65 Best Breakup Songs of All Time

Sometimes, breakup songs can heal you. Knowing that what one is feeling is valid and not new can be healing, even if the sentiments are painful and uncomfortable. Or one can just admire the artistic aspect of converting difficult emotions into music. Here is a list of the 64 best breakup songs of all time.

I Heard It Through the Grapevine by Marvin Gaye

Only a year after Gladys Knight and the Pips took it to the top of the R&B chart, Marvin Gaye made “I Heard It Through The Grapevine” his signature hit. Despite its initial rejection, the song became a classic.

Gaye’s intense version, released on October 30, 1968, quickly rose to No.1 on the Hot 100 and became Motown’s biggest-selling single. The song also hit No.1 in the UK in March 1969 and was later voted the UK’s favorite Motown song in 2014. Numerous artists, including Creedence Clearwater Revival and Roger, have since covered the timeless track.

It’s Over by Roy Orbison

Roy Orbison discussed “It’s Over” with NME in 1980, explaining that the song’s lyrics reflect a realization that something has ended before one becomes aware of it.

The song reached #1 in the UK on June 25, 1964, making Orbison the first American to top the charts since Elvis in 1962. Bill Dees, who co-wrote 64 songs with Orbison, contributed to “It’s Over.”

The song, structurally similar to “Running Scared,” builds from a whisper to a scream with a bolero-like beat. Many artists, including Glen Campbell, Morrissey, and Bonnie Tyler, have covered it. Producer Fred Foster praised Orbison’s ability to express deep emotions in his music.

Goodbye to Love by The Carpenters

“Goodbye to Love” by the Carpenters, released in 1972, is considered the original power ballad and inspired countless similar songs in the 1980s. Written by Richard Carpenter and John Bettis, the song was influenced by a 1940 Bing Crosby film, “Rhythm on the River.” The song’s signature fuzz guitar solo, played by Tony Peluso, added a unique edge and was praised by DJ John Peel.

Despite initial resistance from some fans and Adult Contemporary radio stations, the song reached No. 7 on the Billboard Hot 100 and became the first Carpenter/Bettis composition to break into the US Top 10.

I Will Survive by Gloria Gaynor

Few tracks in pop history are as legendary as Gloria Gaynor’s 1978 disco hit, “I Will Survive.” Renowned for its memorable hooks and empowering lyrics, it has become the quintessential break-up anthem. The song’s backstory is as intriguing as its enduring popularity. With the release of a new documentary about Gaynor’s life, “Gloria Gaynor: I Will Survive,” we gain fresh insights into this classic tune.

Originally intended as the B-side to “Substitute,” “I Will Survive” was written by Freddie Perren and Dino Fekaris. Gaynor immediately recognized its timeless quality and pushed for its promotion to the A-side, despite initial resistance from her record label. Her determination paid off as the song topped charts in both the US and UK in 1979.

The track’s infectious disco rhythm and uplifting message resonated with a wide audience, making it a favorite on dance floors. With a tempo of 117 beats per minute, it remains perfect for dancing and cardio exercise. The song’s influence spans generations, with covers by artists like Harry Styles and Madonna. “I Will Survive” continues to be a symbol of strength and resilience, celebrated for its universal appeal and timeless message.

Since U Been Gone by Kelly Clarkson

Although the song was a hit, Clarkson had quite a few grievances with it.

Kelly Clarkson revealed on ‘Watch What Happens Live’ that she was misled about the creation of her hit “Since U Been Gone.” She was told she’d collaborate on the lyrics with Max Martin and Dr. Luke but found they had already written them. Feeling misled, she said this caused a “bad vibe” with the song. Despite this, she still performs it passionately. Clarkson has had disputes with Clive Davis over his 2013 memoir, which she says contains inaccurate stories about her reluctance to release the song. Davis stands by his account.

Nonetheless, Kelly’s powerful voice and the song’s message still make it one of the best breakup songs of all time.

The Winner Takes It All by ABBA

‘The Winner Takes It All’ is one of ABBA’s most poignant breakup songs. Written by Benny Andersson and Björn Ulvaeus, it was originally titled ‘The Story of My Life’ and sung by Agnetha Fältskog, coinciding with her divorce from Ulvaeus.

Though Ulvaeus denies the song is directly about their divorce, he acknowledges it’s about the emotions of divorce in general. The song placed Agnetha in the unique position of singing a breakup song written by her ex-husband shortly after their split.

The music video was filmed in Marstrand, Sweden, and the song topped UK charts in 1980. Meryl Streep covered it in the ‘Mamma Mia!’ film, earning high praise from Björn.

I’d Rather Go Blind by Etta James

The B-side of “Tell Mama,” titled “I’d Rather Go Blind,” elevates the single to legendary status, akin to the Beatles’ “Strawberry Fields”/”Penny Lane.” Its soul-blue rhythm and melody provide a gentle yet authoritative guide. Lyrically confessional, it reaches the emotional depth of great gospel songs of the 20th century.

The premise of the title alone is poignant, but the poetic lyrics elevate it further. Etta James’ unmatched vocal delivery drips with emotion, infusing the song with an undeniable bittersweet feeling. Overall, it stands as a masterpiece, blending heartbreak and soulfulness into a recording of exceptional artistic merit.

Ms Jackson by OutKast

OutKast’s second single, “Ms. Jackson,” from the album Stankonia, launched them into the mainstream by reaching the top 5 in many countries and becoming their first of three Billboard Hot 100 #1 hits. It also earned them the Grammy for Best Rap Performance by a Duo or Group in 2002. They chose the name “Jackson” because it’s widely recognizable.

