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14 Songs About Heartbreak for Your Sad Valentine’s Day

<> on January 9, 2010 in Sydney, Australia.

Don’t believe the hype: Love stinks, and no day reminds you of its follies quite like Valentine’s Day, as marketers fall over themselves to remind you you’re really on your own. To make the occasion, we’ve collected some of our favorite sad songs about heartbreak to console you on this cold winter day.

Eels, “Hey Man (Now You’re Really Living)”

This casual, jingly Eels tune from 2005’s Blinking Lights and Other Revelations is a heartbreak song precisely at the midpoint of sarcasm and sincerity. Each repetition of the title sounds bitter as hell, and also like holy reverence for the whole spectrum of human emotion: “Do you know what it’s like to care too much / ‘Bout someone that you’re gonna never get to touch? / Hey man, now you’re really living.” It’s hard to take pleasure in sadness when you’re looking up from the bottom, but “Hey Man” is a treasure that outlasts the lows. — ANNA GACA

Various Artists, “It Never Entered My Mind”

Songwriting team Richard Rodgers and Lorenz Hart wrote one of the greatest love ballads of all time back in 1940, and since then, there have been countless excellent recordings of it. It’s hard to pick a favorite: The melancholic takes Ella Fitzgerald and Frank Sinatra released in the 1950s are probably the ideal versions, but there’s also Miles’ iconic trumpet rendition, which helped solidify the song’s place as one of the most poignant jazz standards of all-time. Hart effortlessly situated dozens of his lyrics perfectly on the line between despair and absurd humor, assisted by ingenious, bizarre rhyme schemes. I don’t understand you if you don’t agree that “You had what I lack myself/Now I even have to scratch my back myself” is one of the saddest, greatest couplets ever written. Here’s an underrated, muted version by Peggy Lee that’s perfectly suited for a gray Valentine’s Day. — WINSTON COOK-WILSON

Al Green, “For the Good Times”

If you don’t listen closely, you might not realize “For the Good Times” is a song about heartbreak, and not everlasting love. The chorus begins with a watercolor scene of a couple in bed, holding each other close and taking shelter from a drizzly day. Then, the final couplet reveals that the soul of the relationship has already escaped through the window, and this might be the lovers’ final afternoon in each other’s arms: “Make believe you love me, one more time / For the good times.” Kris Kristofferson, who wrote “For the Good Times,” suffused his version with heartache, beginning with the uncertain shake in his voice in the opening lines. Ray Price, who made it a number one hit on the country charts a few years later, followed suit.

Al Green and his longtime producer Willie Mitchell double the length of Kristofferson’s original, refashioning from country ballad into symphonic soul opus. The longing is still there, carried by Green’s unparalleled restraint as a vocalist. But he and his backup singers make the couple’s final embrace sound like the height of ecstasy, rendering the kicker all the more crushing when it finally arrives. Green’s version stands out for showing you just how good the good times really were. — ANDY CUSH

The Magnetic Fields, “You’re My Only Home”

If you’ve never found yourself on the powerless end of a longterm relationship that’s falling apart before your eyes, well—I haven’t either, but I imagine it’s awful. Of the many Magnetic Fields songs that document such resignation, “You’re My Only Home” has stuck with me the longest because of its despairing chorus: “When you cancel dinner plans/when you cross the street and you don’t take my hand/ when you make impossible demands/I wish I didn’t understand.” Bracketed by earnest declarations of devotion, the sad song’s center reveals its narrator to be a realist, someone who understands that whatever relationship he’s in is already over—that even if he isn’t technically alone, he’s on his own. Also, the way Stephen Merritt drops his voice when he croons “street” makes me grin every time. — TAYLOR BERMAN

NSYNC, “Tearin’ Up My Heart”

This is the first song about heartbreak I remember really being affected by. There’s never been a point in my life since its release that I haven’t been able to sing its chorus, and the damaged sweetness of boy band vocals are particularly good at conveying this sort of infinite internal turmoil. — JORDAN SARGENT

Aaliyah, “We Need a Resolution” ft. Timbaland

In which Timbaland the No Good, fed up with the drama, decides to abandon his girl for a night out, as he justifies himself with a charismatically corny verse—“I’m tired of these scars!”—that rides off the defense of wounded masculinity. I suppose confronting that hurt would be the noble course of action here, but this verse consoles me because of its moral: Life is too short not to be petty. It’s an easy mantra to remember when an ex removes you from Facebook or what-have-you. I will keep shining, boo. — BRIAN JOSEPHS

The Mountain Goats, “Game Shows Touch Our Lives”

