Month: July 2026

The Heartbreak Collection

If falling in love is the greatest feeling in the world, losing that love is life’s cruelest descent. It’s a plunge from the bright skies and exhilarating heights of a penthouse suite to the dark and dreary basement. Fortunately, the elevator music is fantastic.

Listed below are my favorite fifty songs that capture the sadness, despair, anger, and lament over lost love and wrecked romance. Whether you’re “living in the memory of a love that never was” or you’ve “thrown away the blues,” the lyrics of at least one of these songs probably express the emotion you’ve felt.

Photo by Logan Nance at Serendipity Public House in Midway, Kentucky

Am I feeling heartbreaky? Lovelorn? Romantically devastated? I am not. I’m in the happy days of a Mary Beth courtship (and marriage) that started in 1982. But I was once a teenager, and while the pangs of rejection and loss are a distant memory, they’re not forgotten. Psychoanalyze me if you will, but I have always gravitated toward music that speaks to the pain of lost love.

Not all heartbreak is the same, of course. Sometimes you never get the girl. Sometimes you do, but you blow it. Or she blows you off. And sometimes it’s just not in the cards. For that reason, I’ve broken these fifty songs of anguish—my Heartbreak Collection—into seven categories. Think of them as the seven stages of romantic loss.

I’ll add some comments after the list. For now, keep this in mind: I don’t claim this to be the definitive list of heartbreak songs. I’m saying only that it’s my list. Not only do the words tell a sad tale, the music itself resonates with me. These are songs I listen to … sing along with … and relish the emotion. As one says, I “guess I’d rather hurt than feel nothin’ at all.”

See if you feel something with this Heartbreak Collection.

Unrequited Love – loving someone who doesn’t know … or doesn’t reciprocate

  • Long Long Time – Linda Ronstadt
  • Two Out Of Three Ain’t Bad – Meatloaf
  • I Can’t Make You Love Me – Bonnie Raitt
  • Jessie’s Girl – Rick Springfield
  • You Don’t Know Me — Ray Charles

Regret – lamenting mistakes or missed opportunities

  • Just A Dream – Nelly
  • Careless Whisper  – George Michael
  • Sorry Seems To Be The Hardest Word – Elton John
  • Against All Odds – Phil Collins
  • She’s Out Of My Life – Michael Jackson
  • When I Was Your Man – Bruno Mars
  • Always On My Mind – Willie Nelson

Come Back, Please – hoping to rekindle a relationship that’s fallen apart

  • Don’t Leave Me This Way – Thelma Houston (also Harold Melvin & the Blue Notes)
  • Un-Break My Heart – Toni Braxton
  • Whatcha Say – Jason Derulo
  • Nothing Compares 2 U – Sinéad O’Connor
  • I Want You Back – Jackson 5
  • Ain’t No Sunshine – Bill Withers
  • Hard To Say I’m Sorry – Chicago
  • Kentucky Rain – Elvis Presley
  • I’ll Never Get Over You Getting Over Me – Exposé
  • Need You Now – Lady Antebellum

Broken Hearts – expressing anger, heartbreak, or devastation after trust is broken

  • He Stopped Loving Her Today – George Jones
  • Jar Of Hearts – Christina Perri
  • I’m Not The Only One – Sam Smith
  • Crying – Roy Orbison (also k.d. lang)
  • Vampire – Olivia Rodrigo
  • Don’t Speak – No Doubt
  • Goodbye To You – Scandal featuring Patty Smyth
  • She’s Got You — Patsy Cline

Moving On – accepting the end and turning the page

  • I Will Survive – Gloria Gaynor (also CAKE)
  • Operator — Jim Croce
  • Sail On – The Commodores
  • It Must Have Been Love – Roxette
  • Irreplaceable – Beyoncé
  • Since U Been Gone – Kelly Clarkson
  • Someone Like You – Adele
  • I Will Always Love You – Dolly Parton (also Whitney Houston)

Nostalgia – looking back with affection, wistfulness, or gratitude

  • Same Old Lang Syne — Dan Fogelberg
  • Southern Cross – Crosby, Stills & Nash
  • Yesterday – The Beatles
  • Again – Janet Jackson
  • The Dance – Garth Brooks

Couldn’t Make it Work – mourning a relationship that couldn’t survive

  • Brandy (You’re A Fine Girl) – Looking Glass
  • The Love I Lost – Harold Melvin & the Blue Notes
  • Worst That Could Happen – Brooklyn Bridge
  • Hello It’s Me — Todd Rundgren
  • The Winner Takes It All — ABBA
  • I Honestly Love You – Olivia Newton-John
  • Neither One of Us — Gladys Knight & the Pips

No one style or era of music can lay sole claim to heartbreak. My collection spans six decades of popular music. It includes country, soul, Motown, disco, classic rock, pop, hip-hop, alternative rock, and even a little funk. George Jones and Olivia Rodrigo, Nelly and Garth Brooks, Gloria Gaynor and the Beatles all tell a sad story. The tempo, instruments, and words vary, but every song travels to a bittersweet destination.

This list has fifty songs by fifty different acts … with two caveats. Michael Jackson appears both as a solo performer and as a member of the Jackson 5. Harold Melvin & the Blue Notes (with the incomparable Teddy Pendergrass on lead vocals) appears twice, but I went with Thelma Houston as the primary artist for “Don’t Leave Me This Way.”  

