Dolly Parton’s iconic hit didn’t just conquer the charts—it also left a lasting mark on mainstream music. Since its 1973 release, this enduring classic has been reimagined by artists born long after it first mesmerized listeners. Interestingly, Parton has revealed that the inspiration behind “Jolene” is a blend of a bank teller and a fan she encountered at one of her shows.

Songwriting duo Dewayne Blackwell and Earl Bud Lee, renowned for their knack for hit-making, handed this musical treasure to a rising star named Garth Brooks. Though still early in his career, Brooks’ commanding vocals and magnetic stage presence propelled the song to No. 1 on the charts. This breakthrough not only highlighted the duo’s songwriting brilliance but also launched Brooks into stardom, cementing his place as a country music powerhouse.

Celebrated in his later years as the greatest living country singer, George Jones amassed an extraordinary collection of chart-topping hits throughout his legendary career, securing his place in music history.

Among his many achievements, his 1999 cover stands out as one of his most moving and masterful performances, perfectly blending heartfelt lyrics with his soulful delivery. Like much of his work, this track continues to resonate with listeners, reflecting the timeless charm and lasting legacy of Jones’s musical brilliance.

In this heartbreaking story of a young girl trapped in a world of abuse, McBride’s smooth, soaring vocals bring raw emotion and unrelenting intensity to the 2002 track. This song took her signature girl-power anthems to new heights with its poignant, powerful message—and it’s a captivating masterpiece from beginning to end.

The late Charley Pride was a trailblazer who broke through country music’s color barrier, a groundbreaking achievement in its own right. However, focusing only on the challenges he overcame—or the genre’s limitations—overshadows the core of his legacy.

Pride was one of the most gifted songwriters in country music, and his biggest hit, a vibrant, fiddle-driven piece of soulful country, showcases the remarkable talent that earned him a place among the legends. One listen, and it’s clear why he stands with the greats.

Nearly every American can answer the question Jackson poses in this song: Where were you on September 11, 2001? Although conflicted about benefiting from such a tragedy, Jackson channeled his emotions into the music. In doing so, he provided a space for survivors and listeners to process their grief—and they expressed their gratitude in return.

While it addresses a serious theme, this lively, hip-swaying track finds McGraw poetically celebrating the importance of embracing life to the fullest. Both the song and its video dominated the 2004 CMAs and ACM Awards, delivering plenty of bucket list inspiration—though you might want to pass on the bull riding!

Mark Sanders and Tia Sillers created a heartfelt anthem that has become a cherished staple at father-daughter dances across the country. When Womack lent her voice to this moving track in 2000, it resonated deeply with listeners, ultimately earning her a Grammy for its powerful impact.

Even more legendary than her earlier smash hit “D.I.V.O.R.C.E,” Tammy Wynette’s magnificently melodramatic classic encouraged women to stand by their man “even though your heart is breaking.” While its feminist undertones have stirred debate over the years, a softer reading interprets it as a call for pragmatic compromise rather than blind submission.

And, of course, who could forget that unforgettable line: “After all, he’s just a man”?

Undoubtedly among the greatest songs ever influenced by a telephone engineer, Wichita Lineman emerged when songwriter Jimmy Webb was driving through rural Oklahoma. During his journey, he noticed a solitary man atop one of the countless telegraph poles stretching across the landscape.

This fleeting encounter inspired the creation of a timeless classic—an ethereal and poignant tribute to the solitude and quiet dignity of the working man.

Often underrated in the country music landscape, Kristofferson struck gold with this iconic track, perfectly distilling the haze of a hungover morning wander through town. As the song progresses, what begins as simple cravings for weed and fried chicken transforms into a bittersweet meditation on missed opportunities, cementing its status as a timeless classic.

While Johnny Cash’s rendition may have garnered more fame—much like how Me & Bobby McGee became synonymous with Janis Joplin—the unfiltered sincerity and longing in Kristofferson’s original ensure its enduring role as a cornerstone of the genre.

This 1971 tribute to West Virginia quickly became Denver’s signature hit. Though today it’s the perfect Instagram caption for any scenic, winding road, the song originally climbed to the second spot on Billboard’s Hot 100 and inspired a wave of cover versions in its honor.

