In the wake of a heartbreak, many of us turn to music.
Songwriters have been writing about breakups — more specifically the romantic kind — for decades. There is, after all, a lot of varying emotions felt as one’s heart gets broken, depending on the circumstances: sadness, anger, relief, frustration, jealousy, contempt, loneliness and plenty more in between, sometimes all felt in the same day. (There is also the platonic kind of heartbreak: band breakups, rifts between siblings, broken creative partnerships, etc.)
Often, writing the song is just as cathartic an experience for the artist as it is for a listener to hear it, and there’s something comforting in knowing that heartbreak happens to the best of us. Channeling those feelings into writing or singing along can help tremendously. As Phil Collins put it in his memoir: “People hate a breakup, but they love a breakup song.”
READ MORE: 22 Scathing Rock Star Breakup Quotes
Maybe you’ve just parted ways with someone you thought was meant to stick around forever. For that we might suggest a song like Bob Dylan‘s “Don’t Think Twice, It’s All Right.” Or perhaps you’ve recently learned of a betrayal of some sort and need a tune to sing at the top of your lungs — try Linda Ronstadt‘s “You’re No Good.” There’s also the possibility that you’ve already done some healing and are ready for a new chapter of life. For that, the Byrds‘ “I’ll Feel a Whole Lot Better” is appropriate.
These songs and many more can be found below.
40. “Don’t Go Away Mad (Just Go Away,)” Motley Crue
From: Dr. Feelgood (1989)
Bassist Nikki Sixx has said that he got the title line for “Don’t Go Away Mad (Just Go Away),” the fourth single from Dr. Feelgood, from a movie, though he could not recall which one. (Further research has revealed he likely meant 1986’s Heartbreak Ridge.)
39. “If You Leave Me Now,” Chicago
From: Chicago X (1976)
Written and sung by bassist Peter Cetera, “If You Leave Me Now” was Chicago’s very first No. 1 hit, topping the charts for two weeks. As if that wasn’t impressive enough, it also earned them two Grammys: Best Arrangement Accompanying Vocalist(s) and Best Pop Vocal Performance by a Duo, Group or Chorus.
38. “Black,” Pearl Jam
From: Ten (1991)
“It’s about first relationships. The song is about letting go,” Eddie Vedder explained of “Black” in the 2011 book Pearl Jam Twenty. “It’s very rare for a relationship to withstand the Earth’s gravitational pull and where it’s going to take people and how they’re going to grow. I’ve heard it said that you can’t really have a true love unless it was a love unrequited. It’s a harsh one, because then your truest one is the one you can’t have forever.”
37. “Piece of My Heart,” Big Brother and the Holding Company
From: Cheap Thrills (1968)
The first artist to record “Piece of My Heart” was Aretha Franklin‘s older sister, Erma, who released the original version of the song in 1967. A year later, Janis Joplin put her now-iconic touch on it with Big Brother and the Holding Company, turning it into a rumbustious No. 12 hit.
36. “Idiot Wind,” Bob Dylan
From: Blood on the Tracks (1975)
Breakups are hard enough without your former partner calling you an idiot, but leave it to Bob Dylan to really twist the knife with a nearly eight-minute song about exactly that. Sinead O’Connor put it best to Entertainment Weekly in 2001: “Bob gave me permission to be angry because of his song ‘Idiot Wind.’ None of us would like to be the person he’s talking to [in that]. That’s why I love Bob Dylan. He’s utterly honest. He can be real f—ing nasty.”
35. “September Gurls,” Big Star
From: Radio City (1974)
Love triangles happen to the best of us, including Alex Chilton of Big Star. “September Gurls” was written about three different women in Chilton’s life at the time, his ex-wife among them, all of whom happened to have September birthdays. “December boys got it bad,” Chilton sings, a clear reference to himself and his own birth month.
34. “I Can’t Make You Love Me,” Bonnie Raitt
From: Luck of the Draw (1991)
There were three artists considered for the first recording of “I Can’t Make You Love Me,” written by the highly successful team of Mike Reid and Allen Shamblin: Bonnie Raitt, Bette Midler or Linda Ronstadt. In the end, it was given to Raitt, who recorded the vocal in a single take — nothing topped the emotion of the first one. “We’d try to do it again,” Raitt recalled in 2002, “and I just said, ‘You know, this ain’t going to happen.'”
