heartbreak-songs-inside

It’s almost Valentine’s Day weekend, and nobody’s gonna let you forget it. Whether it’s a store filled with red foil-wrapped heart shaped everything or ads that shame us into ill-advised last-minute jewelry purchases, we’re all in store for a final 48 hours of schmaltzy sensory assault.

The biggest casualties of the assault aren’t our eyes, or truffle-clogged teeth, or even our wallets. It’s our ears, subjected for days—and weeks—to the maudlin, sentimental, angsty seasonal marathon of heartbreak music.

Some are oldies, some are newbies, but they all have one thing in common: they combine melody and vocals to remind us all that love can be really, really sad. Our solution: pair each song with the appropriate drink, something to either foil or just dig deeper into the manipulative musical sadness of it all. Not that we’re recommending overconsumption of alcohol on an already emotionally exhausting day. But if you have to listen to “Hello” one more goddam time, you might as well have a drink in hand.

Un-break My Heart, Toni Braxton:

The lyrics make it sound like a breakup song, but the video—featuring Tyrese Gibson doing some Tai Chi—tells a different, still super sad, story.

SADDEST LINE: Literally, the first line—“Don’t leave me in all this pain.”

CHEER UP FACTOR: In addition to doing Tai Chi, Tyrese wears a sheer white shirt.

PAIR WITH: A rich, sultry red California cabernet. Heavy, a lot to take in.

Hello, Adele:

Adele has an incredible voice, but she uses it like a walking human anti-pep rally.

SADDEST LINE: “There’s such a difference between us, and a million miles.”

CHEER UP FACTOR: The upsettingly poignant SNL parody.

PAIR WITH: Overproof gin. The song’s too much, you’ll need 57% ABV to bear it.

End of the Road, Boyz II Men:

A classic. Girlfriend’s a cheater, but boyfriendz (II men) are pleading for her to stay.

SADDEST LINE EVER: “Right now, I’m just in so much pain, baby, ‘Cause you just won’t come back to me will you?”

CHEER UP FACTOR: Classic sexy talk-singing, “Girl, I’m here for you…”

PAIR WITH: American brandy, something smooth and well-seasoned (but cheaper than you thought it would be, and yet you don’t wanna lose it…)

Beck, Lost Cause:

Easily one of the most depressing titles in all sad love song history. Simple narrative: Beck’s giving up on someone he loved.

SADDEST LINE EVER: “Tired of fighting, fighting for a lost cause.”

CHEER UP FACTOR: For some reason the video involves an exploding colorful Beck robot falling to Earth.

PAIR WITH: Something delicate but brooding like Beck, maybe an Oregon Pinot Noir.

Gotye, Somebody That I Used To Know:

Beyond being painfully overplayed, it’s a heart-wrenching depiction of the bitterness that can overtake a breakup.

SADDEST LINE EVER: Probably the basic “Now you’re just somebody that I used to know,” since it kind of sums up the sad outcome.

CHEER UP FACTOR: Naked bodies getting painted! You gotta wonder how they dealt with bathroom breaks…

PAIR WITH: A Belgian witbier, spicy and complex, plus Gotye (aka Wouter Andre ‘Wally’ De Backer) was born in Bruges.

Ex-Factor, Lauryn Hill:

The most painful questions that come up in a breakup put out there with the smoothest track ever.

SADDEST LINE: “I know what we got to do, You let go and I’ll let go, too. ‘Cause no one’s hurt me more than you, and no one ever will.”

CHEER UP FACTOR: This is a tough one. Hmmm. Lauryn Hill finally got out of jail for tax evasion?

PAIR WITH: Anejo tequila. Sit, sip, think of all the years that went into making something so beautiful that must come to an ened. Sigh…

It Must Have Been Love, Roxette:

A late ‘80s classic, as power-ballady as a song of heartbreak gets. (But yeah, high notes are hard to hit if you’re sobbing at karaoke.)

