Entertainment Music 75 Best Breakup Songs Of All Time Share PINTEREST Email Print Kevin Winter / Getty Images Music Pop Music Top Picks Basics Reviews Top Artists 80s Hits 90s Hits Rock Music Alternative Music Classical Music Country Music Folk Music Rap & Hip Hop Rhythm & Blues World Music Punk Music Heavy Metal Jazz Latin Music Oldies Learn More By Bill Lamb Bill Lamb Bill Lamb is a music and arts writer with two decades of experience covering the world of entertainment and culture. Learn about our Editorial Process Updated on 05/24/19 Breakup songs occupy a key segment of the overall spectrum of love songs. They can range from resigned sadness to outright anger. These are 75 of the best expressions of the experience of breaking up in song. 75 of 75 The Police - "Every Breath You Take" (1983) The Police - "Every Breath You Take". A&M Inspired by Sting's divorce from Frances Tomelty, "Every Breath You Take" details stalking an ex-lover. Sting has admitted being somewhat disturbed by those who see it as a positive love song when in fact it is ugly and sinister. "Every Breath You Take" spent eight weeks at the top of the US pop chart and won the Grammy Award for Song of the Year. 74 of 75 Toni Braxton - "Un-Break My Heart" (1996) Toni Braxton - "Un-Break My Heart". LaFace Written by Diane Warren, "Un-Break My Heart" details the emotions following a bitter breakup and expresses the desire for the lover to return and undo the pain caused. Toni Braxton originally did not want to record the song, but L.A. Reid convinced her to change her mind. "Un-Break My Heart" spent 11 weeks at #1 on the Billboard Hot 100 becoming one of the biggest hits of all time. It won the Grammy Award for Best Female Pop Vocal. 73 of 75 Willie Nelson - "Always On My Mind" (1982) Willie Nelson - Always On My Mind. Columbia The wistful "Always On My Mind" is one of the most recorded songs written in the last 50 years. Primary songwriter Wayne Carson finished most of it in 10 minutes at his kitchen table. Johnny Christopher and Mark James helped work out a bridge in the studio, and "Always On My Mind" was complete. The top 5 pop charting Willie Nelson recording was the first visit of the song to the pop top 10 and earned a Grammy Award for Song of the Year. Three years later Pet Shop Boys returned "Always On My Mind" to the pop top 10. 72 of 75 Barry Manilow - "Even Now" (1978) Barry Manilow - Even Now. Arista Barry Manilow's top 20 pop hit "Even Now" occupies a relatively unique niche among breakup songs in its discussion of the lingering pain of a breakup even after both partners have moved on to new relationships. Barry Manilow co-wrote the song with Marty Panzer, a frequent songwriting partner early in his career. 71 of 75 Daryl Hall & John Oates - "She's Gone" (1976) Daryl Hall and John Oates - "She's Gone". Atlantic In its initial release the Daryl Hall and John Oates classic "She's Gone" had only mild success peaking at #60 on the Billboard Hot 100 in 1974. However, following the top 10 breakthrough of "Sara Smile," the song was re-released and it climbed all the way to #7. "She's Gone" was also a #1 R&B hit for the band Tavares. 70 of 75 Nelly - "Just a Dream" (2010) Nelly - "Just a Dream". Universal Motown Many fans thought that the breakup song "Just a Dream" was about the end of rapper Nelly's 9-year relationship with singer Ashanti. However, he claims that is not true, and the song is more universal. "Just a Dream" reached #3 on the pop singles chart becoming Nelly's highest charting hit in 5 years 69 of 75 Connie Francis - "Who's Sorry Now" (1958) Connie Francis - "Who's Sorry Now". MGM "Who's Sorry Now?" was first written and published in 1923. It was included in the 1946 Marx Brothers film A Night In Casablanca. It was recorded by a wide range of artists through the years. However, it is Connie Francis' last-minute recording that turned into her breakthrough top 5 smash that has been recognized as the standard. 68 of 75 Tove Lo - "Habits (Stay High)" (2014) Tove Lo - "Habits (Stay High)". Universal Swedish singer Tove Lo introduced herself to worldwide pop audiences with the honest, intense song about the aftermath of a broken love relationship. She has said the song "Habits" was written immediately after a breakup and the details on use of drugs to forget are true. 67 of 75 Elton John - "Sorry Seems To Be the Hardest Word" (1976) Elton John - "Sorry Seems To Be the Hardest Word". MCA After a whirlwind of massive success in the mid-1970's, it seemed that Elton John was growing a bit weary, and his double album Blue Moves reflected that. It uncharacteristically missed hitting #1 on the album chart, but the lead single, the melancholy breakup song "Sorry Seems To Be the Hardest Word," hit the top 10 and has endured as a fan and critical favorite. 