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The Heartfelt (And Sometimes Hilarious) Legacy of Songs About a Son: When Music Remembers Boys We Loved

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November 10, 2025
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Sons in Song: An Emotional Soundtrack with Surprises

Whoever said pop songs were all about breakups, makeups, or that wild night in Vegas clearly hadn’t spent much time flipping through the songbook of tributes written for sons. And, as the world recently discovered thanks to Taylor Swift’s ‘Ruin the Friendship’, these tracks aren’t just tearjerkers—they’re often packed with awkward school dances, mysterious friends named Abigail, and enough unspoken feelings to power a therapist’s next five sessions.

So, let’s crank up the amp and take a (chirpy but sentimental) stroll through the surprisingly rich genre of songs about a son. Yes, there will be misty eyes. But there may also be dance moves that should’ve stayed in the 2000s.

Taylor Swift and Her Unfinished Goodbye

Enter Taylor Swift’s ‘Ruin the Friendship’, which became the talk of the town—and not just because fans love decoding clues like cryptographers on caffeine. When Susan Lang, a Tennessee mom, heard the track, something clicked: those longing lyrics, mentions of prom regret, and a quiet acknowledgment at a friend’s grave all pointed, in her mind, to her late son Jeffrey Lang. Cue the waterworks—and some pretty moving gratitude.

Taylor and Jeffrey weren’t just classmates. They were comedic partners-in-crime, sharing late-night songwriting sessions and practical jokes. When Jeffrey died at 21, Swift publicly mourned her friend at the BMI Awards, stating, “Yesterday I sang at the funeral of one of my best friends… He was 21, and I used to play my songs for him first.”

‘Ruin the Friendship’ became a vessel for memories—of missed kisses, abandoned chances, and, as Swift laments, the tragedy of a friendship that never became more. The song advises: “My advice is always ruin the friendship / Better that than regret it / For all time / Should’ve kissed you anyway.” Clearly, not all advice is made for greeting cards, but for Susan Lang, it was proof her son’s life continued to echo through art.

The Universal Appeal: Everyone’s Got a Son (Even If It’s Their Neighbor’s Kid)

Of course, Taylor Swift isn’t the only artist to immortalize sons in song. It’s a genre that’s as old as family drama: from John Lennon’s raw honesty in ‘Mother’—okay, that one’s technically about moms, but bear with us—to Stevie Wonder’s iconic ‘Isn’t She Lovely’ (which, fun fact, is actually about his newborn daughter but is so heartfelt, it might as well be about every child ever). Clearly, musicians can’t resist the urge to put family on vinyl.

And when the lyrics zoom in specifically on sons, it tends to get personal. There are stories of estrangement (‘Cat’s in the Cradle’), wild adventure (‘Simple Man’ by Lynyrd Skynyrd), or humble pride (‘A Song for My Son’ by Mikki Viereck—a wedding DJ staple that bravely faces the threat of mascara streaks). Taylor’s approach is unique: blending regret, nostalgia, and just a dash of high school melodrama. It’s the musical equivalent of an old yearbook signed “Stay cool!” with a secret wish for more.

Why “Songs About a Son” Hit Home (And Your Funny Bone)

There’s something inherently comedic about the way artists approach sons in song. Maybe it’s the awkward teenage years, the questionable haircuts, or the universal experience of wanting to say more than we ever did. Swift’s prom reference—where she wishes she’d gone with Jeffrey rather than someone else—could’ve been straight out of a John Hughes movie. The songs remind listeners that even pop stars are not immune to regrets left unsaid or dances never danced.

And then, there’s the mother’s perspective. Susan Lang’s belief that Swift was singing about her son is heartwarming and slightly hilarious—imagine keeping an old high school photo of your child and Taylor Swift on the mantle, waiting for the next cryptic lyric to confirm your suspicions. For fans and mothers everywhere, songs about a son are bittersweet time machines—taking them back to playgrounds, awkward teenage years, and late-night phone calls to friends who will forever be young in memory.

The Not-So-Secret Power of Music: Keeping Memories Alive

What these tracks prove is that music’s real magic isn’t in the chords—it’s in how they preserve the people we’ve loved. In Susan Lang’s words, Swift has “kept his name alive.” Whether it’s a hit single or an unreleased demo, the emotional resonance is the same. The laughter, the drama, the regret, and the pride—all immortalized for audiences who may never meet the person but feel like they’ve known him forever.

The added twist: Swift’s lyrics make room not just for her personal grief, but for every listener holding on to a story of a son, a friend, or a chance they let slip away. The universal longing (and let’s face it, a few universal facepalms at missed opportunities) make these songs comforting and cathartic. No one needs to be a celebrity to feel the sting of “Should’ve kissed you anyway.” But it takes a true pop icon to turn embarrassment into an anthem for the masses.

Songs About a Son: Where Legacies Live (And Sometimes Dance)

So, what have we learned? That songs about a son are more than just sentimental background music. They’re living memorials, often hilarious reminders of all the dumb things we did as teenagers, and proof that love (or regret) can make music truly timeless.

And if you take nothing else from this genre, let it be this: never skip out on the chance to ruin a friendship with a little more honesty (and, maybe, a prom date with fewer regrets). Taylor Swift and Susan Lang have shown us that a simple song can resurrect memories, heal hearts, and, yes, occasionally poke fun at our own hesitancy.

So next time you hear a melody wafting out of your speakers, pause and ask: is this about a son? Who knows. But it just might be a sign to hug your own—and maybe even tell your best friend you should’ve kissed them at prom after all.

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