André and Big Boi drew on personal experiences to create the song, with André specifically reflecting on his relationship with Erykah Badu, which influenced his verse. André explained that the song stemmed from pondering the feelings of a parent in a complex family dynamic after a relationship ends badly. Thus, it is an unconventional breakup song in which the singer addresses his ex-lover’s mother and apologizes to her for the breakup.

While “Ms. Jackson” was a sensitive subject for Badu, she shared in 2016 that her mother embraced being the song’s inspiration, even getting a license plate that reads “MSJACKSON.”

Make Me Smile (Come Up and See Me) by Steve Harley and Cockney Rebel

Steve Harley, singer-songwriter of Cockney Rebel, reflects on the creation of “Make Me Smile (Come Up and See Me)” and its deeper meaning. In 1974, amidst their rising fame with hits like “Judy Teen” and “Mr Soft,” Harley’s band faced internal turmoil when three members wanted to contribute to songwriting, leading to their departure. Along with loyal drummer Stuart Elliott, Harley continued under the name Steve Harley and Cockney Rebel.

The song “Make Me Smile” emerged from this period, with Harley subtly referencing the departed members in its lyrics. Producer Alan Parsons suggested accelerating the song’s tempo, which masked its bitter undertones. Upon its release, the track soared to No. 1, marking a poignant moment amidst personal and professional challenges for Harley and the band. Thus, the band’s breakup was authentically translated into a sad song.

You’re So Vain by Carly Simon

“You’re So Vain,” released in 1972, remains Carly Simon’s most iconic and enduring song. Known for its catchy melody and enigmatic lyrics, the song reached number one on the Billboard Hot 100 chart and became a global sensation.

The song’s lyrics describe a self-absorbed lover who is so conceited that he doesn’t realize the damage he causes. One of the most intriguing aspects of the song is its subject, which Simon kept secret for many years. Speculation swirled around various celebrities, including Mick Jagger, Warren Beatty, and others, adding to the song’s mystique.

In 2015, Carly Simon finally revealed that the second verse of “You’re So Vain” refers to Warren Beatty, though the entirety of the song’s subject remains a composite of several men in her life. This revelation sparked renewed interest in the song and solidified its place in pop culture history.

“You’re So Vain” continues to be a beloved classic, renowned for its lush production, Simon’s soulful vocals, and its timeless portrayal of vanity and self-absorption. Its enduring popularity underscores Carly Simon’s talent as a songwriter and performer whose music resonates across generations.

If You See Her, Say Hello by Bob Dylan

Bob Dylan’s “If You See Her, Say Hello” from “Blood on the Tracks” explores heartache and longing. Released in 1975, the song reflects Dylan’s masterful storytelling and emotional depth, capturing the aftermath of a fractured relationship. Although Dylan has suggested the album’s songs aren’t strictly autobiographical, the raw emotion and intimate lyrics resonate deeply.

The track’s sparse arrangement and Dylan’s soulful delivery highlight its melancholic theme, making it a standout on an album revered for its storytelling prowess and musical richness. “Blood on the Tracks” remains a testament to Dylan’s enduring influence and songwriting brilliance.

When You Were Mine by Prince

“When You Were Mine” is the second track on Prince’s album “Dirty Mind,” released in 1980. It was briefly available as a promotional single later that year alongside “Head.”

In 1993, it appeared on Prince’s compilation album “The Hits 1,” and in 2002, a live version titled “When U Were Mine” was included on his live album “One Nite Alone… Live!”

The album was recorded between May and June 1980 at Prince’s North Arm Drive Home Studio in Orono, Minnesota, referred to as “Somewhere in Uptown,” and completed at Hollywood Sound Recorders in Los Angeles, California. It highlights Prince’s versatile musical talents and evolving style.

Say Hello, Wave Goodbye by Soft Cell

“Say Hello, Wave Goodbye” by Soft Cell is another iconic track that resonates deeply with its listeners.

Known for its poignant lyrics and emotional delivery, this song captures themes of farewell and longing, making it a poignant anthem of its time.
Marc Almond’s vocals, coupled with the band’s distinctive sound, create a melancholic atmosphere that resonates long after the song ends. Together with “Tainted Love,” these tracks define Soft Cell’s legacy of blending pop with deep emotional undertones, offering listeners a journey through nostalgia and raw sentimentality that remains compelling decades later.

Walk Away Renée by The Left Banke

“Walk Away Renee,” written by Michael Brown and released in 1966, has a lingering mystery about its inspiration. While often attributed to Left Banke bassist Tom Finn’s girlfriend, Renee Fladen-Kamm, co-writer Tony Sansone has consistently refuted this claim. Despite the ambiguity, the song became a notable hit for its poignant lyrics and melody.

The Four Tops’ cover in 1967 also achieved success, reaching #14 on the Billboard Hot 100 chart, further cementing the song’s enduring appeal across different interpretations and renditions.

“Walk Away Renee” by The Left Banke, penned by 16-year-old Michael Brown, resonates deeply despite its youthful origins. The song, which reached #5 on the pop charts in 1966, is a poignant exploration of unrequited love. Brown wrote it about Renee Fladen, the girlfriend of bandmate Tom Finn, who was present during the recording sessions.

The baroque pop sound, enhanced by Brown’s harpsichord and string arrangements, evokes a melancholic nostalgia. The lyrics, narrated by a man haunted by memories of Renee, reflect on lost love and the painful realization of letting go. Despite their brief tenure, “Walk Away Renee” secured The Left Banke’s place in music history.