66 of 75 Linda Ronstadt - "You're No Good" (1974) Linda Ronstadt - Heart Like a Wheel. Capitol Written by Clint Ballard, Jr., "You're No Good" has its origins in the early 1960s. R&B singer Betty Everett released a single version in 1963 and it became a top 10 R&B hit. Having already used the song in concert, Linda Ronstadt decided at the last minute to record "You're No Good" for her album Heart Like a Wheel. It was released as the lead single from the album and became Linda Ronstadt's breakthrough hit and her only #1 single. 65 of 75 Bill Withers - "Ain't No Sunshine" (1971) Bill Withers - "Ain't No Sunshine". A&M Soul singer-songwriter Bill Withers says he was inspired to write "Ain't No Sunshine" after seeing the 1962 film Days of Wine and Roses. He came up with the concept, "Sometimes you miss things that weren't particularly good for you." "Ain't No Sunshine" is also notable for repeating the phrase, "I know," 26 times. DJ's flipped over Bill Withers' single "Harlem" for this song on the B-side and it became the singer-songwriter's first top 10 hit winning a Grammy Award for Best R&B Song. 64 of 75 Neil Sedaka - "Breaking Up Is Hard To Do" (1962) Neil Sedaka - "Breaking Up Is Hard To Do". RCA "Breaking Up Is Hard To Do" remains the only song to have been recorded by the same artist in two vastly different versions hitting the pop top 10 both times. Singer-songwriter Neil Sedaka hit #1 with an uptempo pop recording of "Breaking Up Is Hard To Do" in 1962. 13 years later he re-recorded the hit as a slow ballad and climbed to #8 in December 1975. 63 of 75 Nazareth - "Love Hurts" (1975) Nazareth - "Love Hurts". A&M Written by country-pop songwriter Boudleaux Bryant, "Love Hurts" was first recorded by the Everly Brothers in 1960. Roy Orbison had a pop hit in Australia with his version of the song in 1961. However, it is the hard rock band Nazareth who turned the ballad into a breakup classic. The group's version of "Love Hurts" reached the pop top 10 in 1976. 62 of 75 Phil Collins - "Against All Odds (Take a Look At Me Now)" (1984) Phil Collins - "Against All Odds (Take a Look At Me Now)". Atlantic "Against All Odds" began as a song titled "How Can You Just Sit There?" which Phil Collins wrote after his first wife left him. It didn't make the cut for the 1981 album Face Value and was then reworked specifically for the movie Against All Odds. The song about the desire for reconciliation after a breakup won a Grammy Award for Best Pop Male Vocal and received a nomination for Song of the Year. It also received a Best Song nomination at the Academy Awards. 61 of 75 Katy Perry - "Part Of Me" (2012) Katy Perry - "Part Of Me". Capitol "Part Of Me" was initially written during the sessions that ultimately resulted in the album . Clearly depicting a breakup, it seems the song was likely first written about Katy Perry's relationship with Travie McCoy. However, the recording was not finalized and released until the deluxe reissue of Teenage Dream. At that point, Katy Perry had separated from her husband Russell Brand. However, she claims the song is definitely not about her marriage. 60 of 75 Frank Ocean - "Thinkin' Bout You" (2012) Frank Ocean - "Thinkin' Bout You". Def Jam "Thinkin' Bout You" is a complex song from Frank Ocean's debut album Channel Orange. It received strong critical acclaim and climbed to #32 on the Billboard Hot 100. The song was first written to be recorded by Bridget Kelly, and her version is titled "Thinking About Forever." Frank Ocean decided to record his own take on the song because the content remained strongly personal. 59 of 75 Roxette - "It Must Have Been Love" (1990) Roxette - "It Must Have Been Love". EMI While Swedish duo Roxette were riding the success of their #1 hits "The Look" and "Listen To Your Heart," they were asked to contribute a song to the soundtrack of the movie Pretty Woman. Used as breakup music in the soundtrack, "It Must Have Been Love" became the biggest hit song from the movie spending two weeks at #1 on the Billboard Hot 100. 