To celebrate the end of the 2010s, Entertainment Weekly is looking back at the best pop culture of the decade that changed movies, TV, music, and more. Today, we count down the most emotionally devastating songs of the last 10 years.

10. “Self Control” – Frank Ocean

On Blond, Frank Ocean explored the solitude that accompanies longing. Even when falling in love is mutual, it can often remain a solo experience — the fear, the trepidation, the unknowing of it all. “Self Control” is about the nearing end of an affair. “Keep a place for me,” he sings over classic bare guitar strums. “You made me lose my self control.” Instead of feeling betrayed for letting his guard down, Ocean is able to reflect on the gorgeous nostalgia of it all. It’s evoked further with a glorious flourish: a wailing guitar two-and-a-half-minutes into the track that takes the listener above the gloomy clouds to some other time and place in a distant peaceful beyond. —Eve Barlow

9. “Rainbow” – Kacey Musgraves

This ballad off Musgraves’ Grammy-winning Golden Hour began as an encouraging note to herself before morphing into its final version of offering a light for those struggling through hard times. It means so much to Musgraves she even played it at her grandmother’s funeral. The imagery of someone holding tight to their umbrella in a struggle to protect themselves against the elements of life contrasts with the beautiful promise of a rainbow hanging over their head — a symbol of better times ahead. We can’t hear the reminder that it’ll all be alright without sinking into the song’s melancholy melody. Listening to it is like sitting in the storm and chasing the rainbow all in one go. —Maureen Lenker

8. “Writer In the Dark” – Lorde

Ultimately, “Writer In the Dark,” from Lorde’s second coming-of-adulthood LP Melodrama, is a triumphant song about taking the “secret power” back and getting over a toxic ex. But the admission that however claustrophobic the love was, there’ll always be a place for him in her heart is the clincher. Sometimes there’s just no getting over them. And yet the spiked glee that’s wrapped around the lyric “Bet you rue the day you kissed a writer in the dark” is worth the agony and ecstasy of flinging herself wholly and willingly into the destructive arms of heartache in the first place. —EB

7. “Fear” – Kendrick Lamar

To Pimp a Butterfly’s ambition pushed Kendrick Lamar’s already-fervent praise into messianic worship. Its banger-filled follow-up DAMN. switched his focus to the stadiums. But the album’s centerpiece “Fear” focused on Kendrick the human being. The seven-minute essential personally reconnects Lamar to the truth many black people who came up close to poverty and violence carry in their bones: that they can never truly be free. His first two verses are first-person tales of that struggle between the love and fear a child has for one’s elders and a teen’s intimate knowledge of life’s frailty. On its surface, the final verse can read as rich-people paranoia — Rihanna’s accountant purportedly costing her millions is referenced — but its true concern is far less superficial: Even rap’s chosen one is afraid his success story is a dream. —Brian Josephs

6. “Soon You’ll Get Better” – Taylor Swift

This pared-down track that just barely features the Dixie Chicks is a get-well-soon ode to Swift’s mother, Andrea, who is battling cancer again after first being diagnosed in 2015. Swift had previously been relatively tight-lipped on her mother’s illness, but with “Soon You’ll Get Better,” she lets loose. Swift’s pain, worry, and desire to do anything to make her mom heal are palpable in the heartbreaking lyrics, but it’s especially clear in the bridge, which is perhaps the saddest in the singer-songwriter’s repertoire: “What am I supposed to do / If there’s no you?”—Lauren Huff

5. “Your Best American Girl” – Mitski

Mitski is a storyteller, not a memoirist, and her songs should be read that way. “Your Best American Girl” doesn’t gain its power from real-life lyrics (though the struggle of relating to a partner who was raised in a different culture is surely relatable to many listeners) but from the way Mitski’s voice and instrumentals build across different modes, ratcheting from too-cool-for-it deadpan to a devastating crescendo of cathartic ecstasy. That kind of power can defy space and time, which made it such an effective fit to soundtrack a 19th-century sexual awakening on Apple TV’s Dickinson. —Christian Holub

4. “Codeine Crazy” – Future

It’s hard to go wrong in an earnest debate about which project in Future’s Monster-to-Beast Mode-to-56 Nights-to-DS2 run is the best because each one is a legitimate answer. What’s less objective about the hot streak to fans is that its fire was fueled by darkness. The project that kicks it all off ends bleakly with “Codeine Crazy,” where Future delivers his hedonistic deeds not as trophies, but symptoms. “Take all my problems and drink out the bottle and f–k on a model,” he starts his verse, portraying the empty craving of an addict. From that line to the wounded falsetto that close the missive, “Codeine Crazy” narrates submission not hope. —BJ

3. “Praying” – Kesha

In the midst of a legal battle with former collaborator Dr. Luke, Kesha released “Praying,” the lead single off her third studio album, to universal acclaim. While the singer never specifically said the piano pop-ballad was related to the producer, the song, fueled by her demons and suicidal thoughts, became an act of courage and a lesson in forgiveness. In it, a jarring scream at the top of her register shows Kesha reliving the pain of her past before embracing her inner empath. —Ilana Kaplan

2. “Someone Like You” – Adele

Adele’s catalog is designed to draw maximum tears out of its listeners’ eyes, but the 21 track “Someone Like You” is enough of a cry-along ballad to necessitate multiple boxes of tissues. Over a simple piano backing, Adele sings of seeing her ex-lover with someone new and resolving to do better in love next time; her voice remains steely, but crests into desperation as she pleads to not be forgotten. It rolls multiple stages of relationship-ending grief into a single track — and Adele’s selling of it only makes the pain linger more beautifully. —Maura Johnston

1. David Bowie – “Blackstar”

Two days after David Bowe’s Blackstar was released, on Jan. 8, 2015, the cultural icon went gentle into that good night. But not silently. He left a swan song, beautifully, heart-wrenchingly wrought in his final album’s transcendent 10-minute title track, which explores myriad mysterious musical and lyrical ideas. The Starman ascended; did he turn into a “black star” (the opposite of a black hole)? The soaring, spacey, sacred song seems an exploration of his own known mortality. And if Bowie himself is the “solitary candle at the center of it all,” now devastatingly extinguished, his glittering stardust lives on inside us all. —Katherine Turman