Surprisingly, Cline wasn’t immediately drawn to the song crafted by Alan Block and Donn Hecht, but it went on to become her breakthrough hit in 1956. With a gentle, understated delivery, she breathes life into the lyrics, capturing the bittersweet longing of a woman yearning for true love and adding emotional weight to the melody.

Reba’s rendition of Bobbie Gentry’s 1969 classic breathed new life into the rags-to-riches story of Fancy Rae Baker. The captivating music video added depth to the narrative, while the song became Reba’s signature encore.

Fans eagerly anticipate the moment mid-performance when she dramatically unveils a dazzling red dress from beneath a black coat—a show-stopping move that never fails to excite.

“Breathe” became a massive crossover hit, marking Hill’s seventh number-one on the country charts in 1999. This mid-tempo anthem of budding love and romance enchanted listeners, securing a place on the Billboard Hot 100 for more than a year.

Carrie Underwood’s no-nonsense remedy for infidelity quickly became an anthem for the heartbroken—and maybe the overly dramatic too. With its strikingly vivid revenge narrative, the song captivated listeners and struck a chord with anyone who’s felt the sting of betrayal.

This bold track not only launched her from American Idol success to the pinnacle of country stardom but also cemented her status as a masterful storyteller in the music world.

Legendary country-folk artist Willie Nelson stole the spotlight with this track after making a name for himself as a songwriter for others. This beloved tune, portraying a gentle farewell, has been covered by numerous artists, but Nelson’s rendition endures as a timeless classic cherished by fans.

In this empowering anthem, Kacey Musgraves encourages women to push back against the patriarchal expectations imposed on them. The song gained attention for its unapologetic pro-LGBTQ+ message, including the bold line, “Kiss lots of girls, if that’s what you’re into,” which was notably censored during the Country Music Association Awards.

Loretta Lynn found inspiration close to home for her iconic 1969 hit, which became her signature song. This autobiographical masterpiece reflects the singer’s emotional struggles and love-filled upbringing in Kentucky, inspiring not just an album, but also a book and a feature film bearing the same title.

Australian country rocker Keith Urban offers a heartfelt anthem about the longing for love in this single from his 2002 album Golden Road. The song gained widespread popularity after being remixed for the 2003 romantic comedy How to Lose a Guy in 10 Days. Though the movie leans into the cheesy side, the track remains a must-listen.

Known for its rapid-fire, almost spoken-word delivery, the band’s original rendition became iconic, thanks in part to its spotlight on the Urban Cowboy soundtrack. This electrifying track tells the ultimate tale of a showdown with the devil, as Johnny and his fiddle go head-to-head with a soul-hungry Satan.

Written in 1995 by Ohio singer-songwriter Kim Richey and Angelo Petraglia, this deeply captivating song explores the haunting depths of a woman’s lifelong heartbreak. Mindy McCready’s 1997 cover reinvents the original, adding a shimmering pop gloss to its signature dusky melancholy.

Brad Paisley’s unforgettable duet with Alison Krauss tells the poignant story of a heartbroken man’s desperate last attempt, signaling the bittersweet close of a love story.

This emotional masterpiece struck such a powerful chord that it earned double Platinum certification from the RIAA, highlighting Paisley’s remarkable achievement of reaching this milestone four times as a country music superstar.

Unlike the Traveling Wilburys, this gritty, battle-worn outlaw-country supergroup lives up to its legendary reputation. Picture a Mount Rushmore of country greats—Kris Kristofferson, Waylon Jennings, Willie Nelson, and Johnny Cash—trading stories of their adventures around the world through song.

In a cosmic twist, it’s Johnny who ends up aboard a starship, soaring through the stars.

Though many covers have followed, it’s Williams’ original rendition that endures as a timeless classic. Interestingly, he first envisioned the song as spoken rather than sung. The heartfelt lyrics reflect the turmoil of Williams’ troubled marriage, and even Elvis once called it “probably the saddest song I’ve ever heard.”

Country legend George Strait delivers a standout hit with this infectious track, reflecting on past romances and explaining why a man might prefer life in Tennessee over the haunting memories of Texas.