58 of 75 Rolling Stones - "Angie" (1973) Rolling Stones - Goats Head Soup. Rolling Stones Records Through the years there has been much speculation about the actual subject matter of the Rolling Stones' breakup song "Angie." Some believed it was about David Bowie's wife Angela or actress Angie Dickinson. Mick Jagger and Keith Richards have given sometimes conflicting stories including Keith Richards' claim that "Angie" was a code name for heroin and his efforts to quit. The melancholy ballad was a #1 pop hit for the group. 57 of 75 Coldplay - "The Scientist" (2002) Coldplay - "The Scientist". Capitol Coldplay lead vocalist Chris Martin has said "The Scientist" is simply "about girls." The piano ballad has become a Coldplay classic. It was a top 10 pop hit in the UK and climbed into the top 20 on the US alternative songs chart. 56 of 75 Pink - "So What" (2008) Pink - "So What". LaFace In January 2006 Pink married motocross racer, Carey Hart. In February 2008 she announced that they had separated. Released in August 2008, "So What" depicts Pink's side of the relationship. The song became Pink's first solo #1 pop hit. The story has a happy ending as Pink and Carey Hart reunited in January 2009. 55 of 75 Kanye West - "Heartless" (2008) Kanye West - "Heartless". Def Jam On "Heartless," Kanye West utilizes auto-tune to provide a specific feel to his singing. The song details his emotions following his breakup with fiancee Alexis Phifer just months after the passing of his mother Donda West. The song debuted at #4 on the Billboard Hot 100 and ultimately peaked at #2. 54 of 75 The Everly Brothers - "Cathy's Clown" (1960) Everly Brothers - Cathy's Clown. Warner Bros. Musically, the Everly Brothers' #1 pop smash "Cathy's Clown" was influenced by Ferde Grofe's Grand Canyon Suite. Lyrically, the brothers took the inspiration of stories about childhood taunting told by their father Ike Everly and created a devastating song about a protagonist who's masculinity is threatened by the mistreatment of his girlfriend Cathy. 53 of 75 Joy Division - "Love Will Tear Us Apart" (1980) Joy Division - "Love Will Tear Us Apart". Factory The anguished lyrics of "Love Will Tear Us Apart" are assumed to represent the difficult relationship between the band's lead vocalist Ian Curtis and his wife Deborah Curtis. The song was recorded just two months before Ian Curtis committed suicide in May 1980. "Love Will Tear Us Apart" was released as a single in June and became the group's first chart hit in the UK peaking at #13. It also climbed into the US dance chart. 52 of 75 Chicago - "If You Leave Me Now" (1976) Chicago - "If You Leave Me Now". CBS Following a break in new material for their first greatest hits collection, the band Chicago returned in 1976 with the big breakup ballad "If You Leave Me Now." It was written by group member Peter Cetera. He performed the lead vocal and the song became Chicago's first #1 hit single after 11 visits to the top 10. 51 of 75 ABBA - "The Winner Takes It All" (1980) ABBA - "The Winner Takes It All". Polar Many fans believe "The Winner Takes It All" is about the divorce between ABBA members Bjorn Ulvaeus and Agnetha Faltskog. However, Bjorn Ulvaeus denies that and says the song instead is one about the general experience of going through divorce. "The Winner Takes It All" became ABBA's fourth and last top 10 hit single in the US. 50 of 75 Brenda Lee - "I'm Sorry" (1960) Brenda Lee - "I'm Sorry". MCA After a 15-year-old Brenda Lee recorded "I'm Sorry," it was withheld from release for a few months, because it was considered that many would think she was too young to sing about such adult emotions. However, the simple, emotional ballad went straight to #1 becoming a signature song for the Rock and Roll Hall of Fame member. It was one of the first records recorded in Nashville that featured strings. 49 of 75 The Platters - "Smoke Gets In Your Eyes" (1958) The Platters - "Smoke Gets In Your Eyes". Mercury "Smoke Gets In Your Eyes" had its origins as an uptempo leftover from Jerome Kern's classic Show Boat. Slowed down into a ballad it made its debut in the 1933 Broadway musical Roberta. It was revived in 1959 as a #1 pop hit by the vocal group the Platters. The achingly romantic lyrics describe the tears and laughter when true love has gone. 48 of 75 Fleetwood Mac - "Go Your Own Way" (1977) Fleetwood Mac - "Go Your Own Way". Warner Bros. Fleetwood Mac's legendary album Rumours is filled with songs about breakups and relationships in crisis. Lindsey Buckingham wrote "Go Your Own Way" about his relationship with Stevie Nicks. One of the most memorable lines, "Packing up, shacking up is all you want to do." Stevie Nicks asked for it to be removed, and Lindsey Buckingham refused. "Go Your Own Way" became Fleetwood Mac's first top 10 pop hit single in the US. 47 of 75 Julie London - "Cry Me a River" (1956) Julie London - Cry Me a River. Liberty Originally written for Ella Fitzgerald in 1953, fortunately for Julie London, the jazz legend didn't get around to recording it until eight years later. Julie London's top 10 charting version became her signature song after its use in the film The Girl Can't Help It. The expression of bitterness after the end of a relationship has comforted many in similar situations. 