Cold Cold Heart by Hank Williams

“Cold, Cold Heart,” one of Hank Williams’ most enduring songs, catapulted him to new heights of fame and influence upon its release in early 1951.
Initially recorded as a B-side, the plaintive ballad quickly overshadowed its A-side counterpart on both country and pop charts.

Inspired by personal turmoil with his wife Audrey, the song’s melancholic lyrics and Williams’ emotive delivery resonated widely. Tony Bennett’s orchestral cover further solidified its crossover appeal, marking it as a timeless classic in the American songbook.

Despite Williams’ initial reservations about pop interpretations, “Cold, Cold Heart” remains a beloved standard covered by artists across genres.

The Rain by Oran ‘Juice’ Jones

Oran “Juice” Jones is known for his unapologetically direct approach in his R&B ballad, where he confronts his lady after seeing her with another man. He swiftly packs her bags and delivers a memorable breakup monologue, questioning her motives and highlighting what he provided her. Jones’ delivery is both cutting and humorous, culminating in a memorable line: “You without me is like cornflake without the milk!” His song showcases his vocal prowess and his knack for delivering sharp, memorable lines that resonate with listeners.

Ex Girl to Next Girl by Gang Starr

It sounds like Guru enters a reflective mode in his storytelling, sharing experiences about his relationships with women. His approach seems to involve moving on quickly from one ex-girlfriend to the next, leaving behind any issues they had.

The track’s introduction and hook parts creatively incorporate a sample from “Funk It Up” by Caesar Frazier, adding a funky and rhythmic element to Guru’s narrative. This blend of storytelling and musical sampling likely enhances his music’s overall vibe and theme, reflecting his style and approach to relationships. Moreover, it’s a song that focuses on following breakups with bad coping mechanisms.

Torn by Natalie Imbruglia

The music video for “Torn” by Natalie Imbruglia, from her album “Left of the Middle” on RCA Records, depicts a locked-off shot of an apartment room where Natalie Imbruglia sings alongside her boyfriend. Throughout the video, the director and set crew frequently interrupt the scene to adjust the positioning of Imbruglia and her boyfriend, creating a sense of controlled chaos and behind-the-scenes glimpses into the making of a music video.

This approach adds a meta layer to the video, blurring the lines between reality and performance while showcasing the process of creating visual content for the song. Subsequently, it unravels how disruptions in a relationship can finally cause one to break up.

Un-Break by Heart by Toni Braxton

Toni Braxton’s career soared with hits like “Un-Break My Heart,” a heart-wrenching ballad about lost love from her 1996 album. The song topped the charts globally and became her signature. Amidst personal struggles, including financial woes and health battles with lupus, Toni continued to captivate audiences. Her openness about lupus and family dynamics, showcased in “Braxton Family Values,” endeared her to fans.

Despite announcing retirement, her Grammy-winning reunion with Babyface affirmed her enduring influence in R&B. Toni’s journey, from chart-topping success to personal adversity, resonates through her music’s emotional depth, cementing her as an icon of resilience in the music industry.

Go Your Own Way by Fleetwood Mac

“Go Your Own Way” by Fleetwood Mac is a poignant breakup anthem that showcases Lindsey Buckingham’s emotional turmoil. It starts with raw honesty as Buckingham confronts the realization that love isn’t enough, reflected in lines like “Loving you / Isn’t the right thing to do.” His offer of devotion is met with rejection, emphasizing the painful disconnect in their relationship.

The chorus, “You can go your own way,” resonates as a liberating yet sorrowful plea for separation. The song’s repetition underscores the inevitability of parting, culminating in a resigned acknowledgment of loneliness. It’s a powerful portrayal of love’s complexities and the agony of letting go.

End of the Rod by Boys II Men

“End of the Road” by Boyz II Men is a soulful ballad that captures the heartache of a relationship nearing its end. The lyrics express the anguish of one partner who senses the impending breakup but is unwilling to let go. Released in 1992, it became Boyz II Men’s first number-one single on the Billboard Hot 100, holding the top spot for a record-breaking 13 weeks at the time.

The song’s emotional depth and vocal harmonies earned it two Grammy Awards: Best R&B Performance by a Duo or Group with Vocals and Best R&B Song. It remains a classic in the R&B genre, resonating with listeners for its poignant portrayal of love and loss.

Nothing Compares 2 U by Sinéad O’Connor

Sinéad O’Connor’s rendition of “Nothing Compares 2 U” catapulted her to global fame in 1990, marking a defining moment in her career.

Originally written by Prince in 1984 and later recorded by The Family, the song remained relatively obscure until O’Connor’s powerful interpretation. Co-produced with Chris Birkett, her version stripped away ornate R&B elements, focusing on raw emotion and minimalist arrangements.

The haunting music video, directed by John Maybury, further amplified its impact. It featured O’Connor’s intense close-ups and emotional vulnerability. Her tears in the video, triggered by personal grief over her mother’s death, added a poignant layer that resonated deeply with audiences worldwide.

I Will Always Love You by Whitney Houston

“I Will Always Love You” holds a unique place in music history. It originated as a heartfelt country ballad written and first performed by Dolly Parton in 1974. However, it was Whitney Houston’s powerhouse rendition for the 1992 film The Bodyguard that catapulted the song to global fame.

