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Dolly Parton Names Her Worst Songs Late Night With Conan Obrien

The Question: Does a Legendary Career Require a Few Missteps?

By Marcus Bell· October 25, 2026· 2-part storyOriginal fiction
Dolly Parton Names Her Worst Songs Late Night With Conan Obrien
Dolly Parton Names Her Worst Songs Late Night With Conan Obrien

Part 1

The Question: Does a Legendary Career Require a Few Missteps?

You have probably seen the trailer for Dolly Parton's latest album, the patriotic *For God and Country* (2023), or maybe you caught the buzz around her rock opus *Rockstar* (2023). But here's the real question: after 73 albums, can a legend afford a few duds? Dolly Parton has released 73 albums over her six-decade career, a number she confirmed in a recent interview. That's not a typo. Seventy-three. From her 1967 debut *Hello, I'm Dolly* to her 2023 rock album *Rockstar* and her patriotic collection *For God and Country*, she's been a constant force in music. But with that volume comes the inevitable: some songs just don't work. And that's okay. In fact, it might be essential.

Dolly herself has a refreshingly honest take on this. When asked if she ever regretted any of those 73 albums, she laughed and said, "When you're a songwriter you think they're all good... it's like how everybody thinks their kids are pretty even if they're not." That's the kind of self-awareness that separates a legend from a mere hitmaker. She knows not every track is a "Jolene" or a "9 to 5." But she also knows that creativity isn't about batting a thousand. It's about swinging for the fences, even if you occasionally strike out. And strike out she has—by her own admission.

Take "I Want to Throw Rocks at Her," a song she wrote early in her career. The premise? A woman so bitter about losing her man that she'd rather throw rocks at the new bride than rice at the wedding. Dolly cringes at it now, calling it a misstep. But she also recognizes it as part of her journey. "I got some suckers in there," she admitted. That's the thing about a 73-album career: you're going to have some suckers. But those suckers don't define you. They refine you.

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So the question becomes: does a legendary career require a few missteps? Look at the evidence. Willie Nelson has released over 70 albums, and while classics like *Red Headed Stranger* (1975) and *Stardust* (1978) are revered, he's also put out plenty of forgettable records. The Rolling Stones have 30+ studio albums, and not all of them are *Exile on Main St.* (1972). Prince released 39 studio albums in his lifetime, and even die-hard fans will admit that some of his later work didn't reach the heights of *Purple Rain* (1984) or *Sign o' the Times* (1987). Yet none of these artists' legacies are diminished by their lesser moments. If anything, the sheer volume of work makes their peaks even more impressive.

Bob Dylan is perhaps the best example. His 1970 album *Self Portrait* was so poorly received that critic Greil Marcus famously opened his review with, "What is this shit?" His 1988 album *Down in the Groove* was equally panned. And yet, Dylan is still Bob Dylan. He's still the Nobel Prize winner, the voice of a generation, the man who wrote "Like a Rolling Stone." Those missteps didn't tarnish his legacy; they became footnotes, curiosities for completists. They proved that even geniuses are human. And that's precisely what makes them relatable.

Dolly Parton is no different. She's had her share of albums that didn't connect, like 1980's *Dolly, Dolly, Dolly* or 1985's *Real Love*. But she's also given us *Jolene* (1974), *Here You Come Again* (1977), *9 to 5 and Odd Jobs* (1980), and the *Trio* albums with Emmylou Harris and Linda Ronstadt. Her recent output proves she's still taking risks. *Rockstar* (2023) saw her collaborating with everyone from Paul McCartney to Lizzo, while *For God and Country* (2023) leans into her patriotic side. Not every track will be a classic, but that's not the point. The point is that she's still creating, still pushing, still surprising us.

In a culture obsessed with perfection, Dolly's willingness to fail is radical. It's a reminder that art isn't about avoiding mistakes; it's about making them boldly. As she put it, "You've always got... when you're a songwriter you think they're all good." That belief—however misguided—is what fuels a 73-album career. Without it, she might have stopped at one. Or ten. But she didn't. She kept going, and in doing so, she built a legacy that's not just about the hits, but about the sheer, unapologetic act of creation.

So, can a legend afford a few duds? Absolutely. In fact, they might be necessary. They're the price of admission for a career that spans decades, genres, and generations. They're proof that even the greats are willing to risk embarrassment for the sake of a song. And if you're Dolly Parton, with 73 albums and counting, you've earned the right to throw a few rocks—even if they don't always hit the mark.

The Answer, Part 1: Even Legends Have Their 'Cowboy Pervert' Moments

So you’ve heard the question: does a legendary career require a few missteps? Dolly Parton has 73 albums. That’s not a typo. And among those 73, there’s at least one she’d probably rather forget. When asked about her least popular album, she laughed and called it “me as the cowboy pervert.” She didn’t name it, but the internet has its theories. The most likely culprit? *Burlap & Satin* (1983) or *The Great Pretender* (1984). Both were commercial duds, but they’re also fascinating artifacts of an artist willing to swing big and miss.

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This story is original fiction. Names, characters and details are invented, and nothing here is legal, medical or financial advice. Share it if it reminded you of someone.

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