46 of 75 Cee Lo Green - "F**k You" (2010) Cee Lo Green - "F**k You!". Elektra Despite the lyrics being presented in a form that references a romantic relationship, Cee Lo Green says the inspiration is actually his feelings about the music industry. The offensive word in the title caused a slightly altered version titled "Forget You" to be created for pop radio consumption. It was a smash hit climbing to #2 on the Billboard Hot 100 and earning Grammy Award nominations for Record and Song of the Year. 45 of 75 Thelma Houston - "Don't Leave Me This Way" (1976) Thelma Houston - "Don't Leave Me This Way". Motown "Don't Leave Me This Way" was first recorded by Harold Melvin and the Blue Notes in 1975. It was a top 5 pop hit in the UK and reached #3 on the US disco chart. However, it was Thelma Houston's 1976 cover that became a true classic topping both the pop and disco charts in the US. The song later gained even more poignancy with its attachment to the AIDS epidemic. The Communards brought "Don't Leave Me This Way" back to #1 on the dance chart in 1986. 44 of 75 Elvis Presley - "Heartbreak Hotel" (1956) Elvis Presley - "Heartbreak Hotel". RCA Songwriter Tommy Durden was inspired to begin writing the lyrics for "Heartbreak Hotel" after reading a newspaper article about a man who committed suicide leaving a note that read, "I walk a lonely street." Mae Boren Axton helped him complete the song and it was offered to Elvis Presley for recording to fulfill a promise. The result was a rock and roll classic which became Elvis Presley's first #1 pop hit. 43 of 75 J. Geils Band - "Love Stinks" (1980) J. Geils Band - Love Stinks. EMI "Love Stinks" expresses bitter disdain for the emotional pain caused by the end of relationships after being in love. It was a top 40 hit for the J. Geils Band and helped lead up to their massive success with the album Freeze Frame a year later. 42 of 75 Usher - "Burn" (2004) Usher - "Burn". Arista "Burn" appeared in the wake of Usher's breakup with TLC's Rozonda "Chilli" Thomas so many fans assumed the song was about them. However, producer Jermaine Dupri later stated much of the lyrical content of Usher's Confessions album was related to his personal life. Either way, the song was a #1 smash hit and received a Grammy Award nomination for Best R&B Song. 41 of 75 No Doubt - "Don't Speak" (1996) No Doubt - "Don't Speak". Interscope Romantic difficulties among group members have produced some of the greatest breakup music of all time. "Don't Speak" is one of those. It was written by No Doubt members Gwen Stefani and her brother Eric Stefani about the end of the relationship between Gwen Stefani and band member Tony Kanal. "Don't Speak" set a record by spending 16 consecutive weeks at #1 on pop radio in the US. It turned No Doubt into international pop superstars. 40 of 75 Natalie Imbruglia - "Torn" (1998) Natalie Imbruglia - "Torn". RCA The song "Torn" was first recorded by the alternative rock band Ednaswap in 1995. It was written two years earlier. However, it was a 1997 recording by Australian singer Natalie Imbruglia which turned it into a major hit. "Torn" hit the pop top 10 in countries around the world and climbed to #1 at mainstream pop radio in the US. 39 of 75 The Four Seasons - "Big Girls Don't Cry" (1962) Four Seasons - "Big Girls Don't Cry". Vee Jay Four Seasons songwriter and producer Bob Crewe says that "Big Girls Don't Cry" had its origins when he fell asleep while watching TV and awoke to hear the line, "Big girls don't cry" in the 1956 film Slightly Scarlet. Lyrically the song depicts the protagonist's anguish when his girl calls his bluff about breaking up and says the song's title. 