Music

Haim, Paul Shaffer and more musicians share their favourite breakup songs

A Valentine's playlist for everybody else.

A Valentine's playlist for everybody else

Roses are red, violets are blue, famous musicians get their hearts broken, too. (Getty Images (JHaim by Jason Merritt; Paul Shaffer by Jamie McCarthy))

The original version of this piece was published by CBC Music in 2014. 

Love is great — until it's not. 

Jilter or jilted, breakups are the worst. It's just you and your favourite sad song — maybe you and your ex's special song! — on repeat over and over and over again. Cue Aimee Mann's "One is the Loneliest Number." 

But, misery loves company, and boy, do we have the playlist for you. In 2014, a number of great musicians told us about their go-to breakup songs and we're diving back into this treasure trove of deep cuts and deep feels. Scroll down and read Haim, Paul Shaffer, Brendan Canning and more musicians' picks for the songs that help them deal with heartbreak.


'The Last Time I Saw Richard,' Joni Mitchell 

"I don't know if it's a breakup song or not, but it certainly deals with moving apart from someone in both a physical and emotional sense. We all move on from people, and some fare better than others. The lyrics are incredible: 'Richard got married to a figure skater/ and he bought her a dishwasher and a coffee percolator/ and he drinks at home now most nights with the TV on/ and all the houselights left up bright.' She certainly set the bar high a very long time ago for lyricists." Marissa Nadler, singer-songwriter



'Broken Telephone,' the Be Good Tanyas 

"The first time I really had my heart broken I used to listen to that song all the time. It's a really great song. They're a three-piece and they sing in three-part harmony, kind of alt-country. There's this line, and I'm going to f--k it up, but God, the person who broke up with me, when she broke up with me she was like, 'You tried to change me and I'm good the way I am!' I totally did not try to change her, but I just was so tragic and young that I really bought it. There was this line in the song basically saying, 'I tried to change you and there's nothing wrong with you' and I would just lay in bed and be like [singing loudly] 'There's nothing wrong with you!' [Laughs]" Tegan Quin, Tegan and Sara


'You're Gonna Make me Lonesome When You Go,' Bob Dylan 

"This song is so powerful even though language is so casual. The heartbreak in it is palpable but the lyrics are constructed with so many layers that at first you get the feeling that he doesn't care too deeply about the loss. With every listen the intensity of the loss deepens until the pain is real to the listener. Then a curious thing happens. After more and more plays of the song, the listener returns to the less painful and almost playful version they had heard the first time. The song seems to mirror the stages of heartbreak in that way. At first there is almost the feeling of lightness that comes from the weight of the relationship being removed, which leads to the unbearable weight of the pain ... but ultimately the experience as it was becomes more important to them than the pain of the ending, and from there on the lightness returns to their view of what they had." Chris Carrabba, Dashboard Confessional


'Nothing More to Say,' Joel Plaskett Emergency 

"You've just broken up with the love of your life, who also turns out to be a soulless fraud, and you're driving aimlessly in the rain with a tear-stained face. You're bursting inside but you have no more tears. So you crank up the stereo and belt out the words, 'Don't call me up when you figure it out, I've got nothing more to say to you!' and pound your fists against the steering wheel along with the triumphant guitar riff.  You swear on the censor and call out 'Pretender!' It's so satisfying that you do it 10 times, 'til you're sleepy and hungry and forget about being sad for a while." Colleen Brown, singer-songwriter


'Breaking up is Hard to Do,' Neil Sedaka 

"But not the slow way. The fast way, the original way." Paul Shaffer, musician and bandleader


'It's Too Late,' Carole King 

"Lyrically, Carole really nails the vibe superbly. You know, it feels like I'm in the room with this couple she's singing about. The solo breaks are absolutely gorgeous and the playing throughout the track is, of course, dead on. Bass playing, please. The fact she sings, 'Though we really did try to make it' is such a hopeful and positive line and a great reflection on what was once a beautiful relationship but has now changed and there's no hiding it. It's a wonderful sentiment for the human race. And musically, it's a banger.  From the arrangement to every single component, a knockout from top to bottom. 'Tis the work of pure heavyweights." Brendan Canning, Broken Social Scene


'You Got Lucky,' Tom Petty 

"It's more like an 'eff you' song. When I get broken up with — like, I've never broken up with anyone, I've never had the chance to be that person — but whenever I would get broken up with, because it's happened many times [laughs], I always put on that song and it whips me back into shape and you just kind of continue on. It's saying, 'You got lucky when I found you' and it's like, boo-yah! On with my day, straightened out." Alana Haim, Haim


'Blue,' Joni Mitchell and 'Let It Die,' Feist 

Danielle Haim: I'm going to have to go with Joni Mitchell and "Blue." Another Canadian artist we really love is Feist and I remember listening to "Let it Die" in high school.

Alana Haim: Oh, gosh, instant tears.


'Unbreak my Heart,' Toni Braxton

Este Haim: I think my favourite breakup song is "Unbreak my Heart" by Toni Braxton. I love her.

Alana Haim: That's a good one. I would just cry.

Este: No, I don't even cry. I love how deep her voice is. [All three Haim sisters break into the opening bars of the song.] I just think of how great her voice is and I think the song is awesome.

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