“Romeo & Juliet” by Dire Straits
As much as nobody likes admitting it immediately before, during or after a breakup, some relationships are doomed from the start. That doesn’t mean fate has anything to do with it; it’s more likely a combination of incompatible beliefs, bad hygiene, a lack of conversational prowess or something in the bedroom (that should or shouldn’t have been done regularly) dealing those final blows to what seemed initially like love ever after. Let’s face it, Romeo and Juliet had it harder than we ever do. If you’re breaking up — and it’s definitely going to be rough — listen to Mark Knopfler’s more modern take on those star-crossed lovers. It’s an expert musical reminder that the end always seems so grand and heartrending and tragic, even if both parties kind of knew it was coming. Romeo says it best: “When you gonna realize it was just that the time was wrong, Juliet.” - Michael Merline
“Title and Registration” by Death Cab for Cutie
This one goes out to the summer of 2006. Sparing the details, there was a boy, a girl, and a distance just the wrong side of right. It didn’t work out, and as happens with the jilted, there was music to be absorbed.
Death Cab for Cutie’s Transatlanticism was an album I always enjoyed, but its themes of distance and longing were meaningless to me until ’06. One particular day, while freshly draped in heartbreak, I [CLICHE ALERT] listened to every word of “Title and Registration.” What I previously thought was a clever song about comparing old memories to being pulled over had a thorough resonance. Gibbard’s conviction, especially when he bleeds out “Where disappointment and regret/ Collide/ Lying awake at night” really made me understand that while I was alone, I wasn’t alone with this feeling.
Through the spring and into the summer and the inevitable fall, Gibbard’s words were my own, and suddenly staring out the car window wasn’t what it used to be. The world wasn’t passing by anymore. It was leading the way to better days. – Rafael Gaitan
“Can’t Fight It” by Bob Mould
If you were my best friend in high school who lent me my first Cure tape (The Head on the Door), let me read your Sandman comics even though you were nervous I would handle them improperly and called me during “Twin Peaks” so we could watch together, silently, over the phone, you know this song well. Bob Mould’s sad/lovely single “Can’t Fight It” from ‘90s compilation par excellence No Alternative is not only one of the finest songs in Mould’s comprehensive discography, but the very same that I dubbed over some crappy cassingle and sent you in the mail that summer. Mould smoothes out his gravel by singing with a sense of loving defeatedness and laying orchestral melody into the final instrumental phrases. This is a song of admittance and acceptance. “I can never hold you down again/ This I understand… It’s gone and I can’t fight it/ You’ve gone and I can’t fight it”: that’s the part that killed me but also made me realize you were right. Sometimes the worst breakups are the ones that never involved romance in the first place. – Stacey Pavlick
“Breakin’ Up” by Rilo Kiley
At first, I pored over my iPod for the most anguished, tortured, seriously sad breakup song to share with you, but then I realized that nobody wants to be single and sad around Valentine’s Day. Plus, sometimes your special someone really sucks and breaking up is a relief. The obvious choice was then Rilo Kiley’s “Breakin’ Up.” Ever wry, Jenny Lewis asks her ex if she’s feigned agony long enough and can get back to a world that goes on without him. On an album with some of the band’s best and worst songs, “Breakin’ Up” is a highlight – a gospel choir, Jason Boesel’s epic dance beat and a triumphant, uplifting, fuck-you chorus: “Ooh, it feels good to be free!” – Katie Bolton
“Landlocked Blues” by Bright Eyes
“Landlocked Blues” is about feeling restless and leaving things behind. It’s the perfect song for that post-breakup stage in which the future seems uncertain. It’s not about that kind of emotionally violent, slam-the-door, scream-curses-at-your-partner kind of breakup, though. The “clean escape” mentioned in the song seems inevitable, for the speaker feels “more like a stranger each time I come home.” The feelings are apparently mutual, since he starts the song by pleading, “If you walk away I’ll walk away.” “Landlocked Blues” isn’t just personal. It’s also political. While describing the emotional ambiguity of this difficult relationship, the song also comments upon American foreign policy. The speaker remembers sleeping with his partner, “with the noise in the background of a televised war/ And in the deafening pleasure I thought I heard someone say/ ‘If we walk away, they’ll walk away’.” Oberst brilliantly merges the protest and personal-narrative streams of folk music, giving us a cross between “Masters of War” and “Tangled Up in Blue.” “Landlocked Blues” is one weighty, complex breakup song. It’s a heckuva lot to cram into five minutes. – Jake Adams
“Bitch” by E-40 & Too $hort
For the breakup playlist I’d like to add Too $hort and E-40′s “Bitch” because some of you dudes in shitty relationships need to stop acting like bitches and break up already. - Chaz Kangas