38 of 75 Jackson 5 - "I Want You Back" (1969) Jackson 5 - "I Want You Back". Motown Sometimes a breakup seems like it occurred a little too hastily. That is the theme of the first hit by The Jackson 5. Fueled by a stellar lead vocal from 11-year-old Michael Jackson, "I Want You Back" went to #1, the first of four consecutive chart-toppers for the group. The recording has been inducted into the Grammy Hall of Fame. 37 of 75 Taylor Swift - "We Are Never Ever Getting Back Together" (2012) Taylor Swift - "We Are Never Ever Getting Back Together". Big machine After writing her entire album Speak Now on her own, Taylor Swift opted to collaborate with Max Martin and Shellback on "We Are Never Ever Getting Back Together." The song grew out of a rumor that Taylor Swift was reuniting with an ex-boyfriend. It was Taylor Swift's first #1 pop hit and received a Grammy Award nomination for Record of the Year. 36 of 75 Justin Timberlake - "Cry Me a River" (2002) Justin Timberlake - "Cry Me a River". Jive From 1999 through early 2002, Justin Timberlake and Britney Spears were one of the hottest of young celebrity couples. After a particularly difficult phone call in the break-up process, "Cry Me a River" was born. A review in Rolling Stone referred to the song as a "breakup aria." The song was a #3 charting pop smash and helped establish Justin Timberlake as a serious solo artist. His performance earned a Grammy Award for Best Pop Male Vocal. 35 of 75 Lady Antebellum - "Need You Now" (2009) Lady Antebellum - Need You Now. Capitol Nashville Country trio Lady Antebellum touched a familiar chord with many music fans across the country and pop spectrum with "Need You Now's" description of a desperate late night phone call to a former lover. There was initial record label concern about the line, "I'm a little drunk," but it was left one and gives a strikingly honest feel to the song. "Need You Now" won Grammy Awards for Record and Song of the Year. 34 of 75 Paul Simon - "50 Ways To Leave Your Lover" (1975) Paul Simon - "50 Ways To Leave Your Lover". Columbia Paul Simon wrote "50 Ways To Leave Your Lover" following his divorce from his first wife Peggy Harper. The song incorporates humor into the breakup song genre as it discusses a list of options in ending a relationship. The song was a #1 smash hit, Paul Simon's only solo hit to go all the way to the top. It is included on the album Still Crazy After All These Years which won the Grammy Award for Album of the Year. 33 of 75 Bonnie Tyler - "Total Eclipse Of the Heart" (1983) Bonnie Tyler - Faster Than the Speed Of Night. Columbia Written by Jim Steinman, best known for his work on Meat Loaf's breakthrough album Bat Out of Hell, "Total Eclipse of the Heart" is awash in grand pronouncements about the darkness of love fading away. Jim Steinman says it was inspired by vampires. The song became a #1 pop smash and a defining moment in singer Bonnie Tyler's career. 32 of 75 Greg Kihn Band - "The Breakup Song (They Don't Write 'Em)" (1981) The Greg Kihn Band - "The Breakup Song (They Don't Write 'Em)". Beserkley Greg Kihn's breakthrough hit single "The Breakup Song" both laments a recent breakup and celebrates great breakup songs of the past. It was the artist's first song to reach the Billboard Hot 100 and it climbed all the way to #15. It was followed in 1983 by the Greg Kihn Band's biggest hit, the #2 pop smash "Jeopardy." 31 of 75 Beyonce - "Irreplaceable" (2006) Beyonce - "Irreplaceable". Columbia Ne-Yo originally wrote lyrics for "Irreplaceable" from a male perspective and in the style of a country song. However, when Beyonce heard a demo, she thought it was a great opportunity to create a breakup record that women could relate to. "Irreplaceable" was a #1 pop smash and received a Grammy Award nomination for Record of the Year. 30 of 75 A Great Big World - "Say Something" featuring Christina Aguilera (2013) A Great Big World - Say Something featuring Christina Aguilera. Epic "Say Something" depicts the powerful emotions when one chooses to leave a relationship even though love remains. Following Christina Aguilera's decision to add her voice to the mix in a re-recording of the song, "Say Something" stormed up the charts to become a top 5 hit. 29 of 75 Nancy Sinatra - "These Boots Are Made For Walkin'" (1966) Nancy Sinatra - "These Boots Are Made For Walkin'". Reprise As legend states, songwriter Lee Hazlewood told Nancy Sinatra to sing his song "These Boots Are Made For Walkin'" in such a fashion so that she would sound like, "a 16-year-old girl who f**ks truck drivers." The song was an instant success becoming the only solo #1 pop hit by Frank Sinatra's daughter Nancy. 