33. “Walking on Broken Glass,” Annie Lennox
From: Diva (1992)
“The alternative title for ‘Broken Glass’ could easily have been ‘Hell hath no more fury than a woman scorned,'” Annie Lennox wrote in a 2009 blog post (via Songfacts). The lyrics imply more anguish than anger, but watch the accompanying music video and you’ll see Lennox stare daggers at her former lover, played by John Malkovich.
32. “Maggie May,” Rod Stewart
From: Every Picture Tells a Story (1971)
According to Rod Stewart himself, “Maggie May” is based on the true story of how he lost his innocence to an older woman at the 1961 Beaulieu Jazz Festival, years before he wrote the song. “She dragged me into her tent, and this was the middle of the afternoon, and the deed was done,” he explained to 60 Minutes Australia in 2019. Whatever happened to that specific woman is unclear, and the song became more generally about an older partner who has taken advantage of Stewart’s love.
31. “Always on My Mind,” Elvis Presley
From: Separate Ways (1972)
Many have covered “Always on My Mind,” including but not limited to: Brenda Lee, Willie Nelson, Pet Shop Boys and more. But it’s Elvis Presley’s 1972 version that really drives home the message, which he recorded shortly after separating from his wife, Priscilla. The only thing harder than a heartbreak is looking back and realizing what you could have done differently.
30. “I Heard It Through the Grapevine,” Marvin Gaye
From: In the Groove (1968)
Some people spend months debating whether to end a relationship, but not the narrator of “I Heard It Through the Grapevine,” who wastes no time calling things off when they find their lover to be unfaithful. It was first recorded by Gladys Knight & the Pips in 1967, and again by Creedence Clearwater Revival in 1970, but Marvin Gaye’s 1968 version is the definitive one.
29. “What It Takes,” Aerosmith
From: Pump (1989)
The first line of Aerosmith’s “What It Takes” sets the scene immediately: “there goes my old girlfriend.” But the band was bound and determined not to make the song sound too much like a country-western, woe-is-me type track, even if that was the direction co-writer Desmond Child usually went for. Striking that balance ended up earning the band a Top 10 hit.
28. “Silver Springs,” Fleetwood Mac
From: 1976 B-Side Single
Fleetwood Mac is no stranger to the breakup song, but that’s bound to happen when you’ve got songwriters in the same band pursuing relationships with one another. Arguably one of the most stunning is Stevie Nicks‘ “Silver Springs,” a song she has never shied away from saying is about her breakup with Lindsey Buckingham. “I know I could’ve loved you,” Nicks insists, “but you would not let me.”
27. “Backstreets,” Bruce Springsteen
From: Born to Run (1975)
Whoever Terry is, the main subject of Bruce Springsteen’s song “Backstreets,” they really did a number on him emotionally. One might assume this is about a former girlfriend or some kind of romantic love interest, but as far as Springsteen sees it, it’s more general than that. “Just youth, the beach, the night, friendships, the feeling of being an outcast and kind of living far away from things in this little outpost in New Jersey,” he said to Rolling Stone in 2016. “It’s also about a place of personal refuge. It wasn’t a specific relationship or anything that brought the song into being.”
26. “You’re Breakin’ My Heart,” Harry Nilsson
From: Son of Schmilsson (1972)
The reality of heartbreak is that it can bring out some really hurtful words. This is illustrated clearly in Harry Nilsson’s “You’re Breakin’ My Heart.” “You’re tearing it apart so f— you,” he sings, also accusing his ex of breaking his glasses. Thanks to the songs’ curse words, it was not released as a single as Nilsson had originally wanted.
25. “Against All Odds (Take a Look at Me Now),” Phil Collins
From: 1984 Singles
Sometimes marriage is forever, sometimes it’s not. It wasn’t for Phil Collins, who found some inspiration for new music when he split from his first wife in 1980 and began to move on. When asked to write a song for the 1984 film Against All Odds, Collins’ was through with one divorce — at present, he has been divorced three times — and about a year away from marrying again. “There’s nothin’ left here to remind me / Just the memory of your face.”
24. “Baby Come Back,” Player
From: Player (1977)
In times of turmoil and sadness, it’s good to lean on friends. Such was the case when two members of Player, Peter Beckett and J. C. Crowley, were both going through breakups at the same time. Together they penned 1977’s “Baby Come Back,” one of rock’s most desperate pleas for the return of a lover.
