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1. “I Will Always Love You” – Dolly Parton (1974) > Whitney Houston (1992)
Let’s settle this: Yes, Whitney’s version is iconic, but Dolly wrote it, sang it with heartache only a country queen could deliver and did it without vocal pyrotechnics. It’s simple. It’s pure. It’s better.

Dolly Parton
Dolly Parton at the MGM 2016

2. “Hurt” – Johnny Cash (2002) > Nine Inch Nails (1994)
Trent Reznor may have penned it, but when The Man in Black sang, “Everyone I know goes away in the end,” it was chillingly real. Even Reznor admitted: “That song isn’t mine anymore.”

Remembering Johnny Cash!
Johnny Cash 1971

3. “The Gambler” – Kenny Rogers (1978) > Don Schlitz (1976)
Don wrote it and tried it first, but Kenny owned it. That gravelly wisdom? The poker-table metaphor? Instant legend. Rogers didn’t just sing “The Gambler”, he became him.

Kenny telling Don, ‘I got this’

4. “Tennessee Whiskey” – Chris Stapleton (2015) > David Allan Coe (1981)
Sure, Coe’s version was the OG and George Jones tried too, but when Stapleton belted it out soul-first at the CMAs, jaws dropped. His blues-soaked version redefined the modern country ballad and a hit #1.

Chris Stapleton Live at the Houston Rodeo - March 16, 2023
Chris Stapleton the Houston Rodeo 2022

5. “Take Me Home, Country Roads” – Toots & the Maytals (1973) > John Denver (1971)
Hold up. Reggae better than Denver? Yep. Toots Hibbert’s Caribbean-flavored cover gave his country classic a swaying, soulful vibe that made even West Virginians groove.

Photo of TOOTS & The MAYTALS
Toots in the early ’70’s

6. “Blue Ain’t Your Color” – Jessie James Decker (Live Cover) > Keith Urban (2016)
Keith’s original is smooth, no doubt. When Decker stripped it down with smoky vocals and real heartbreak, she turned it into something raw and sultry. Her version feels like it hurts more.

60th Academy of Country Music Awards - Arrivals
Jessie James Decker all sparkly in 2025

7. “Jolene” – The White Stripes (2004, Live) > Dolly Parton (1973)
Yes, we’re saying it: a garage rock band out-twanged Dolly. Jack White’s furious, pleading wails made Jolene sound like a supernatural force and the stripped arrangement put the desperation front and center.

072307 Boston, MA Jack and Meg White of the White Stripes perform at Agganis Arena on Monday, 7 2007. Staff Photo by Matthew West
Out of Detroit, The White Stripes early 2000’s


Final Chord
Covering a country classic is risky mess it up, and fans will come for you, but these seven artists didn’t just honor the originals, they elevated them. Whether by adding grit, soul or flat-out power, these covers prove one thing: in country music, the second shot can hit harder than the first.