28 of 75 Dionne Warwick - "Walk On By" (1964) Vogue Schallplatten For some listeners, the elegant production of Dionne Warwick's performance of "Walk On By" hides the devastating heartbreak in the song's lyrics. However, that is one of the points of the song. The former lover does not deserve to see the heartbreak. The song became Dionne Warwick's biggest hit of her career so far peaking at #6. It has been re-recorded numerous times by artists as diverse as punk band The Stranglers and soul legend Isaac Hayes. 27 of 75 Diana Ross - "Touch Me In the Morning" (1973) Diana Ross - "Touch Me In the Morning". Motown Co-songwriter and producer Michael Masser says that Diana Ross pushed very hard in the studio to come up with exactly the right emotional tone for this breakup song. He says it was a very intense experience. The effort paid off in a #1 hit and one of Diana Ross' signature songs. 26 of 75 Bonnie Raitt - "I Can't Make You Love Me" (1991) Bonnie Raitt - "I Can't Make You Love Me". Capitol Nashville songwriters Mike Reid and Allan Shamblin took more than six months to write the aching ballad. Bonnie Raitt recorded it for her album Luck of the Draw with piano support from Bruce Hornsby. "I Can't Make You Love Me" became a top 20 pop hit. George Michael, Boyz II Men, and Adele have all recorded notable cover versions. 25 of 75 Bee Gees - "How Can You Mend a Broken Heart" (1971) Bee Gees - "How Can You Mend a Broken Heart". Polydor In December 1969, the Bee Gees, the three Gibb brothers Barry, Robin, and Maurice, all went their separate ways. It seemed the group was over, but in August 1970, Barry and Robin began writing songs together again. "How Can You Mend a Broken Heart" was one of those. It became the group's first #1 pop hit in the US. The song was used in a key role on the soundtrack to the 2013 movie American Hustle. 24 of 75 Boyz II Men - "End of the Road" (1992) Boyz II Men - "End Of the Road". Motown L.A. and Babyface along with Daryl Simmons co-wrote and co-produced "End of the Road" for Boyz II Men. It was included on the soundtrack for the Eddie Murphy movie Boomerang. The soulful and mournful ballad about the end of a relationship spent a then-record 13 weeks at the top of the Billboard Hot 100 and won the Grammy Award for Best R&B Song. 23 of 75 Patsy Cline - "I Fall To Pieces" (1961) Patsy Cline - "I Fall To Pieces". Decca The emotional classic "I Fall To Pieces" had a difficult time coming to fruition. It was first turned down by Brenda Lee for being too country. Rising artist Roy Drusky then turned it down for not being a "man's song." Patsy Cline asked to record it, but she became distressed by the pop arrangement planned for the record. Radio stations were slow to play the record, but it ultimately became a classic topping the country chart and reaching #12 on the pop chart 22 of 75 Cher - "Believe" (1998) Cher - "Believe". Warner Bros. "Do you believe in life after love?" That is a question many likely ask themselves in the midst of a difficult break-up, and it is the key line for Cher's #1 smash hit "Believe." The song is known for its innovative use of auto-tune effects on the vocals. "Believe" returned Cher to the top of the pop singles chart in the US for the first time in 24 years. 21 of 75 Gilbert O'Sullivan - "Alone Again (Naturally)" (1972) Gilbert O'Sullivan - Alone Again (Naturally). MAM Irish singer Gilbert O'Sullivan became an international pop star with this emotionally intense breakup ballad. It kicks off with suicidal thoughts after having been left at the altar. Pop fans assumed the song was autobiographical, but Gilbert O'Sullivan pointed to his own personal life details to show that it was not. "Alone Again (Naturally)" was a #1 pop hit and received Grammy Award nominations for Record and Song of the Year. 20 of 75 Roy Orbison - "Crying" (1961) Roy Orbison - "Crying". Monument Few songs aside from "Crying" so directly address the emotional breakdown after a breakup. Rock and roll legend Roy Orbison took the song all the way to #2 on the Billboard Hot 100. Joe Melson co-wrote the song with Roy Orbison, and they had previously written the hits "Only the Lonely" and "Running Scared." Singer-songwriter Don McLean took "Crying" back to the pop top 10 in 1981. 19 of 75 Harry Nilsson - "Without You" (1971) Harry Nilsson - "Without You". RCA Badfinger group members Pete Ham and Tom Evans co-wrote "Without You" in response to real life events they each experienced. It was recorded for the group's album No Dice but not released as a single. Harry Nilsson heard the song at a party and decided to record his own version. It reached #1 on pop charts, and "Without You" has become a frequently recorded classic. Mariah Carey took it to #3 in 1994. 