Three more dual-artist notes:

  • I Will Survive – Gloria Gaynor topped the Billboard chart for three weeks in 1979. I love the disco groove, driven by an open hi-hat snapping on the off-beats (a rhythmic feature also prominent on both versions of Don’t Leave Me This Way). Where Gloria Gaynor sings triumphantly, John McCrea of CAKE delivers the lyrics in halting, deadpan fashion that I find fascinating.
  • I Will Always Love You – Nobody sings with the power of Whitney, and her version is probably superior, but dammit, this is Dolly’s song, so I give her top billing.
  • Crying – This is Roy Orbison’s song, and he also recorded it as a duet with k.d. lang. She absolutely killed it, though, when she sang it solo. I again give top billing to the original artist, but in this case, I prefer the cover. 

I invite you to comment on my list and to add—or compile—your own heartbreak favorites. While none of these songs have a happy ending, I’ll leave you with a glimmer of light.

The songs in my Heartbreak Collection aren’t so much about heartbreak as what people do after their heart breaks. Some singers beg. Some blame. Others reminisce and survive, and a handful even grow. Let’s latch on to grow. We’ve all had our heart broken, and yeah, we probably could’ve done without the pain … but we’d have “had to miss the dance.”

Ninety-Six Percent Perfect

I drink hot coffee. Black. Every morning. Even in the summer.

I drink it for the caffeine fix, I suppose. I remember when Mr. Haynes, my fifth-grade science teacher at Midway Elementary, asked us to raise our hand if our parents drink coffee every morning. My hand went up. Both my parents sat at the breakfast table every morning, drinking coffee and reading the Lexington Herald.  

They’re addicted to a drug,” Mr. Haynes said.

Holy sugar substitute! I thought. My own parents … drug addicts. Mr. Haynes went on to explain that caffeine, while medically classified as a drug, is widely used and probably harmless.

Still, Mr. Haynes got my attention, and I paid close attention to the rest of his lesson on substances that change how the body or brain functions. I did not share any of that with my parents that night. I didn’t want them to feel like drug addicts.

And whether it was due to Mr. Haynes’s dramatic depiction of coffee or its less-than-welcoming taste, I didn’t drink coffee during my high school years. Neither did I drink coffee to power me through late-night study sessions in college, nor in my twenties to wake me up at work after a night out.

It was a boys trip to Las Vegas that put me onto coffee … that put coffee into me. Our trip preceded “The Hangover,” and our night was not nearly as insane, but it was debilitating enough to make me guzzle some coffee at the breakfast buffet. I was twenty-nine when I started drinking coffee, and I never stopped.

Hangover mornings are long past, but coffee remains. My day can go in a hundred different directions, but each one of them starts with coffee. Not every coffee morning is created equal, of course. A steaming mug of joe is one hundred percent perfect on a frigid wintry morning. But even when it’s far from cold—imagine a humid blanket of August air—a hot cup of coffee still hits me at about ninety-six percent perfect.

Picture this: It’s 2008ish, and I’m sitting with sleep-deprived adults in the rickety bleachers of a baseball field somewhere in Central Kentucky. The morning air is heavy, still laden, somehow, with the ball-field dust from last night’s games. The July day is forecast to hit a hundred degrees, and all of us parents have driven ninety minutes to deliver our young sons to the field by seven, an hour before the first game.

“These boys need to warm up,” the coach told us the night before at eleven-thirty, when the last game ended. “They’ll start sweating the second they walk out the door,” we insisted. We were powerless, though, as we dared not put our sons’ playing time at risk.

It’s eight minutes past seven, and the sun is already searing. The temperature is eighty-one. The Real Feel is one million. I have a large cup of McDonald’s coffee in my hand. Another is seated beside me. I am reading the Lexington Herald-Leader.

A baseball mom trudges in front of the bleachers. She stops in front of me. Stares at me. Incredulous. “How can you drink hot coffee on a morning like this?” She is not poking fun. She genuinely wants to know.

I lower my newspaper. I try to smile. “How can I not, Missy?”

And so it will always be. I’ve read article after article about the effects of coffee on human health. Through the years, I worried about the possible risks and exalted over the reputed benefits. None of the articles changed my daily habit, though. Today I enjoy all the benefits—improved alertness and a lowered risk of several serious ailments—and suffer none of the possible downsides: jitteriness, insomnia, and heartburn.

I’m no longer a baseball dad at sticky ball fields, but I still live in Kentucky, and it’s only getting hotter. I drink hot coffee every morning, though. I suppose I could switch to a hot-weather alternative and get my caffeine fix via iced coffee, cold brew, or a Frappuccino.

But I don’t. And what does that say about me? Am I so set in my ways that I won’t try a different solution? So rigid that I won’t vary my routine? Too frugal to drive through and buy a cooler version of my morning staple?

Yeah, maybe. I am sort of set in my ways. And I can be a bit of a cheapskate.

But the explanation lies elsewhere. I don’t try a different solution because I don’t have a problem. Ninety-six percent perfect is damn near perfect.

It’s hot outside, but I like to drink hot coffee, Missy.

Black. Every morning. Even in the summer.