Kevin Costner, who was both Houston’s co-star and co-producer of the film, played a pivotal role in selecting the song for Houston to cover. David Foster then reimagined the song as a pop ballad, which became an iconic part of the film’s soundtrack. Houston’s version topped the Billboard Hot 100 for 14 weeks, setting a record at the time, and achieved renewed popularity after her passing in 2012.

I Can’t Make You Love Me by Bonnie Raitt

Bonnie Raitt’s career-defining ballad “I Can’t Make You Love Me,” from her album “Luck of the Draw,” marked a significant milestone in her long and celebrated career. Released in 1991, the song became a chart success in the United States, climbing to No. 18 on the Billboard charts and gaining acclaim for its poignant lyrics and Raitt’s emotive delivery. In the UK, it entered the singles chart at No. 50, representing Raitt’s first appearance on the UK singles chart after decades in the music industry.

Co-written by Mike Reid and Allen Shamblin and featuring piano by Bruce Hornsby, “I Can’t Make You Love Me” has since become a timeless classic, covered by various artists, including George Michael, Prince, and Boyz II Men. Despite its modest UK chart performance, the song’s enduring appeal has solidified its place as one of Bonnie Raitt’s most cherished and acclaimed songs, resonating deeply with audiences worldwide.

Gives You Hell by The All-American Rejects

“Gives You Hell” by The All-American Rejects became a significant hit for the band, marking their most successful single. Released as the lead single from their third album, “When the World Comes Down,” the song achieved notable success on the charts, including being recognized by Billboard as the “Most Played Song of the Year” in 2009.

Lead vocalist Tyson Ritter described the song as a tongue-in-cheek anthem directed towards someone who has caused frustration or hardship, whether it’s a personal foe, authority figure, or anyone else perceived as an obstacle in life.

The lyrics reflect a defiant attitude of flipping off those who have wronged or challenged the protagonist, resonating with listeners for its relatable theme and catchy rock sound.

She’s Gone by Daryl Hall and Kohn Oates

The story behind Hall & Oates’ “She’s Gone” music video is a fascinating glimpse into the early days of music videos, long before MTV and YouTube. In 1973, when music videos weren’t a standard promotional tool, Hall & Oates decided to create their own video for “She’s Gone” after refusing to lip-sync on a local TV show. The video was shot in a single take using props from their own apartment and costumes, including John Oates in a rented penguin suit with flippers and Daryl Hall in a bathrobe.

The unconventional video, directed by Oates’s sister, who was a film student at the time, featured surreal elements like a red-sequined devil and scattered Monopoly money set against a backdrop resembling a dentist’s waiting room. The TV station didn’t understand their approach and refused to air the video, leading to tensions and threats from the station and record company.

Despite the initial rejection, the video remained unseen for years until the advent of platforms like YouTube, where it eventually gained recognition as a cult classic. After reflecting on the experience, John Oates acknowledges the video’s ahead-of-its-time nature and the mixed reactions it continues to evoke.

Today, “She’s Gone” stands as a testament to their early creativity and willingness to defy conventional norms in the music industry.
As for recreating the magic with Saxsquatch at Oates Song Fest 7908, Oates hints at the possibility of revisiting such ideas in the future, keeping the spirit of experimentation alive even decades later.

Tears Dry by Amy Winehouse

Amy Winehouse’s song “Tears Dry On Their Own” holds a poignant backstory that reflects her personal experiences and artistic collaboration with producer Salaam Remi. Written in Miami, the song captures Winehouse’s feelings about a relationship she knew wouldn’t last. In an interview with the BBC, she described it as a reflection of being upset but knowing she would eventually move on.

The track cleverly samples Marvin Gaye and Tammi Terrell’s classic “Ain’t No Mountain High Enough,” originally a slower tempo. Remi envisioned a more upbeat, Motown-inspired tempo for Winehouse’s song after hearing the original instrumentals, which added a vibrant energy to the composition.

During the creative process, Remi recounted challenges in recording Winehouse’s vocals for the upbeat tempo. He mentioned that Winehouse, typically known for nailing her vocals quickly, experienced frustration trying to match the new sample’s tempo and style. Despite this rare struggle, once they achieved the right vocal performance, it transformed the song, highlighting the emotional depth and resilience conveyed in “Tears Dry On Their Own.”

Overall, the song stands as a testament to Winehouse’s ability to blend personal vulnerability with musical innovation, creating a timeless piece that resonates deeply with listeners.

Yesterday by Beatles

“Yesterday” by the Beatles is a poignant acoustic ballad depicting heartache from a relationship’s end. Written solely by Paul McCartney, its melancholic tone and introspective lyrics reflect loss and nostalgia. McCartney’s solo performance, accompanied by a string quartet, underscores the song’s emotional depth.

Despite its initial departure from the Beatles’ usual style, it became a chart-topping hit in the US and garnered widespread acclaim. With over 2,200 cover versions, it remains a timeless classic, voted among the best songs of the 20th century. Its enduring popularity attests to its universal appeal in capturing themes of love, regret, and longing.

I Fall to Pieces by Patsy Cline

“I Fall to Pieces” by Patsy Cline, written by Hank Cochran and Harlan Howard, embodies a timeless country classic that initially faced challenges finding its place.

Recorded in 1960, it took six months to top the Billboard country chart, showcasing Cline’s emotive delivery and the song’s lasting appeal. Initially deemed too pop for the country by some and vice versa by others, its eventual success was driven by strategic promotion and cross-genre appeal.

Despite Cline’s reservations during recording, the song’s poignant lyrics and the Jordanaires’ backing vocals resonated deeply, ensuring its enduring legacy with multiple chart entries and numerous covers over the decades.