18 of 75 Gotye - "Somebody That I Used To Know" featuring Kimbra (2012) Gotye - "Somebody That I Used To Know" featuring Kimbra. Eleven Singer-songwriter Gotye says that "Somebody That I Used To Know" was drawn from a variety of his experiences in relationships breaking up. He says that he added the female part sung by New Zealand's Kimbra because otherwise, the song felt weak. The result was a worldwide pop smash hitting #1 in the US as well. It won the Grammy Award for Record of the Year. 17 of 75 Bob Dylan - "Tangled Up In Blue" (1975) Bob Dylan - Blood On the Tracks. Columbia "Tangled Up In Blue" has been celebrated as containing a brilliant song lyric about the ending of love while standing outside of normal notions of time and space. Bob Dylan's way of combining multiple perspectives in a single song was influenced by his study of Cubist art. "Tangled Up In Blue" is included on the album Blood On the Tracks. 16 of 75 Wham! - "Careless Whisper" featuring George Michael (1984) Wham! - "Careless Whisper" featuring George Michael. Columbia George Michael and Andrew Ridgeley, the members of the duo Wham!, wrote "Careless Whisper" together long before they became pop stars. George Michael has said that he wrote the lyric line in a flippant mood, and was disillusioned by the fact that it became meaningful to so many fans. The song was a #1 pop smash on both sides of the Atlantic. 15 of 75 Robyn - "Dancing On My Own" (2010) Robyn - "Dancing On My Own". Konichiwa Robyn said that the inspiration for "Dancing On My Own" grew out of her love of sad, gay disco anthems by artists like Donna Summer and Sylvester. The song depicts the protagonist standing alone watching her ex-lover dance with someone new. "Dancing On My Own" reached #3 on the dance chart in the US and received a Grammy Award nomination for Best Dance Recording. 14 of 75 Bruno Mars - "Grenade" (2010) Bruno Mars - "Grenade". Atlantic The Smeezingtons, Bruno Mars' team of producers and songwriters, say the key to "Grenade" is the closing, "But you won't do the same." It took them two months to come up with the line which seals the song. "Grenade" became a #1 smash hit single and received Grammy Award nominations for Record and Song of the Year. 13 of 75 Amy Winehouse - "Back To Black" (2007) Amy Winehouse - "Back To Black". Island Amy Winehouse's relationship with Blake Fielder-Civil was the inspiration for "Back To Black." He left her for an ex-girlfriend which returned Amy Winehouse to depression and alcohol. The song was praised for both its emotional honesty and its use of elements of the 60s girl group sound. 12 of 75 The Miracles - "The Tracks Of My Tears" (1965) The Miracles - "The Tracks Of My Tears". Tamla The song "The Tracks Of My Tears" has its origins in the Marvin Tarplin guitar part which opens the recording. Lyrically, the song details efforts to hide heartbreak in public. A close look reveals, "The tracks of my tears." The recording has been inducted into the Grammy Hall of Fame. 11 of 75 Roberta Flack - "Killing Me Softly With His Song" (1973) Roberta Flack - Killing Me Softly. Atlantic The powerful words of "Killing Me Softly With His Song" began with singer-songwriter Lori Lieberman and her emotional response to seeing Don McLean perform live. Charles Fox and Norman Gimbel fleshed out the experience in a song that Lori Lieberman recorded for her self-titled debut album in 1972. However, it is Roberta Flack's soulful cover, recorded after she heard the original on a plane flight, that became a pop smash spending five weeks at #1. It won the Grammy Awards for Record and Song of the Year. The Fugees took the song back to the top of the charts in 1996. 10 of 75 Adele - "Someone Like You" (2011) Adele - "Someone Like You". Columbia Records Written with American songwriter Dan Wilson, "Someone Like You" was one of the last songs written for Adele's album 21. She says that after being exhausted writing angry songs like "Rolling In the Deep" about her recent relationship, she wanted a song that would help her feel OK about the two years with her ex-boyfriend. "Someone Like You" soared to #1 in the UK after a celebrated Brit Awards performance and later in the year reached #1 in the US as well. 09 of 75 Whitney Houston - "I Will Always Love You" (1992) Whitney Houston - "I Will Always Love You". Arista Dolly Parton first wrote and recorded "I Will Always Love You" as a track on her 1974 album Jolene. It was written about the professional breakup with Porter Wagoner. Released as a