Linda Ronstadt – Long, Long Time
When Linda Ronstadt belts those high notes in the last verse, knees buckle and the flood begins. Couldn’t listen to it for a long, long time after a particularly brutal betrayal. Crushing … BarerBear
Alanis Morrissette – You Oughta Know
The fury of it spoke volumes when I was dealing with a painful breakup from someone who cheated on me, broke my heart, but wanted to stay friends. morgarf
The Waterboys – Rags
It’s not subtle and it sure isn’t a “slowie”. Mike Scott chucks everything in here musically and lyrically, including religious imagery, but, wow, it still packs a punch 40 years after a 17-year-old heartbroken me used to wallow in all its self-loathing glory! Mozzah
Boz Scaggs – It’s Over
There are the slow “I’m not really over you” bits, but most of it is a driving blues that says, “get out.” Being able to articulate the fed-up-to-the-teeth parts of a breakup is important. fabrisse
Tom Waits – Martha
Still the saddest, most beautiful song I know. And it’s always blown my mind he was only 23/24 when he wrote it – clearly demonstrating a wisdom way beyond his years. A masterpiece for me. JohnAldridgesUSARant
Cinerama – Careless
Staying friends, or at least some semblance of a friendship, after a breakup – but it still manages to convey that post-breakup package of emotions – resentment, wistfulness for what is lost, etc. Extra points for the song apparently involving a band member who is in the background of most of the video. Marsilio1
Elbow – The Bones of You
Garvey is a fine lyricist but cuts your heart out with the closing line as he’s walking down the road and hears an old song from a long-forgotten love – “And the sickener hits / I can work till I break / But I love the bones of you / That I will never escape.” Kills me every single time. VAgent
Marlon Williams – Nobody Gets What They Want Anymore
It’s so beautifully desolate, honest and sad and there’s no resolution at the end. I’ve heard so many songs with men singing, “What am I going to do without you?” but hearing, for once, “What are you going to do without me?” really hits me hard. fixitgirl
Bonnie Raitt – I Can’t Make You Love Me
It’s had at least three major recordings by different artists, but something I’ve noticed is that people who have a favorite don’t usually denigrate the other performances – they just think they aren’t quite as achingly perfect as their own favorite. For myself, it’s gotta be Bonnie Raitt, with Bruce Hornsby on piano. This is the breakup song for grownups. It doesn’t indulge in a toddler-ish need to hate the other person; it’s just filled with love and sorrow and resignation. LouisRiel
Black Sabbath – Changes
Ozzy sounded as though his heart had been ripped into a million pieces. Clareontarget
Kele – All the Things I Could Never Say
This song helped me end a bad relationship, and, seven years later, still makes me feel every hard, devastating emotion. DressedInDreams
Son House – Special Rider Blues
An amazingly powerful piece of music of Son at or near his peak that shows what Delta blues might really have sounded like played in the back streets of Mississippi. The last 30 seconds of slide guitar is incredible. StrangeBrew
Benji Lewis – Never Mine
… completely mirrored my feelings as I went through a breakup with someone I completely adored. Playing it helped heal me but also amplified the hurt – but at least it sounded like someone else was going through dark days. Beautiful breakup song. andromc
The Who – So Sad About Us
What’s great about it is that the lyrics are just straight, literal breakup lyrics (“sad, never meant to break up / Sad, suppose we’ll never make up”), no story, no evocative details, no frills, just “this is a breakup song.” And at the same time the music is gloriously uplifting, positively exulting, especially that harmony on the chorus. It’s almost like the lyrics are ironic and person is actually happy, free and in love with life. cerealcat
Elvis Costello & the Attractions – I Want You
The sheer visceral loss verging on the psychotic that Costello imparts is, especially on a first listen, quite breathtaking. dnky666
The Cinematic Orchestra – To Build a Home
It came out not long before I split from my ex-partner in 2007, and although I’ve happily been with the love of my life since 2008, hearing that song transports me straight back to the tears and heartache I felt at the time. 231184
Harry Nilsson – Without You
You could bet every time it was played at a disco or a party in the early 70s there’d be someone crying in a corner. bean55
The Cruel Sea – The Honeymoon Is Over
It has everything you need in a breakup song. Hurt, indignation, anger, vengeance, pettiness but, most of all, an overwhelming sense of finality. All this is carried by driving moody music and unrelenting powerful vocals. If I ever found myself on either side of a breakup I reckon I would lock myself in a room and listen to this for a week. PablitoMcPollo
The Dells – The Love We Had (Stays on My Mind)
A magnificent 70s soul recording that reveals a lover unable to forget the love he once had. A beautiful lyric made into something even more special by the incredible vocals, from piercing falsetto to a roaring, growling tenor baring his soul for all to hear. The live version is fabulous too. telboy1959
Leonard Cohen – So Long Marianne
Heartbreak without self-pity, no raging at your ex. In a nutshell: “Yes, this is awful, but this is what life gives you, so we’ve just got to live with it.” tiofrancisco