How Can You Mend a Broken Heart by Al Green

The seventh track on Al Green’s 1972 album “Let’s Stay Together” is “How Can You Mend a Broken Heart.” This song is a cover of the Bee Gees’ original from 1971. Al Green’s rendition has been featured on the soundtracks of several movies, including “Good Will Hunting” (1997), “The Virgin Suicides” (1999), “Notting Hill” (1999), and “The Book of Eli” (2010).
It is one of the classics that beautifully depicts the loss and heartbreak one experiences after a breakup.

It’s Too Late by Carole King

“It’s Too Late” is a gentle rock ballad by Carole King that narrates the end of a romantic relationship. It appears on King’s “Tapestry” album. The single, released in April 1971, topped the U.S. Billboard Hot 100 and was certified Gold by the RIAA. The Isley Brothers covered it in 1973, and Gloria Estefan released her version in 1995.

Possibly Carole King’s best-known song, “It’s Too Late,” faced tough competition. Released as a single, it reached the top of the charts in April 1971. Ironically, it was replaced at No. 1 by James Taylor’s rendition of another Carole King song, “You’ve Got a Friend.”

The song earned the Grammy for Record of the Year in 1972. It is one of the standout tracks on “Tapestry” and is one of the few songs on the album with lyrics by someone else—Toni Stern.

Lover, You Should Have Come Over by Jeff Buckley

“Lover, You Should’ve Come Over” is both a folk-pop and soul ballad. It lasts 6 minutes and 43 seconds, is written in 6/8 time and in D major, and has a tempo of 120 beats per minute. Buckley’s vocal range stretches from B3 to D6, spanning over two octaves. The song opens with a “droning, ethereal” harmonium segment.

The lyrics, influenced by Buckley and Rebecca Moore’s breakup, reflect a young man’s sorrow as he grows older, realizing that his behavior reveals a mindset he believes he should have outgrown. Critic and biographer David Browne calls the lyrics “confused and confusing” and the music “a languid beauty.”

Ivy by Frank Ocean

In “Ivy,” Frank Ocean looks back on his errors and examines a broken relationship. With Ocean’s singing over a melancholic backing track, “Ivy” is a sorrowful song that could be considered a follow-up to his 2012 single “Thinkin Bout You.”

Sections of the song show Ocean overwhelmed with tears and anger. In a November 2016 interview with The New York Times, Ocean mentioned changing his voice to make it sound younger to capture the feelings of young love better.

The song might be about Ocean’s first love, which he wrote about in his 2012 Tumblr open letter.

Ocean performed an early demo version of “Ivy” at the Auditorium der BMW Welt in Munich, Germany, on June 25, 2013, during the first show of his European California Live tour.

Back to Black by Amy Winehouse

Amy Winehouse collaborated with Mark Ronson to create one of the iconic tracks of the 2000s, “Back to Black.” Ronson, after meeting Winehouse and bonding over their shared love for 60s girl groups, quickly composed the song’s piano riff overnight.

Despite initial doubts, Winehouse approved of the collaboration, leading to further work together on her album. While Ronson shaped the song’s distinctive sound, the deeply personal lyrics about heartbreak and loss came entirely from Winehouse herself, inspired by her tumultuous relationship with Blake Fielder-Civil.

The song and its video, shot in black and white, poignantly capture Winehouse’s emotional turmoil and artistic depth.

Thank U, Next by Ariana Grande

Ariana Grande’s “Thank You, Next” is the lead single and title track of her fifth studio album. Released on November 3, 2018, just before an episode of Saturday Night Live, the song immediately gained attention due to a joke about Grande by her ex-fiancé, Pete Davidson, prompting Grande to express her displeasure on Twitter.

The track debuted at #1 on the Billboard Hot 100, marking her highest charting single and becoming the first by a lead female artist to debut atop the US charts since Adele’s “Hello” in 2015. Its music video, directed by Hannah Lux Davis, pays homage to early-2000s movies and broke records on YouTube for its views.

Formidable by Stromae

Stromae conceived the idea for the “Formidable” video while reflecting on an encounter with a homeless man in Brussels who asked him, “Tu te crois beau?” (“Do you think you’re good looking?”)

He envisioned portraying a drunk, broken man authentically in the real world, not in a staged setting. One morning, he ventured to Place Louise in Brussels, a known area for trouble, to immerse himself in the role, capturing genuine reactions from passersby and even the police using carefully placed hidden cameras. He beautifully expressed the feelings of loss and irrationality after a difficult breakup.

The video, released shortly after filming, became a sensation, earning Stromae acclaim and winning Best Clip at the 2014 Victoires de la Musique.

Heartless by Kanye West

“Heartless” debuted as a promotional single nearly three weeks before Kanye West’s album “808s and Heartbreak” officially dropped.

It soared to number 2 on the Billboard Hot 100 and also claimed the top spots on the Rhythmic and Hot Rap Songs charts. Certified 6x platinum, it is Kanye’s third highest-selling single, trailing only “Stronger” and “Gold Digger.”

In contrast to other artwork from the 808s era, the single’s minimalist design notably omits any heart-themed elements, aligning directly with its title “Heartless”.

Somebody That I Used to Know by Gotye

After making waves on the Australian charts in late 2011, Gotye’s poignant narrative of lost love gained traction in the United States throughout 2012 and 2013. “Somebody That I Used To Know” delves into the aftermath of a mutual breakup, in which one person experiences deep emotional pain while the other remains emotionally detached.