single, it went to #1 on the country chart. It went to #1 on the country chart again in 1982 when Dolly Parton re-recorded it for the soundtrack to the film The Best Little Whorehouse In Texas. The biggest hit version came in 1992 when Whitney Houston recorded "I Will Always Love You" for the soundtrack of The Bodyguard. It went to #1 on the Billboard Hot 100 for a then-record 14 weeks and won the Grammy Award for Record of the Year. 08 of 75 Carole King - "It's Too Late" (1971) Carole King - "It's Too Late". Ode Carole King's #1 solo smash hit "It's Too Late" takes a very adult look at the ending of a relationship. Included on the album Tapestry, it is a landmark in the early 1970s singer-songwriter movement. Toni Stern co-wrote the song with Carole King and says she put together the lyrics after the end of a love affair with James Taylor. "It's Too Late" won the Grammy Award for Record of the Year. 07 of 75 Kelly Clarkson - "Since U Been Gone" (2004) Kelly Clarkson - "Since U Been Gone". RCA Arguably, the song "Since U Been Gone" is the one which convinced many pop music observers that Kelly Clarkson had talents as a pop artist that extended far beyond her American Idol victory. Co-writers Max Martin and Dr. Luke stated that they originally intended the song to be recorded by Pink, but she turned it down. Clive Davis convinced them to record the song with Kelly Clarkson, and it became a critically acclaimed multi-platinum pop smash. 06 of 75 Gloria Gaynor - "I Will Survive" (1978) Gloria Gaynor - "I Will Survive". Polydor Gloria Gaynor's disco classic details recovery of personal strength after a bitter breakup. It was a #1 pop hit, and "I Will Survive" has become an enduring anthem of personal empowerment. The recording received a Grammy Award for Best Disco Recording. 05 of 75 Rod Stewart - "Maggie May" (1971) Rod Stewart - "Maggie May". Mercury Rod Stewart's first #1 pop hit deals with a rare situation in breakup songs, the depiction of a young man breaking up with an older woman. The singer says it is more or less true and describes the woman who was the subject of his first sexual relationship. "Maggie May" was initially released as the B-side for "Reason To Believe," but pressure from DJs caused the record to be flipped. 04 of 75 Marvin Gaye - "I Heard It Through the Grapevine" (1968) Marvin Gaye - "I Heard It Through the Grapevine". Motown Songwriter Barrett Strong said the idea for "I Heard It Through the Grapevine" first came when walking down the street in Chicago and he thought about people saying the phrase, "I heard it through the grapevine." The song speaks about hearing of trouble in a relationship indirectly through the "grapevine." Gladys Knight and the Pips released their version of the song in 1967 and it went to #2 on the pop chart. However, it is Marvin Gaye's version from a year later that topped the pop chart for seven weeks and has been hailed as a pop and R&B landmark. 03 of 75 Sinead O'Connor - "Nothing Compares 2 U" (1990) Sinead O'Connor - "Nothing Compares 2 U". Chrysalis Prince wrote "Nothing Compares 2 U" and it was first recorded by his protege group The Family. However, it was Sinead O'Connor's re-recording 5 years later that became a smash hit. Her vocals brought out the emotional pain of the breakup described in the song and it was accompanied by a powerful video in which tears roll down her cheeks. "Nothing Compares 2 U" hit #1 on the pop singles chart and received a Grammy Award nomination for Record of the Year. 02 of 75 Carly Simon - "You're So Vain" (1972) Carly Simon - "You're So Vain". Elektra The lyrics of a few songs have been the subject of as much speculation as "You're So Vain." However, Carly Simon has managed to keep the subject of the song a secret from the general public for 40 years. "You're So Vain" was a #1 pop smash and is considered by many to be the artist's signature song. 01 of 75 Righteous Brothers - "You've Lost That Lovin' Feelin'" (1964) Righteous Brothers - You've Lost That Lovin' Feelin'. Verve This song all about the moment when lovers realize that a relationship is nearing the end is one of the foremost examples of Phil Spector's "Wall of Sound" production technique. Among the background singers is a young Cher. Legendary Brill Building songwriters Barry Mann and Cynthia Weill co-wrote the song with Phil Spector. It was a #1 smash hit single for the Righteous Brothers and a cover of "You've Lost That Lovin' Feelin" helped revitalize the career of Hall and Oates when they took it to #12 in 1980.