Breaking Up Is Hard to Do

Sometimes you’re the windshield; sometimes you’re the bug. This bit of philosophical wisdom was imparted to me long ago by a guy whose name I don’t remember, nor can I recall the breakup. I suspect that in this case, I was the windshield.

Indeed, sometimes a romantic breakup feels like ballast thrown overboard so your ship can sail, baby, sail. And sometimes, breakups pierce the heart and wound the spirit forevermore. This is the stuff of poets and songwriters — the “see ya” and “ciao” and “so long” to lost amours. or maybe the ones you didn’t appreciate until they walked out that door. Now you’re sorry. So classic.

Breakup songs have always been about the important things like love won, then love gone. Sometimes breakups are wistful and sometimes they’re full-on insane, and on some occasions they’re mutual and that’s the rare win-win. Don’t dismiss the subject as cliché because it’s not — not if breaking up happens to you.

Here are the top 10 breakup songs from back then and now, because breaking up is timeless.

1. “It’s Over” – Roy Orbison

Elvis Presley called Orbison “the world’s greatest singer.” Orbison wrote “Only the Lonely” for Presley, but then went on to record it himself, singing in his trademark three-octave range that Elvis called “the perfect voice.” After a lengthy musical hiatus, he joined the Traveling Wilburys — probably the most exclusive VIP “boy” band there ever was.

2. “Wild World” – Cat Stevens

Stevens rejected enormous commercial success and changed his name after converting to Islam. “Wild World” appears on his wildly successful album Tea for the Tillerman, and he says about the song, originally written after a two-year relationship ended, “I’m basically talking about myself in this one.” Now called Yusuf / Cat Stevens, he recently released Tea for the Tillerman 2 and will be touring with son Yoriyos and their band.

3. “Hey, That’s No Way to Say Goodbye” – Leonard Cohen

Like other songs penned for Marianne Ihlen, for example, “So Long Marianne,” Cohen knew how to say goodbye and write about it too with these poetic lyrics. He left their idyllic life together on Hydra and moved on to ever-increasing fame.

4. “Je Suis Venu te Dire Que Je M’en Vais [I Came to Tell You That I’m Leaving]” – Serge Gainsbourg

Gainsbourg is beloved by the French (and the rest of the Francophile world too), and in this classic song, some of the lyrics are inspired by France’s great poet Verlaine. The words attest to the difficulties of the long goodbye and because it’s in French, well, saying good-bye sounds sexy too.

5. “I Will Survive” – Gloria Gaynor

This anthem of the disco age made a person stand taller and feel stronger — and maybe feel like a better dancer too! An early ode to female empowerment, the lyrics reframe breakups to make women — or anyone, for that matter — winners of the heartbreak game. The song packed the dance floor, and still does, like no other.

6. “By the Time I Get to Phoenix” – Glen Campbell

Glen Campbell singing Jimmy Webb’s tune led to Campbell’s album of the same name taking home the very first Grammy Award for a country music album. The song’s inspiration came from Webb’s girlfriend leaving him and going on to marry someone else. When Webb himself sings the song as a soulful ballad, it attests to his status as one of the most gifted musical artists of his time. (And Isaac Hayes did perhaps the most soulful version.)

7. “The Shadow of Your Smile” – Johnny Mandel and Paul Francis Webster

A gently wistful approach to the breakup, the lyricist Paul Francis Webster penned this song for the film The Sandpiper. It was awarded a Grammy and Oscar. Of the many artists covering “The Shadow of Your Smile,” Sarah Vaughn does a heart-wrenchingly smooth and pristine version.

8. “Crazy Ex-Girlfriend” – Miranda Lambert

I once had a friend who had a near-fetish for what he called “crazy chicks.” He was equal parts awe-struck and afraid of them, as though they were fearsome goddesses toying with mere mortals. Maybe they were. Lambert’s revenge tune is an upbeat call for acting out and being damn proud of it too.

9. “Lost on You” – LP

After years of writing songs for acclaimed artists like Celine Dion and Rhianna, Laura Pergolizzi or LP, stepped into the limelight herself with a breakout hit that topped the charts in Europe. Her deeply musical talent and charismatic stage presence have garnered cult followings here and abroad.

10. “Drivers License” – Olivia Rodrigo

Delivered in a distinctively girlish voice, the song struck a chord with lyrics that describe the residual effects of a breakup, like driving around the ex’s neighborhood and imagining they’re still together. The song broke Spotify streaming records twice and was number 1 on the Billboard Hot 100 chart.