SADDEST LINE: “Yeah, it must have been love, but it’s over now. It was all that I wanted, now I’m living without.”

CHEER UP FACTOR: Random shots from “Pretty Woman” in the video.

PAIR WITH: Honor the original subtitle (“It Must Have Been Love: Christmas For the Broken Hearted”) with some mulled wine. Sorry, we meant “so much” mulled wine.

Pictures of You, The Cure:

Great song by a great band, but damn does this make us think twice about scrolling through Facebook pics.

SADDEST LINE: “If only I’d thought of the right words, I could have held onto your heart. If only I’d thought of the right words, I wouldn’t be breaking apart…all my pictures of you.”

CHEER UP FACTOR: Impromptu snowball fight between band and crew at the end of the video.

PAIR WITH: A tumbler of peated Scotch. Something with enough salinity and smoky aromatics to draw your attention away from pictures without totally interrupting some necessary brooding.

Without You, Mariah Carey:

Another beast of a voice—we’d like to see Adele v. Mariah, who can make us all cry hardest, longest—which pretty much cuts to the chase of total heartbreak despair.

SADDEST LINE: No contest. “I can’t live if living is without you.”

CHEER UP FACTOR: The song was originally written by Pete Ham and Tom Evans of the Brit rock band “Badfinger.” Just, enjoy the name.

PAIR WITH: Sauvignon Blanc. Possibly filled up closer to the top of the wine glass than usual. Easy to slurp down between brave attempts at following Mariah up the register.

Someone Like You, Adele:

Yeah, she made it onto the list twice (and probably could get a couple more spots.) Her first breakup hit, where she pledges to leave her ex alone and spend her emotional energy of finding a proxy. (No self-help montage here.)

SADDEST LINE: “Sometimes it lasts in love but sometimes it hurts instead.” No shit.

CHEER UP FACTOR: Adele crushing Nikki Minaj’s verse in “Monster.”

PAIR WITH: A Cremant, because you can’t have your favorite stand-by Champagne (everyone bought it up for V-Day liquid courage) so you’ll find some (bubbly) like it.

Love In Vain, The Rolling Stones:

No sadder, sweeter song. Also, like a couple Stones “classics,” totally lifted from Robert Johnson.

SADDEST LINE: “It’s hard to tell, it’s hard to tell, when all your love’s in vain.”

CHEER UP FACTOR: Jimmy Fallon as Mick Jagger. Pointin’ fingers.

PAIR WITH: Bourbon. Rich, deep, full of history and bittersweet southern grief.

Roses, OutKast:

Don’t pretend to understand the manic genius of OutKast, but when you bust up Andre 3000’s heart, this is what happens.

SADDEST LINE: “Roses really smell like poo-poo-poo.”

CHEER UP FACTOR: He recovered.

PAIR WITH: Whatever Andre 3000 hates, ‘cuz he seems to be fine calling a girl who rejected him “bitch” in probably every manifestation possible. You got broke up with. Don’t be a bitch.

Again, Janet Jackson:

Janet can make us feel plenty empowered. And hell yes. Sometimes, she’s tender. Melt into this.

SADDEST LINE: “How can I be strong? I’ve asked myself, time and time again.”

CHEER UP FACTOR: Janet Jackson’s abs. Also, patriotism.

PAIR WITH: Apologies to wine geeks and just, yeah, well, haters of sweet. But this song is so goddam sad and poignant, we’re doing box white zin on the shoulder as we listen. ‘Cuz, honestly, sh*t.

I Will Survive, Gloria Gaynor:

We’re shutting down the Valentine’s/breakup bullsh*t with a musical emotional middle finger to the personal necessity of maintaining a relationship.

BEST LINE: “Now I’m savin’ all my loving for someone who’s loving me.”

CHEER UP FACTOR: This is the cheer up factor.

PAIR WITH: Whatever celebratory drink you are ready for.