23. “You Oughta Know,” Alanis Morissette
From: Jagged Little Pill (1995)
Alanis Morissette has never publicly stated who the song “You Oughta Know” is about. Frankly though, the real power in the song isn’t in the subject’s identity, but in the searing words she uses. “Every time you speak her name,” she sings, directing her aim at the new girl in the picture, “Does she know how you told me you’d hold me until you died?“
22. “I’ll Feel a Whole Lot Better,” The Byrds
From: Mr. Tambourine Man (1965)
When Gene Clark of the Byrds sings about running away from his relationship “after what you did” in 1965’s “I’ll Feel a Whole Lot Better,” he does not elaborate on what happened. The lyrics don’t really get too specific, but one thing is abundantly clear: “I’ll probably feel a whole lot better when you’re gone.”
21. “Train in Vain,” The Clash
From: London Calling (1979)
“The track was like a train rhythm, and there was, once again, that feeling of being lost,” Mick Jones of the Clash explained of the song “Train in Vain” to Blender in 2002, which may have had something to do with his split from guitarist Viv Albertine of the Slits. “You didn’t stand by me, no, not at all,” he insists, handling lead vocals instead of Joe Strummer.
20. “Pictures of You,” The Cure
From: Disintegration (1989)
Is there anything more heartbreaking than looking back at old photos from a relationship you thought would last forever? “I’ve been looking so long at these pictures of you,” Robert Smith sings, “that I almost believe that they’re real.” Smith himself has been married to his wife Mary Poole, whom he met at the age of 14, since 1988. Still, he knows how hard it can be to look back at what once was.
19. “Yesterday,” The Beatles
From: Help! (1965)
As one of the most covered songs in all of music history, Paul McCartney‘s “Yesterday” has become something of a pop standard. It is perhaps the best encapsulation of how quickly heartbreak can happen. One moment love appears an easy game to play, full of promise and excitement, the next it seems to have vanished, leaving only despair and hopelessness in its wake.
18. “Tangled Up in Blue,” Bob Dylan
From: Tangled Up in Blue (1975)
If you thought there was only room for one Tangled Up in Blue song on this list, think again. The title track to Dylan’s 1975 album is much less biting than “Idiot Wind,” and instead highlights how two people can love each other dearly and still not see eye to eye — “We always did feel the same / We just saw it from a different point of view.”
17. “Love Will Tear Us Apart,” Joy Division
From: 1980 Single
Ian Curtis of Joy Division married Deborah Woodruff in 1975, the same year Captain & Tennille had a hit with “Love Will Keep Us Together.” Five years later, Curtis argued the opposite, “Love Will Tear Us Apart.” The reality, he emphasized in the lyrics, is that people in relationships are not constant: “We’re changing our ways / Taking different roads.”
16. “You’re No Good,” Linda Ronstadt
From: Heart Like a Wheel (1974)
Enough with the self-pity for a moment, here’s something more upbeat: Linda Ronstadt’s “You’re No Good.” As its title suggests, there is no doubt that the singer has moved on from her former beau, and is in fact taking the time to point out that she’s learned her lesson being with someone below her standards. (She also, it must be said, notes that she would understand if someone said the same about her.)
15. “River,” Joni Mitchell
From: Blue (1971)
Not every breakup has a hero and a villain, and often there is accountability to be had on both sides. Joni Mitchell knew this, as she implicated herself in the dissolution of her relationship (presumably with Graham Nash) in the song “River.” “I’m so hard to handle / I’m selfish and I’m sad,” she admits. “Now I’ve gone and lost the best baby that I ever had.”
14. “For No One,” The Beatles
From: Revolver (1966)
“I suspect it was about another argument,” Paul McCartney once said of “For No One.” At that time in 1966, he was in a relationship with Jane Asher, one that had started in 1963 and would ultimately end in 1968. Clearly not everything was perfect for the couple in those five years, as this song indicates.
13. “Crying,” Roy Orbison
From: Crying (1962)
When Roy Orbison’s co-writer came up with the line “once again I’m crying,” it all came flooding back. “Immediately I thought of a past experience and just retold that, was the way that came about,” he told NME in 1980 (via Songfacts). “It was the retelling of a thing with a girlfriend that I had had. I couldn’t tell you right now what notes I hit at the end of the song, or anything.”
12. “Don’t Think Twice, It’s All Right,” Bob Dylan
From: The Freewheelin’ Bob Dylan (1963)
Like others on this list, Dylan has long refrained from outwardly naming the subject of his songs. If we consider the context though in which “Don’t Think Twice, It’s All Right” was written, it would not be unreasonable to think Dylan wrote it about his former girlfriend Suze Rotolo, who at that time was traveling abroad in Italy with no real plans to return to Dylan in NYC. His send-off is both calm and acute: “You could’ve done better but I don’t mind / You just kinda wasted my precious time / But don’t think twice, it’s all right.”