Moreover, Gotye’s breakout hit “Somebody That I Used to Know” has resurfaced on the Billboard charts over a decade after its original release. It shows how the classic song has now transitioned into a breakup anthem.

The track, now titled “Somebody (2024),” has been remixed by electronic music producers Chris Lake, Fisher, and Sante Sansone. This new version retains much of the original’s essence but introduces a new beat about a minute into the song.

“Somebody (2024)” debuted at No. 27 on the Hot Dance/Electronic Songs chart and No. 11 on the Dance/Electronic Digital Song Sales chart. Gotye and Kimbra, the original collaborators, are also credited on this remix, marking Gotye’s return to the charts after his 2012 success with the original track.

All Too Well by Taylor Swift

Taylor Swift’s extended version of “All Too Well” has sparked renewed interest, particularly because it references her past relationship with Jake Gyllenhaal.

Originally released on her Red album in 2012, Swift revisited the song on her re-recorded album, “Red (Taylor’s Version),” due to a change in ownership of her masters.

The 10-minute version includes new lyrics that delve deeper into the brief but impactful romance, which fans speculate is about Gyllenhaal. Swift’s narrative songwriting style, known for drawing from personal experiences, adds emotional depth to the song, making it resonate strongly with listeners. The accompanying short film further explores the song’s themes, starring Dylan O’Brien and Sadie Sink, and reinforces its poignant narrative of love and loss.

Black Lake by Bjork

The documentary about Björk’s “Black Lake” delves into the intricate technical processes behind the creation of the music video, shot over three days in Iceland by Andrew Thomas Huang and visual effects studio Wolf & Crow.

The video, a part of Björk’s album Vulnicura, symbolically portrays her grappling with heartbreak in a cave-like setting. Premiered at her MoMA retrospective in 2015, the ten-minute piece is visually striking, capturing Björk’s emotional journey post-breakup with artist Matthew Barney.

The documentary explores the innovative use of visual effects, including research into Icelandic fungi, highlighting the meticulous craftsmanship that brought Björk’s vision to life.

Someone Like You by Adele

Dan Wilson and Adele wrote “Someone Like You” together over two days at Harmony Studio in Hollywood, which was suggested by Rick Rubin. Adele came to the session with lyrics and a melody for the first half of the verse, inspired by her recent heartbreak. Wilson’s role was to keep the song simple and direct, focusing on composing the music and creating chord changes.

They collaborated smoothly without arguments, focusing on capturing Adele’s raw and vulnerable vocal performance. Initially intended as a demo, the song resonated deeply with listeners and made an emotional impact even in its early stages.

Despite expecting a larger production, the demo version of Adele’s album was well-received immediately after being played by her manager and mother, both of whom were moved to tears. Wilson emphasized the power of sharing song ideas and advised aspiring songwriters to write prolifically and seek opportunities to perform their work publicly to gain valuable feedback.

Need You Now by Lady Antebellum 

“Need You Now” by Lady Antebellum, co-written with Josh Kear, delves into late-night loneliness and longing, capturing the urge for connection through a spontaneous phone call. Initially contentious, the line “I’m a little drunk” remained, adding authenticity. Written in just a few hours during their first session together, the song swiftly became the album’s title track and lead single.

Its music video was shot at Toronto’s King Edward Hotel, portraying the band members navigating emotional landscapes. The song topped the Billboard Hot Country Songs chart for five weeks, reached number two on the Hot 100, and earned acclaim with multiple awards, selling over 5 million copies globally.

Driver’s License by Olivia Rodrigo

Olivia Rodrigo’s debut single “drivers license” is rumored to be a heartfelt ode to moving on from her past relationship with Joshua Bassett, who allegedly began dating Sabrina Carpenter.

The song centers on fulfilling a promise to get her driver’s license, symbolizing closure. Released with a poignant music video showing Rodrigo driving aimlessly, it blends raw emotion with poignant details. Rodrigo teased the song on Instagram multiple times before its January 2021 release, hinting at its personal significance.

Happier Than Ever by Billie Eilish

“Happier Than Ever” by Billie Eilish, released in 2021 as a single from her second studio album of the same name, combines emo, pop-punk, and jazz influences. The song expresses Eilish’s frustration with a toxic relationship, beginning softly with classical and bass guitars before evolving into a distorted pop-punk and rock production.

Co-written with producer Finneas O’Connell, it received acclaim for Eilish’s cathartic vocals and robust production, hailed by critics as one of her standout tracks. The song peaked at number 11 on the Billboard Hot 100 and won Song of the Year at the MTV Video Music Awards, and Song of the Year at Grammy Awards supported by a visually striking music video and acclaimed live performances.

Cry Me a River by Justin Timberlake

Justin Timberlake performed his song “Cry Me a River,” famously inspired by his breakup with Britney Spears, at the Fontainebleau Las Vegas opening in 2023.

Before singing, Timberlake prefaced with “No disrespect,” aiming to soften the song’s historical context. Originally released in 2002 post-split, the track hinted at infidelity and heartbreak. Timberlake, dressed in a white tuxedo jacket and black pants, intertwined the song with Nirvana’s “Smells Like Teen Spirit,” reshaping its lyrics.

Despite not directly mentioning Spears, the performance sparked discussions online. Some saw it as Timberlake’s indirect response to Spears’ recent revelations in her memoir.

All I Wanted by Paramore

“All I Wanted” by Paramore delves into raw emotion, blending heartache with hope in a plea from a soul familiar with love and loss.

It expresses a universal longing for someone or something to fill a void, captured vividly in lyrics like “All I wanted was you,” echoing the ache of desire beyond reach.

