issues with her body and eating became clear by the mid-70s, with her gaunt appearance causing concern. More than a decade before she passed, the band recorded “Goodbye to Love.” While Karen didn’t write the lyrics, her singular voice carries every word. Perhaps the most haunting moment of this song comes early when she laments about no one caring whether or not she lives. Though the song might not be directly about her struggles, it doesn’t make it any less poignant.

“Dreaming of You” (1995)

Selena

"The Queen of Tejano Music," Selena Quintanilla-Pérez's legacy has not diminished. Just two years short of her tragic death, a biopic about the artist, starring Jennifer Lopez and made with the cooperation of her family, was released. In the film's closing moments, we hear her moving ballad "Dreaming of You". This is interrupted by news of her murder at the hands of Yolanda Saldívar, president of her fan club. The song continues playing over mourning and images of the real-life singer. It’s a conclusion all but guaranteed to make you weep, one that made this track forever an emotional one.

“Perfect Circle / God Speed” (2015)

Mac Miller

Mac Miller’s struggles with substance use disorder wasn’t a topic he shied away from addressing in his music. In this nearly 8-minute two-parter from his 2015 album, “GO:OD AM,” Miller talks about concerns over his well-being, including the possibility of his death via overdose. Sadly, that’s what happened less than three years later. Beyond the foreboding lyrics, “Perfect Circle / God Speed” is also a remarkable showcase of Miller’s talents as an artist and performer. But knowing what was to come, it’s difficult to appreciate it as a piece of music and not a cry for help.

“Rehab” (2006)

Amy Winehouse

Another song about an artist’s struggle to fend off their demons, it was all but impossible to avoid “Rehab” after it dropped. And the more it was played, the more apparent it was that Amy Winehouse had gone through a lot. A soulful and endlessly catchy song about her refusal to get treatment, “Rehab” is a testament to Winehouse’s powerhouse presence. That she could tackle such a complicated subject with such conviction is exactly why she became a global sensation. And the song took home three Grammys, including Record of the Year and Song of the Year. Though Winehouse did eventually check into a rehab facility in 2008, her challenges persisted. She passed away from alcohol poisoning in 2011, at age 27.

“Jeepster” (1971)

T. Rex

The second single released from T. Rex's second album, "Jeepster" captures the glam rock legends in top-notch form. It’s a hooky song in which frontman Marc Bolan likens himself and the object of his affection to vehicles. If you aren’t familiar with Bolan’s story, it might seem like a silly novelty and not much more. Despite the song’s carefree vibe, Bolan feared dying in a car accident, and never tried for his license as a result. In 1977, Bolan was a passenger in a car driven by his romantic partner, singer Gloria Jones. She hit a fence post before colliding into a tree, resulting in Bolan’s death at age 29.

“Floating in the Forth” (2008)

Frightened Rabbit

As the frontman and primary songwriter of the Scottish indie rock band Frightened Rabbit, Scott Hutchison crafted lyrics so personal and evocative that listening feels like reading someone’s very private diary. In this intense song from the band’s second album, Hutchison talks about contemplating taking his own life, with the title referring to Scotland’s River Forth. Tragically, in 2018, Hutchison disappeared and his body was found on the banks of the Firth of Forth, an estuary that the River Forth flowed into. His family later confirmed he had taken his own life, and this song in particular took on even heavier significance.

“Wake Me Up” (2013)

Avicii

The lyrics and vocals from this global EDM smash come from singer Aloe Blacc, who’s uncredited. But even if Swedish DJ Avicii’s voice isn’t heard during “Wake Me Up,” his 2018 death added a new layer of depth to this propulsive song. Blacc sings pleadingly to be woken up on an unspecified future date when he’s older and better able to handle life’s challenges. Avicii grappled with mental health struggles, and he ended up taking his own life at 28. While listening to “Wake Me Up” now may bring back memories of Summer 2013, it’s also a painful reminder of an incredible talent gone too soon.

“Whatever” (2002)

“Our Lady Peace

There's no apparent tragedy associated with this song and the members of Canadian alt-rock outfit, Our Lady Peace. But it has still taken on some very disturbing connotations. A non-album song, “Whatever” was the entrance song of WWE wrestler Chris Benoit. In 2007, Benoit killed his wife and son before taking his own life, in one of the darkest sagas in the history of pro wrestling. Our Lady Peace hadn't regularly performed the song in the years leading up to this tragedy and even claimed they'd never again perform it. Though they did bring it back into rotation for their 2025 tour, we can’t blame anyone for not being able to handle listening to this song.

“Blackstar” (2015)

David Bowie

The Starman himself shocked the world by announcing “Blackstar,” his first studio album since 2013’s “The Next Day,” but in typical Bowie fashion, the biggest twist was yet to come. “Blackstar,” the album, was released on January 8, 2016… and Bowie died on January 10, merely two days later. Having kept his battle with liver cancer a secret known only to those closest to him, “Blackstar’s” title song hits differently now that we know the circumstances of the singer’s death. Pay particular attention to its cryptic, morbid lyrics, which seemingly allude to Bowie finding peace and tranquility in his final days. This calls to mind Leonard Cohen’s “You Want It Darker,” also recorded shortly before the beloved Canadian singer-songwriter’s 2016 death.

“Scared of the Dark” (2018)

Ty Dolla $ign & Lil Wayne feat. XXXTentacion

Commissioned for the soundtrack to Sony Pictures’ Oscar-winning “Spider-Man: Into the Spider-Verse,” Grammy winner Dwayne “Lil Wayne” Carter teased a special guest on “Scared of the Dark,” his collaboration with Ty Dolla $ign. That guest, upon the film’s release, was revealed to be late rapper XXXTentacion. Born Jahseh Onfroy, the controversial artist lost his life in 2018 after a botched robbery attempt. Originally intended for the Bhad Bhabie song “Trust Me,” Onfroy’s verse combines typical hip hop bravado with the dark vulnerability he was known for in his lifetime. This verse, combined with the song’s empowering chorus, now makes for difficult listening.