11. “Babe I’m Gonna Leave You,” Led Zeppelin
From: Led Zeppelin (1969)
Written by Anne Bredon, “Babe I’m Gonna Leave You” began its life as a folk number in the ’50s. In 1962, the first published version of it appeared on Joan Baez‘s 1962 album Joan Baez in Concert. Seven years later, Led Zeppelin put their own hard rock spin on it, with Robert Plant‘s wailing vocal really driving home the message.
10. “Without You,” Harry Nilsson
From: Nilsson Schmilsson (1971)
Here is the other side of Harry Nilsson, not the angry one from “You’re Breakin’ My Heart” — though to be fair, anger is often a perfectly valid emotion during a heartbreak. Here Nilsson is much more tender: “I can’t live if living is without you.” We would also recommend the versions of this song recorded by Badfinger (1970) and Mariah Carey (1994).
9. “Drive,” The Cars
From: Heartbeat City (1984)
The thing about the Cars’ “Drive” is that it could be interpreted two ways. “Who’s gonna tell you when it’s too late? / Who’s gonna tell you things aren’t so great?” Is the narrator directing those questions at their partner? Or are they asking those questions of themselves?
8. “She’s Gone,” Hall and Oates
From: Abandoned Luncheonette (1973)
Both Daryl Hall and John Oates were purportedly going through romantic issues at the time they sat down to write “She’s Gone,” so there’s double the heartbreak. Interestingly, the song only went to No. 60 on the Billboard Hot 100 when it first came out as a single in 1973, but when it was re-released in 1976 it jumped to No. 7.
7. “I Will Always Love You,” Dolly Parton
From: Jolene (1974)
Dolly Parton actually wrote “I Will Always Love You” as a tribute to her entirely platonic business partner and mentor Porter Wagoner when she decided to embark on a solo career. Still, the song can apply to romantic heartbreak, or really any other kind of relationship loss based on mutual respect and admiration for the other.
6. “It’s Too Late,” Carole King
From: Tapestry (1971)
Sometimes there comes a point of no return, even when no one is at fault, as Carole King describes in “It’s Too Late.” King herself did not write the lyrics, but she could feel them, having gotten a divorce from Gerry Goffin just three years prior to recording the song.
5. “Ain’t No Sunshine,” Bill Withers
From: Just As I Am (1971)
Bill Withers may have put it best: splitting from a loved one can truly feel like the sun has stopping shining. Withers was inspired by characters in the 1962 movie Days of Wine and Roses, starring Lee Remick and Jack Lemmon. “They were both alcoholics who were alternately weak and strong,” he once explained to Songfacts. “It’s like going back for seconds on rat poison. Sometimes you miss things that weren’t particularly good for you. It’s just something that crossed my mind from watching that movie, and probably something else that happened in my life that I’m not aware of.”
4. “Angie,” The Rolling Stones
From: Goats Head Soup (1973)
If anything, the subject of “Angie” is probably a conglomerate of several people in the lives of Keith Richards and Mick Jagger. Regardless, it’s an excellent example of the Stones’ talent for writing blues rock ballads, complete with Jagger’s slightly southern-sounding twang. And don’t overlook Nicky Hopkins‘ subtle yet essential piano part.
3. “You’re So Vain,” Carly Simon
From: No Secrets (1972)
Not to invoke the cliche but sometimes it’s just true: hell hath no fury like a woman scorned. Carly Simon wanted to make sure that even if she never explicitly stated his identity, the egotistical and sharp-dressed subject of 1972’s “You’re So Vain” was enshrined in song forever.
2. “Nothing Compares 2 U,” Sinead O’Connor
From: I Do Not Want What I Haven’t Got (1990)
Prince may have written “Nothing Compares 2 U,” but it was Sinead O’Connor who brought the sorrow and turned it into one of the most gut-wrenching breakup tracks of all time. “It’s really about emotions, it’s not about notes,” O’Connor told BBC 6 Music in 2016.”I think I’m probably similar to millions of people who loved the song, and we’re all people who associated the song with a loss of some kind.”
1. “Go Your Own Way,” Fleetwood Mac
From: Rumours (1977)
Lindsey Buckingham, also known as Stevie Nicks‘ ex-boyfriend, really wasn’t planning on writing the kind of blistering breakup song that “Go Your Own Way” became. “There was nothing about it that was thought out,” he said in a 2018 episode of Song Exploder. “It was just the raw expression of the emotion behind the song.”
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