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Haim, Tegan and Sara, Paul Shaffer, more: musicians share their favourite break-up songs

Andrea Warner

Love is great — until it’s not.

Jilter or jilted, break-ups are the worst. It’s like a million ginsu knives to the heart. It’s 1,000 pounds of anxiety and situational depression and sadness sitting on top of your chest. It’s the kind of grief that’s so severe, not even 14 boxes of the softest therapy kittens will make you feel any better (note: the boxes are really small crates that have holes and toys and food, and they’re all adoptable kittens, please don’t worry).

It’s just you and your favourite sad song, maybe you and your ex’s special song, on repeat over and over and over, cocooning deeper and deeper inside your grief with each new play — until one day, maybe, it’s not as bad as it was the day before.

If misery loves company, then, wow, we have the playlist for you. In 2014, a host of great musicians told us about their go-to break-up songs and we’re diving back into this treasure trove of deep cuts and deep feels. Scroll down and read personal stories from Haim, Tegan and Sara, Paul Shaffer and so many more bands and musicians about the songs they turn to for heartbreak and healing.

Joni Mitchell, 'The Last Time I Saw Richard'

"It's the last song on Joni Mitchell’s Blue. I don’t know if it’s a break-up 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 house lights left up bright.' She certainly set the bar high a very long time ago for lyricists." Marissa Nadler

The Be Good Tanyas, 'Broken Telephone'

"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)

Magnetic Fields, 'I Don't Want to Get Over You'

"Last time I was going through a break-up, I sort of obsessively listened to the Magnetic Fields’ ‘I Don’t Want to Get Over You.’" — Sara Quin (Tegan and Sara)

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

"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 had." Chris Carrabba, Twin Forks

Florence and the Machine, 'Dog Days are Over'

"Florence and the Machine’s 'Dog Days are Over' really helped me after my break-up. It was too painful to think about so this song helped me focus on the future and everything I had to look forward to." — Alejandra Ribera

John Lennon, 'Jealous Guy'

"When I was a kid, I loved John Lennon. And I still do. He was my absolute God in terms of finding a way into music. I read so many biographies of him and even when I was way too young to understand the sordid things he was doing in California with Harry Nelson, I understood the drama of that break-up. I really think of 'Jealous Guy,' and that’s not exactly some secret track, but I love that song. And there’s a guy, Donny Hathaway, and he does an amazing live version of it, too. It’s a break-up song, but it’s not defeatist. And maybe that’s because you know the story.... You know that John and Yoko got back together, but it’s a real lamentation." — Doug Paisley

Lou Reed, 'Perfect Day'

"Oh, the break-up and the songs that go with them. In this fog of war we are left raw and bare, usually illuminating our complete inability to be content alone. It can be an embarrassing time. Usually Tom Waits or Morrissey goes on repeat and we get ridiculous haircuts, black clothing and stare out the window for hours believing no one in the world gets our pain. Watching your friend go through a break-up and become a Grade 9-level vampire goth is quite funny. Until you become one during your own time of need. Then it's serious.

"Henry David Thoreau once said, 'Most men (and women) lead lives of quiet desperation and go to the grave with the song still in them.' You don't want to carry this baggage forever. Also, you don't need to embarrass yourself too much in the process. So here is my musical suggestion for awkward times: Lou Reed's 'Perfect Day.'

"It is good for your impending 'goth' phase but is also something to laugh about later, because you will laugh about this later. The glorious strings and refrain 'I'm glad I spent it with you' are perfect for your broken heart, which has been newly cut with a cynical and ironic outlook. As well, 'You're going to reap just what you sow' is nice to mutter on the street as you wish death upon your ex while heading to re-stock your cupboard with Kraft Dinner and ice cream.

"You were whole before you met that person, and you will be whole afterwards. If you weren't, then you have found your real problem. Address that. The truly tragic are those sad people in their later years with pretentious haircuts still chasing tails and still ultimately chasing their own. They are the people of quiet desperation. You are better than that. Love yourself and laugh with yourself my friend; you're all you've got. The sun also rises. It's a perfect day." — Jay Malinowski

Neil Sedaka, 'Breaking Up is Hard to Do'

'Breaking Up Is Hard To Do,' but not the slow way. The fast way, the original way. — Paul Schaffer

Sia, 'Breathe Me'

"I’m not one to mull over break-ups too much, but my go-to song would be Sia's 'Breathe Me.' I love it because it seems to always say how I’m actually feeling. It lets me have one big cry, and then it’s done with. Plus it’s just a gorgeous song." — Nuela Charles

The Avalanches, 'Since I Left You'

"My favourite break-up song is for the breaker uppers. The Avalanches' 'Since I Left You' is the perfect celebratory anthem for unbroken hearts. Lyrically it's very simple and repetitive, which is what's so great about it. The vintage vocal sample simply repeats: 'Since I left you, I found a world so new.' When singing along it becomes a mantra, reassuring you that you're going to be all right. Greater even. The music’s day-dreamy, atmospheric layers are definitely danceable for any (now) solo dance party. It even vaguely sounds like you're at a party so you can fantasize about meeting someone better. Or not." — Lisa Lobsinger (Laser and Broken Social Scene)

Carole King, 'It's Too Late'

"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 that 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)

Tom Petty, 'You Got Lucky'/Toni Braxton, 'Unbreak My Heart'/Joni Mitchell, 'Blue'/Feist, 'Let It Die'

Alana Haim: "You Got Lucky" by Tom Petty is my favourite break-up song. 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.

Este Haim: I think my favourite break-up song is "Unbreak My Heart" by Toni Braxton. I love her.

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

Este: No, I don’t even cry. I love how deep her voice is. [They all break into the opening bars of the song.] I just think of how great her voice is and I think the song is awesome.

Danielle Haim: I’m going to have to go with Joni Mitchell and “Blue.” But also I used to listen to another Canadian artist we really love, Feist, and I remember listening to "Let It Die" in high school.

Alana: Oh, gosh, instant tears.

Hang out with me on Twitter: @_AndreaWarner

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