Everything That Makes It Worse
Some songs exist specifically to make heartbreak worse. Not accidentally—deliberately, operatically worse—and you seek them out anyway because having a soundtrack to the pain is somehow more bearable than silence. I put together thirty of them.
Sia’s Breathe Me belongs to the category that barely announces itself: just a voice and a slow collapse. Regina Spektor’s Samson works in the same key—a love story told in such specific, strange detail that it feels like reading someone else’s diary and recognizing the handwriting. Fiona Apple’s Never Is a Promise is a controlled demolition in four minutes. Damien Rice’s 9 Crimes is the one you put on when guilt is the specific flavor rather than just sadness—two voices circling each other carefully, not touching. Ingrid Michaelson’s Keep Breathing asks almost nothing of you and still manages to land.
Then there are the ones with enough momentum to keep you moving while they cut. Snow Patrol’s Set the Fire to the Third Bar is technically about distance but lands more like a ghost story. Frou Frou’s The Dumbing Down of Love captures a specific frustration—the moment you realize love made you stupider, and you knew it would, and you let it happen anyway. Bloc Party’s Blue Light ends things with cold grace. Stars’ Your Ex-Lover Is Dead does what the title promises and does it beautifully.
At the theatrical end of the spectrum, where the heartbreak is operatic by design: Evanescence’s My Immortal, which is embarrassing to admit you still find affecting but here we are. Hinder’s Lips of an Angel—a song about calling your ex while your current partner sleeps in the next room, a specific and genuinely terrible situation rendered in the least subtle musical terms possible, and it still works. The Kill by The Dresden Dolls. Paramore’s Franklin, back when they still made music that felt like it might break apart at any moment.
The pop picks, and I’m not apologizing for any of them. Only Hope by Mandy Moore—specifically her version, because the vulnerability in her delivery earns it. Vanessa Carlton’s A Thousand Miles, melodramatic in exactly the right measure. Kate Nash’s Nicest Thing, which is about unrequited feelings and just sits there telling the truth flatly. Nelly Furtado’s Try. JoJo’s Too Little Too Late. The Veronicas’ In Another Life.
The deeper cuts: Jonatha Brooke’s I’ll Try, which deserves far more listeners than it has. Lindsay Lohan’s Confessions of a Broken Heart (Daughter to Father), which is better than the artist’s reputation would suggest and you feel slightly guilty thinking so. Gregory and the Hawk’s Fin Song 8—fragile and small and devastating. Duke Special’s Last Night I Nearly Died. Soko’s I’ll Kill Her, which delivers on its title with a kind of breezy menace. Brett Anderson’s Love Is Dead, from his solo work after Suede.
Two that need no justification: Yesterday by The Beatles, obviously, and Johnny Cash’s Hurt—specifically Cash’s version, the one that sounds like a man taking stock of wreckage he caused himself. The Nine Inch Nails original is harder; Cash’s is truer.
A few German picks that work even if you don’t speak the language: Farin Urlaub’s Phänomenal Egal—he fronts Die Ärzte, Germany’s most beloved punk band, and his solo work is quietly wrecking—Wirtz’s Keine Angst, and Juli’s Wenn du lachst, which hits a frequency of melancholy I find useful regardless of the words.
The antidote—because you need one after all of that—is the Beatsteaks’ Hey Du. Put it on last. It doesn’t fix anything, but it reminds you that you’re still in your body, which is sometimes the whole point.