“I’m Not Gonna Miss You” (2014)

Glen Campbell & The Wrecking Crew

Legendary country singer Campbell, who was open about his worsening Alzheimer’s disease in his final years, made it clear that he wouldn’t die without a fight ahead of his 2017 passing. “I’m Not Gonna Miss You” is emblematic of the icon’s refusal to give in, recorded for and appearing prominently in the 2014 documentary “Glen Campbell: I'll Be Me”. Nominated for the Academy Award for Best Original Song, and winning the Grammy for Best Country Song, this cinematic, John Lennon-esque ballad finds Campbell coming to terms with his impending death. The last song Campbell ever recorded, “I’m Not Gonna Miss You” is a simple, gorgeous, and heartbreaking send-off to a long and storied career.

“Grace” (1994)

Jeff Buckley

Some of the greatest artists of all time, like Vincent Van Gogh or Buckley’s fellow troubadour Nick Drake, went underappreciated in their lifetimes. It seems fair to say that Buckley falls into this category of artists as well. Buckley once referred to the titular song from his 1994 album “Grace”, the only album he released during his life, as being “about not feeling so bad about your own mortality when you have true love.” The multi-talented musician’s plainly-spoken acceptance of his mortality and his seeming lack of fear or apprehension about exiting this mortal coil read very differently after his 1997 drowning, aged only 30, leaving mourning listeners to wonder what could have been.

“Nutshell” (1994)

Alice in Chains

When asked which song most reminded him of late Alice in Chains frontman Layne Staley, the band’s bassist, Mike Starr, responded with “Nutshell,” citing its poetic, vulnerable lyrics as the reason. Listening to the song, it becomes obvious as to why Starr, who passed away himself in 2011, made this particular selection. This mellow grunge tune, written by Staley, details the singer’s battle with his darkest feelings; Staley later died in 2002 following years of extreme substance use issues. It’s no surprise, then, that Jerry Cantrell, the band’s guitarist and alternate lead singer, now dedicates live performances of “Nutshell” to both of his fallen bandmates.

“Free Bird” (1973)

Lynyrd Skynyrd

It must be remembered that this nearly-ten-minute Southern rock epic, despite its hard-charging sound and legendary guitar solos, is, at its heart, a heart-wrenching ballad about being unable to conform to life and its expectations. Written by Allen Collins and Ronnie Van Zant, the band’s guitarist and lead singer, respectively, “Free Bird’s” lyrics tell the first-person story of a nomad who simply can’t overcome his unchanging nature — though certainly not without regrets and reservations. While “Free Bird” is sad enough on its own, already dedicated by the band to the late Duane Allman, it became a retroactive tribute to Lynyrd Skynyrd band members (including singer Van Zant) who died in the 1977 plane crash that temporarily ended the band.

“Like a Stone” (2003)

Audioslave

Chris Cornell, Audioslave’s lead singer, was, and still is, widely regarded by fans and critics alike as one of rock music’s greatest, most iconic voices. Despite this, Cornell was reportedly haunted by struggles with depression, drugs, and drink for the majority of his life, dating back to as early as his teen years. These struggles came to an end in May 2017, when the Soundgarden frontman was found lifeless following a concert in Detroit. While fans will point out that Cornell was no stranger to incorporating dark, highly personal themes into his music, “Like a Stone” stands out in his discography in terms of how plainly it expresses those themes.

“Morphine” (1997)

Michael Jackson

One of the King of Pop’s darkest, rawest, and heaviest tunes, the Nine Inch Nails-esque “Morphine” finds Jackson incorporating heavy guitars and distorted drums into his sound. Fittingly enough, too — “Morphine” is a bitter, angry, no-holds-barred account of Jackson’s feelings regarding his fame and media speculation about his controversial personal life. The song’s bridge and refrain detail Jackson’s resorting to drug use as a means of numbing those feelings. The singer died in 2009 of “acute propofol intoxication” in what was later ruled an accidental homicide by Conrad Murray, Jackson’s personal doctor. Listening in retrospect allows listeners a tragically prescient glimpse into Jackson’s fragile mental state.

“The Show Must Go On”

Queen

It goes without saying that Freddie Mercury was a rock star until the very end. Released just over a month before Mercury’s untimely death from complications of HIV/AIDS, “The Show Must Go On,” in the band’s characteristically bombastic style, is a gloriously defiant “screw you” to the Grim Reaper. Written by Queen guitarist Brian May, the song does a magnificent job of capturing Mercury’s indomitable spirit and interstellar charisma. His body ravaged by the disease even then, Mercury’s bandmates were initially pessimistic that he would be able to pull off the vocal gymnastics it called for. In response, the rock god downed a shot of vodka and, according to May, immediately nailed it. Who else but Freddie?

“Leave Out All the Rest” (2007)

Linkin Park

A staple of the early 2000s “nu metal” scene, it can be argued that Linkin Park’s success outside of that genre was due in large part to lead singer Chester Bennington’s soul-baring, unflinching songwriting, as well as his powerhouse vocals. Phoenix, Arizona native Bennington took his own life in July 2017, two months after Chris Cornell’s death — the two were reportedly close friends. Knowing that makes it difficult, then, to listen to “Leave Out All the Rest,” from the band’s 2007 album “Minutes to Midnight,” without a teary eye by the end. A plaintive, heartfelt rock ballad, “Leave Out All the Rest” implores listeners to, as hard as it can feel, remember the good times.

Can you listen to these songs without crying? Tell us in the comments down below!