The song contrasts vulnerability with cynicism about life’s fairness and reflects on mundane routines tinged with absence.

It’s a poignant exploration of yearning and reminiscence, encapsulating the power of music to resonate deeply with the human experience.

Yeah Yeah Yeahs by Maps

The Yeah Yeah Yeahs’ debut album “Fever To Tell” is known for its aggressive energy, but its standout hit “Maps” diverges with a heartfelt ode from Karen O to her partner, Angus Andrew of Liars.

Karen O aimed to create a timeless love song, reflecting her romantic nature amidst the challenges of touring life, where both artists were frequently on the road. The chorus, “They don’t love you like I love you,” struck a chord with listeners, propelling the song to success after initial singles flopped.

The song’s repetition mirrors the relentless cycle of tour life, capturing O’s genuine longing and emotional intensity.

Sometime Around Midnight by The Airborne Toxic Event

“Sometime Around Midnight” by Airborne Toxic Event highlights emotional depth and storytelling. The song lacks a traditional chorus, relying instead on building verses and layered instrumentation to intensify its narrative.

The lyrics evoke a universal experience of heartbreak, with vivid imagery portraying a chance encounter with an ex-lover at a bar.

The protagonist’s stream-of-consciousness reveals inner turmoil and longing, underscored by the poignant repetition of “You just have to see her.” Ultimately, the song portrays a futile search for closure, resonating deeply with listeners through its raw emotion and relatable themes.

Bye Bye Bye by NSYNC

‘Bye Bye Bye’ by NSYNC, written by Kristian Lundin, Jake Schulze, and Andreas Carlsson, is celebrated as one of the greatest breakup anthems. Carlsson was inspired by his own breakup while writing the song.

Despite its apparent theme of a failed relationship, many fans believe the song also symbolizes NSYNC’s split from their manipulative manager, Lou Pearlman. The band’s legal battle with Pearlman, who had restricted their earnings, adds a deeper layer to the song’s message, making it resonate as a declaration of independence and a fresh start.

Don’t Think Twice It’s Alright by Bob Dylan

Dylan clarified that the track is not a love song but a self-reflective statement, written after his girlfriend Suze Rotolo left for Italy. Rotolo, seen on the cover of *The Freewheelin’ Bob Dylan*, passed away in 2011.

Peter, Paul and Mary, The Four Seasons, Kesha, Willie Nelson, Merle Haggard, Glen Campbell, and Johnny Cash all covered the song. Kesha’s version was deeply emotional, while Campbell’s included guitar work by producer Carl Jackson due to Campbell’s Alzheimer’s. Rotolo revealed the line about a rooster crowing was inspired by their apartment near a poultry supplier.

Skinny Love by Bon Iver

Bon Iver’s “Skinny Love” is often misinterpreted as being about eating disorders, but founder Justin Vernon revealed its true meaning in a Pitchfork interview. The song focuses on heartbreak, capturing a phase in a failing relationship where one stays out of necessity rather than genuine affection. “Skinny love” symbolizes a fragile, insubstantial relationship. The emotional pain in the song arose from Vernon’s breakup with his girlfriend, Christy Smith.

Featured on their debut album, “For Emma, Forever Ago”, the track reflects Vernon’s personal turmoil and his plea for the relationship to endure despite its inevitable end.

Piece of My Heart by The Holding Company

“Piece of My Heart” is about a woman so deeply in love that she endures repeated heartbreak, offering her heart to her partner despite the pain. Janis Joplin’s powerful vocals perfectly capture the song’s emotional intensity, making her version iconic. Written by Jerry Ragovoy and Bert Berns, the song was first recorded by Erma Franklin in 1967.

Joplin’s rendition with Big Brother & the Holding Company became a major hit, showcasing her vocal prowess and leaving a lasting legacy long after her untimely death.

Dreaming with a Broken Heart by John Mayer

John Mayer’s “Dreaming With a Broken Heart” captures the anguish of waking up to the reality of lost love. The lyrics describe the painful shift from a dream, where the loved one feels present, to the harsh truth of their absence. The opening line, “When you’re dreaming with a broken heart, the waking up is the hardest part,” sets a sorrowful tone.

The imagery of rolling out of bed and falling to one’s knees depicts the physical pain of grief. The song highlights the struggle to accept the loss, with Mayer’s soulful delivery and melancholic melody enhancing its emotional impact.

Love Will Tear Us Apart by Joy Division

Joy Division’s “Love Will Tear Us Apart” poignantly captures the emotional disintegration of lead singer Ian Curtis, reflecting his troubled marriage and inner turmoil.

The song juxtaposes a haunting bass melody with svelte keyboards, highlighting Curtis’s resigned baritone. The lyrics explore the pain and inevitability of a relationship’s end, making it a timeless anthem of heartache.

Curtis’s tragic suicide in 1980, shortly after the song’s release, added depth to its meaning, solidifying its place in music history as both an epitaph for Curtis and a profound reflection on love’s destructive power. The title is engraved on Curtis’s gravestone, underscoring its lasting impact.

Believe by Cher

Cher’s hit “Believe” is an empowering anthem about moving on from a broken relationship. Its iconic chorus, “Do you believe in life after love?” became a defining moment in Cher’s career, showcasing her resilience and ability to reinvent herself.

The song’s use of Auto-Tune created a signature sound that left a lasting impact on the music industry, opening the door for its widespread use. Released when Cher was 52, “Believe” topped charts globally, challenging ageism and misogyny in pop music. It remains one of the best-selling singles of all time and solidified Cher’s status as a music legend.

