“Back to Black,” Amy Winehouse

The jazzy swing of “Back to Black” belies the darkness of Winehouse’s challenging mixed emotions. “We only said goodbye with words / I died a hundred times,” she croons. Some failures hurt every time.

“Somebody That I Used to Know,” Gotye

Given a little time and introspection, perhaps the relationship wasn’t so perfect after all. That’s what Gotye and Kimbra are here to tell us on the insidious and light 2011 breakout hit “Somebody That I Used to Know.” “Told myself that you were right for me / But felt so lonely in your company / But that was love and it’s an ache I still remember,” Gotye sings: even the frustrations come with their lingering appeal, despite it all.

“Let Her Go,” Passenger

Passenger has a sweet, light touch on “Let Her Go” that will be soothing to anyone mourning a relationship’s end. “‘Cause you only need the light when it’s burning low / Only miss the sun when it starts to snow / Only know you love her when you let her go,” he sings. Yes: we always want what we can’t have. That bittersweet truth is something we just have to sit with.

“Stay With Me,” Sam Smith

After a breakup, it might not be a bad idea to just play both of Sam Smith‘s albums on back-to-back repeat for a few days — if your heart can handle it. That’s what the British crooner is best at: tapping into that emotional ache and wringing every bit of beautiful sound out of it. When you’re still in the thick of the regret stage, turn to “Stay With Me” to say in song everything you want to say out loud. The melody is so pretty that humming along might help you feel just a little better.

“Irreplaceable,” Beyoncé

“To the left, to the left / everything you own in a box to the left.” In this 2006 classic and breakup mainstay, Beyoncé wrote the playbook on kicking someone out — and when the Queen speaks, it’s worth listening. The gentle R&B ballad is a reminder to value yourself first; let the partners make their own mistakes.

“I Fall Apart,” Post Malone

Post Malone’s big hit may be titled “rockstar,” but it turns out that the bulk of his work is actually not about living the good life. Instead, the Texan singer-songwriter has a knack for setting his heartbreak and emotional vulnerability to music. Exhibit A: “I Fall Apart,” a warbling, raw slow-jam that falls somewhere between ballad and R&B: “Try to brush it off but it keep on goin’ / All these scars can’t help from showing,” he sings, a reminder that self-medication is not always an answer.

“New York,” St. Vincent

Indie darling St. Vincent knows how to hit the emotional pain points on “New York,” her balladic ode to a relationship long gone, and the city that’s changed around her. “New York isn’t New York without you love,” she admits. “I have lost a hero / I have lost a friend / But for you, darling I’d do it all again.” For anyone who’s stayed in place while others have moved on, the soaring, simple tune should hit home.

“Happier,” Ed Sheeran

Turn to Ed Sheeran for that moment when you know your lover has moved on. And it’s a good thing. And yet. “Ain’t nobody hurt you like I hurt you / but ain’t nobody need you like I do,” he reflects on this down-tempo ballad. It’s a moment of resigning yourself to fate, but also accepting that feelings remain.

“Fix You,” Coldplay

Chris Martin kicks things off with a gut punch: “When you try your best, but you don’t succeed / When you get what you want, but not what you need / When you feel so tired but you can’t sleep / Stuck in reverse… When you love someone but it goes to waste / Could it be worse?” Not by much, no. Thankfully we have the soothing chords of Coldplay to wash over us.

“Retrograde,” James Blake

James Blake’s haunting hum of a voice on “Retrograde” and the staticky buzz of the production in the background feels like a hymn. Is it a love song or a song of yearning? Maybe a bit of both, but dark enough to match a heartbreak mood anyway. “We’re alone now,” he intones. “Ignore everybody else, we’re alone now.”