Tallahassee is a devastating album about the death throes of a married couple’s relationship, but no song locates the heartbreaking mix of tenderness and bitterness involved with a protracted breakup like “Game Shows Touch Our Lives,” in which the couple watches game shows while getting stupid drunk. Darnielle’s narrator hands his soon-to-be-ex-wife a bottle of liquor, and delivers a heartbreaking, unadorned line: “People say friends don’t destroy one another / What do they know about friends?” Nobody can hate you better than someone who’s seen your best side, and judged it against your worst. — JEREMY GORDON

Tullycraft, “Pop Songs Your New Boyfriend’s Too Stupid to Know About”

As if getting dumped weren’t bad enough, the person they left you for inevitably has basic taste in music. The “new boyfriend” has almost certainly heard of Neutral Milk Hotel by now—this song is from 2000—but the point stands. Cold comfort when you run into your ex’s new boo at a concert for a band you introduced them to first. — ANNA GACA

Randy Newman, “Living Without You”

“Living Without You” is a perfect and devastating sad song that describes the hopelessness that follows a difficult breakup, the feeling of suddenly being alone with no end in sight. The Nilsson cover is excellent, as are Newman’s stripped-down versions, but there’s no comparison to the original, with its crescendoing orchestration matching the rising desolation of Newman’s voice. — TAYLOR BERMAN

Bloc Party, “Like Eating Glass”

“It’s so cold in this house,” Kele Okereke sings at the beginning of “Like Eating Glass,” crying with a sense of finality. The entire track, Bloc Party’s debut album’s opener, details a relationship that’s been derailed by natural courses rather than a misfortune. It’s a fate that awaits all romance; we kiss with “crosses on our eyes.” Love is bad, actually. — BRIAN JOSEPHS

D’Angelo, “One Mo’ Gin”

“One Mo’ Gin” is less about heartbreak than it is the sort of wistful memories you keep of someone who was meant to only pass through. There is something about the way in which D’Angelo’s vocals linger over the quite cheery arrangement, as if he’s really savoring thinking back on a closed chapter of his life. That can be fun, but the emptiness attached to that sort of natural passage of time can really hollow you out, too. — JORDAN SARGENT

Liz Phair, “Divorce Song”

Couples fight for a million reasons, but it’s particularly exhausting when an argument arises out of a misunderstanding. Liz Phair just wants to get a different hotel room at the end of a long drive, but her quasi-boyfriend takes it the wrong way and launches into a litany of reasons why this isn’t working out. In her husky, deeply weary voice, Phair apologizes for not being more attentive to how her tossed-off words could be conceived, then admits a deep hurt at how personal the fight turns: “But when you said that I wasn’t worth talking to / I had to take your word at that / But if you’d known how that would sound to me / You would’ve taken it back / And boxed it up and buried it in the ground.” Her singing is as clear and cool as a stream of river water, and the heartbreak of being able to diagnose a problem but not prevent it is felt acutely. — JEREMY GORDON

Townes Van Zandt, “Snowin’ on Raton”

In impressionistic fashion, “Snowin’ on Raton” tells the story of a man traveling through a snowstorm near the southern tip of the Rocky Mountains. We don’t really know where he’s going, or where he’s coming from. “You cannot count the miles until you feel them / And you cannot hold a lover that has gone,” Van Zandt sings to his hero. From that gnomic advice, it sounds like his partner has left him behind, and he’s headed off in a pursuit that may turn out to be futile. Beyond that, we only have haunting imagery: silent towns where the wind doesn’t blow and the moon doesn’t rise, mountains sleeping beneath blue and green blankets. My favorite version was recorded live in 1984, with Blaze Foley singing sweet harmonies over Van Zandt’s shoulder. Each man is a Texas country original who plumbed the depths of loneliness in his songs, who led a boozy, wayward, and sometimes tortured life, then died well before his time. Hearing them sing through the VHS static and watching the stage lights glint and flicker off the studs in Foley’s hat, it’s easy to imagine them on their own journey through the mountains, just emerging from the snow. — ANDY CUSH

Harry Nilsson, “Don’t Forget Me”

A broken love song on Harry Nilsson’s most broken-sounding album, “Don’t Forget Me” is a true beacon in Nilsson’s discography. (It’s also guaranteed to bring tears to my eyes if I put it on alone and sink into it too fully.) The gently orchestrated piano ballad sounds like it was dashed off in a day–the album, a collaboration with John Lennon on his “Lost Weekend,” was only made in a few–but the lyric is pulled straight from a vein: “In the summer by the poolside/While the fireflies are all around you/I’ll miss you when I’m lonely/I’ll miss the alimony too.” — WINSTON COOK-WILSON