Ex-Factor by Lauryn Hill

Lauryn Hill’s “Ex-Factor” is a poignant exploration of a tumultuous romantic relationship. The song delves into the complexities of love, where deep affection is marred by hurt and a lack of mutual respect. Hill’s lyrics express the frustration of being in a relationship that is both cherished and damaging, highlighting the emotional scars it leaves behind.

The chorus questions the dynamics of the relationship, suggesting an imbalance in emotional investment and a lack of reciprocity. Hill’s plea for fairness and mutual respect underscores the recognition of her worth and effort in the relationship, making “Ex-Factor” a powerful anthem for anyone who has experienced the heartache of a deeply flawed love.

Always on My Mind by Willie Nelson

“Always On My Mind” is a poignant song about a man expressing regret for not showing enough appreciation for his partner, despite always thinking of her. It reflects the complexities of love and regret, capturing a heartfelt apology.
Willie Nelson’s 1982 version became the definitive rendition, earning critical acclaim and numerous awards. Elvis Presley’s and the Pet Shop Boys’ versions also brought the song widespread recognition.

The song’s universal theme of love, regret, and longing has resonated across different genres and generations, making it a timeless classic.

Cry Me a River by Julie London

Julie London’s voice and persona transport listeners to smoky, intimate nightclubs, embodying a musical milieu like few others.

Known for her breathy, sultry style, she debuted in 1955 with “Cry Me a River,” a song about breakup that became a massive hit and propelled her career.

Despite describing her voice as “thimbleful,” London’s nuanced performances set her apart, making every song uniquely hers. She took on challenging material, from standards to contemporary hits, leaving an indelible mark on music.

Though she stopped recording in 1969, her influence persists, and her albums continue to captivate new audiences.

You’ve Lost that Lovin Feeling by The Righteous Brothers

“You’ve Lost That Lovin’ Feelin'” holds the record for the most plays on American radio and TV in the 20th century, surpassing 8 million broadcasts.
Written by Barry Mann and Cynthia Weil at Phil Spector’s request for The Righteous Brothers, it became a #1 hit and showcased Spector’s “Wall of Sound” production. Despite initial doubts, the song’s deep intro by Bill Medley and intricate vocal arrangement captivated audiences.

Covered by many, including Elvis and Hall & Oates, its enduring popularity led to multiple UK Top 10 appearances, notably in 1965, 1969, and 1990. It remains a timeless classic of soulful longing and musical innovation.

I Just Don’t Know What to Do with Myself by The White Stripes

The White Stripes’ “I Just Don’t Know What to Do with Myself” captures the disorientation and heartache following a breakup. The repeated line emphasizes the singer’s confusion and aimlessness after losing a significant other. Activities that once brought joy now bring sadness, highlighting the relationship’s impact on his life. The metaphor of a summer rose needing sun and rain illustrates his dependence on his partner’s love.

The band’s raw, garage rock and blues-influenced style enhances the song’s emotional intensity, making it a poignant anthem for those experiencing the emptiness of a lost relationship.

Dry Your Eyes by The Streets

“Dry Your Eyes” by The Streets is a heartfelt song from the concept album “A Grand Don’t Come For Free,” detailing the narrator’s painful breakup. The lyrics convey raw emotion, urging the narrator to move on despite the heartbreak.

The song features a string sample that songwriter Michael Gagliano claimed was from his composition, though Mike Skinner stated it came from a public domain library.

Coldplay’s Chris Martin originally sang the chorus, but his version was never released as another vocalist’s take was preferred. The track is noted for its emotional depth and musical innovation.

(Habits) Stay High by Tovar Lo

In “Habits (Stay High),” the narrator describes using unhealthy behaviors to cope with a breakup.

This raises the question: is the narrator Tove Lo herself or a fictional character? In interviews, Tove Lo explains the song is about a real relationship and her own mistakes, emphasizing that her lyrics are drawn from her life and experiences without censorship.

While she admits that singing about her actions is easier than discussing them, she maintains honesty in her music.

Although the song appears autobiographical, Lo is careful not to make explicit statements about illegal activities, suggesting that while emotionally honest, some details might be exaggerated.

Shoutout to My Ex by Little Mix

Little Mix’s song “Shout Out to My Ex” seems to reference past relationships, though the group avoids naming names.

In an interview on ‘The Today Show,’ when asked about the song’s inspiration, Perrie Edwards stayed silent while Jesy Nelson explained that the song aims to be relatable to everyone who has dealt with a difficult ex, empowering listeners to feel independent and strong.

While it’s easy to speculate about whom the verses might reference based on the members’ lives, the band maintains a classy approach by not confirming any specific details.

The Man Who Cannot be Moved by The Script

The Script’s “The Man Who Can’t Be Moved,” released in 2008, became a hit from their debut album. In an interview with Smooth Radio, Danny O’Donoghue revealed the song emerged late in their album’s production, inspired by a sense of uncertainty.

It tells a story similar to “Forrest Gump,” in which a protagonist waits at a significant spot for an ex-lover, hoping for reconciliation.

Mark Sheehan noted the song’s bridge about fame reflected their personal experiences without directly naming their exes.

The song’s popularity was underscored by covers from artists like Ed Sheeran, and its music video, filmed in Downtown Los Angeles, symbolizes unwavering hope amidst passing time.

That concludes the extensive list of 65 best breakup songs of all time. They have a special place in history, some receiving memorable accolades while others remain relatable today.