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Post Valentine’s Day tunes to mend the heart

Was your Valentine’s Day a total disaster? Are you recently single for other reasons? If so, it’s always great to turn to classic breakup music. Throughout contemporary music’s history, songs about loss of love have dominated the charts. The breakup song has been an important and well-received artistic statement. Whether you’ve experienced some terrible luck with relationships, are recently single or are happily in love, you can find enjoyment in these classic heartbreak tunes.

1. The Rolling Stones — “Miss You”

On “Miss You” Mick Jagger sings about his prolonged obsession with a former love interest. It’s a Stones single for the ages and an essential track for the recently-single.

2. Marvin Gaye  — “Heard It Through the Grapevine.” 

The late Marvin Gaye is universally acknowledged as the all-time most important Motown artist. Gaye’s beautiful voice and songwriting style shines on this soul song. The lyrics revolve around jealousy and obsession in the midst of a recent split, but the instrumentation is undeniably uplifting.

3. Liz Phair  — “… and Run.” 

Years before her single “Why Can’t I” dominated the airwaves, Liz Phair released her brilliantly charming and frequently saddening debut album, “Exile in Guyville.” “Guyville” centers around Phair’s many failed relationships, and “… and Run” is the shining example of this.

4. Fleetwood Mac — “Go Your Own Way”

Long before Taylor Swift and Adele became the co-reigning queens of breakup music, Fleetwood Mac was breakup music’s ruling trio. The band’s legendary album “Rumors” devotes a lot of lyrics to discussion of relationship issues, infidelity and love in decline. “Go Your Own Way” isn’t a standout, but is still breakup material.

5. Kanye West  — “Welcome to Heartbreak”

“Welcome to Heartbreak” is not technically a breakup song, but it’s my favorite cut on Yeezy’s “808s and Heartbreaks” album — and “808s” is definitely a breakup album.

6. Taylor Swift  at least half of her discography. 

You can’t expect a sensible person to pick just one T. Swift breakup song. “I Knew Your Were Trouble,” “We Are Never Getting Back Together” and at least a dozen more Swift tracks are perfect listens for the recently-single.

7. John Mayer — “Heartbreak Warfare”

Who doesn’t love some John Mayer every now and then? The prolific pop rocker frequently sings about love, but he inverts his cash cow subject matter on “Heartbreak Warfare.”

8. Joy Division — “Love Will Tear Us Apart”

The seminal U.K. post-punk band’s’ biggest hit, “Love Will Tear Us Apart,” retells a story of lost love set to clean guitar, soft synths and a driving motorik-style rhythm.

9. The Smiths — “Heaven Knows I’m Miserable Now.” 

As a bonus, this is quite possibly my favorite song ever. The singing is incredible, bass and drums glue everything together. 

10. Elliott Smith — “Say Yes”

Elliott Smith’s solo career is built around pulling on listener’s heartstrings. He’s written more than a dozen perfect breakup songs, but “Say Yes” is the ideal starting point for those new to Smith.

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May 2, 2025

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