1. Freda Payne, “Band of Gold”
The greatest Motown song that never was. A dark track about a couple’s marriage falling apart on their wedding night because he is incapable of loving her.
Quintessential breakup lyrics: “All that’s left of the dream I hold is a band of gold / And the dream of what love could be.”
2. Bill Withers, “Ain’t No Sunshine (When She’s Gone)”
Bill Withers told Song Facts that the inspiration for the song wasn’t a personal relationship, but rather the 1962 movie Days of Wine and Rose.
Quintessential breakup lyrics: “Only darkness every day / Ain’t no sunshine when she’s gone / And this house just ain’t no home.”
3. Linda Ronstadt, “You’re No Good”
Written by Clint Ballard Jr., the song was originally recorded by Betty Everett in 1963 and reached No. 51 on the Billboard Hot 100 — but it was Linda’s powerful 1975 version that catapulted this song to No. 1.
Quintessential breakup lyrics: “Feeling better ‘cause I’m over you / I learned my lesson, it left a scar.”
4. Rod Stewart, “Maggie May”
A tale of a May-December relationship gone horribly wrong.
Quintessential breakup lyrics: “You led me away from home just to save you from being alone / You stole my heart, and that’s what really hurts.”
5. Derek and the Dominos, “Bell Bottom Blues”
The emotional anguish in Eric Clapton’s voice perfectly captures the pain of trying to keep a relationship alive.
Quintessential breakup lyrics: “Give me one more day, please / I don’t want to fade away / In your heart, I long to stay.”
6. Chicago, “If You Leave Me Now”
Lyrics that anyone who has ended a long-term relationship can relate to.
Quintessential breakup lyrics: “A love like ours is love that’s hard to find / How could we let it slip away / We’ve come too far to leave it all behind / How could we end it all this way?”
7. Joni Mitchell, “River”
Following a difficult breakup with musician Graham Nash, Joni penned the essential breakup album Blue, and while any track from that album could work on this list, “River” beautifully captures the emotion of reflecting on a past relationship during the holidays.
Quintessential breakup lyric: “I made my baby say good-bye.”
8. Bob Dylan, “If You See Her, Say Hello”
Easily the most heartbreaking track from Bob Dylan’s essential breakup album Blood on the Tracks, “If You See Her, Say Hello” is about being happy for your ex for moving on, even when you are still deeply wounded inside.
Quintessential breakup lyrics: “If you get close to her, kiss her once for me /
I always have respected her for busting out and gettin’ free / Oh, whatever makes her happy, I won’t stand in the way.”
9. Ann Peebles, “I Can’t Stand the Rain”
Sometimes it’s the little things that will trigger memories about a person long after the relationship has come to an end.
Quintessential breakup lyrics: “Alone with the pillow / Where his head used to lay / I know you’ve got some sweet memories.”
10. The Carpenters, “Superstar”
The Carpenters’ version of “Superstar” peaked on at No. 2 on the Billboard Hot 100 (it was unable to claim the top spot due to the success of Rod Stewart’s “Maggie May”) and is considered one of their signature songs. Reportedly, Karen Carpenter did her beautifully haunting vocals all on the first take.
Quintessential breakup lyrics: “Loneliness is such a sad affair / And I can hardly wait to be with you again / What to say to make you come again?”
11. Daryl Hall & John Oates, “She’s Gone”
The perfect song about having a breakup slowly begin to sink in.
Quintessential breakup lyrics: “She’s gone / I better learn how to face it.”
12. Carly Simon, “You’re So Vain”
“You’re So Vain” is arguably the best revenge song ever written.
Quintessential breakup lyric: “But you gave away the things you loved and one of them was me.”
13. Elton John, “Sorry Seems to Be the Hardest Word”
A haunting ballad about a relationship falling apart.
Quintessential breakup lyrics: “What do I say when it’s all over / Sorry seems to be the hardest word.”
14. Dolly Parton, “We Used To”
Dolly’s lyrics and heart-wrenching delivery capture the pain of reminiscing on happier times. And yes, she pretty much lifted the entire guitar intro from Led Zeppelin’s “Stairway to Heaven.”
Quintessential breakup lyrics: “And even though you’re gone / I still think so often of you / And the things that we no longer do.”
15. The Rolling Stones, “Angie”
Despite wide-ranging rumors about what/who “Angie” was written about, one thing is clear: This was a relationship that was never meant to be.
Quintessential breakup lyrics: “All the dreams we held so close seemed to all go up in smoke.”
16. Carole King, “It’s Too Late”
“It’s Too Late” perfectly sums up the point when you know the relationship has run its course.
Quintessential breakup lyrics: “It’s too late baby / Now it’s too late / Though we really did try to make it.”
17. Fleetwood Mac, “Go Your Own Way”
Lindsey Buckingham took some nasty parting shots at Stevie Nicks on “Go Your Own Way,” which was the first single released off the ultimate breakup album Rumours.
Quintessential breakup lyric: “Loving you isn’t the right thing to do.”
18. Fleetwood Mac, “Silver Springs”
Written by Stevie Nicks after her breakup with Lindsey Buckingham, “Silver Springs” (originally intended for the album Rumours) is a slow burn of a song, about the difficulty in trying to forget someone you loved so deeply.
Quintessential breakup lyrics: “Time cast a spell on you, but you won’t forget me / I know I could have loved you, but you would not let me.”