The song has made its way onto numerous movie and video soundtracks—and even earned a shoutout from Drake in HYFR. When Drake name-drops you, that’s when you know you’ve really made it, right?

Although Don Schlitz’s lyrics have been recorded by multiple artists, it’s Rogers’ rendition that remains timeless. His smooth vocals bring the thoughtful lyrics to life, weaving a captivating tale of a chance encounter on a train and how life’s most meaningful moments often emerge from the simplest, most unexpected places.

Lucinda Williams’ rise to stardom may have been slow, but it was well worth the wait. Although her early albums in the late ’70s earned critical praise, mainstream success remained out of reach until her fifth release, Car Wheels on a Gravel Road, captivated listeners in 1998. Her reputation steadily grew during the long gaps between albums, and it’s easy to see why this one resonated so deeply.

The opening track, Right In Time, is a masterpiece—capturing the quiet nuances of domestic life with a touch of nostalgia, before swelling into a powerful chorus where memories of a past lover spring vividly to life.

Mary Ann and Wanda share a deep bond rooted in years of friendship, but their future is jeopardized by Wanda’s abusive husband. Together, they decide it’s time to “handle” the situation. The playful, sassy music video brings the story to life with an engaging cast, including a young Jane Krakowski and Dennis Franz.

Is Swift aware that Romeo and Juliet doesn’t exactly have a happy ending? Regardless, her fresh take on Shakespeare’s tale turned into a smash hit from the rising country star’s 2008 sophomore album. The song broke genre barriers, climbing beyond the country charts to dominate pop music.

While adult Taylor reimagined it in 2021, the original remains timeless—seamlessly blending youthful innocence with songwriting far beyond her years.

It’s astonishing to think this song was written and recorded all the way back in 1952. In her powerful rendition of J.D. Miller’s lyrics, Wells boldly argued that women’s infidelity often stemmed from the unfaithfulness of their men.

As a direct response to Hank Thompson’s The Wild Side of Life, the track sent shockwaves through the world of female country artists, marking a pivotal moment in the genre’s history.

Shania’s 90s takeover was so revolutionary, it’s easy to forget the storm she unleashed. Imagine a young Canadian with a golden voice, disrupting the country scene with bold charisma and glamour, all while breaking into MTV’s boy band-dominated lineup with fiddles and twang. She continues to rile up traditionalists, solidifying her place as an icon for country music’s rule-breakers. Then there’s Man! I Feel Like A Woman!—her masterpiece.

This high-energy, sexually charged anthem celebrates womanhood on its own terms. Unapologetically rebellious and still provocative, it remains as captivating as ever.

The fiery-haired alt-country queen would later find greater commercial success, but her third album, Blacklisted, stands as her magnum opus—a flawlessly crafted work of Lynchian country noir.

The standout track, Deep Red Bells, offers a chilling reflection on growing up in the Pacific Northwest amid the fear cast by the Green River Serial Killer. Case’s low, controlled wails resonate with eerie intensity, leaving a haunting impression that makes the song truly unforgettable.

Will Oldham—better known as Bonnie ‘Prince’ Billy—is the quintessential alt-country/indie folk (or however you choose to label him) artist. His most iconic recorded moment is the 1999 track I See A Darkness.

This somber piano dirge unfolds into a softly glowing country chorus, where he pleads for the strength of friendship to carry him through life’s darkest moments. Johnny Cash’s renowned cover on American III cemented it as a solemn modern classic.

Tanya Tucker burst onto the country music scene as a young sensation with her haunting rendition of Delta Dawn, a song about a mysterious woman. Although it had been recorded by others before, 13-year-old Tanya’s husky, mature voice resonated deeply with country fans, propelling the track into the Top 10.

Her distinctive interpretation captivated audiences and secured her spot in music history.

Hank Williams’ career may have been brief, but he made an indelible mark on country music, shaping the genre’s future and leaving behind a remarkable legacy. As one of the greatest songwriters in country history, he penned I Saw the Light, a soulful gospel tune that, despite not being an instant hit, gained traction over time and became the go-to finale for his live performances.

Like many of Hank’s timeless songs, it has been covered endlessly by artists who continue to find inspiration in his work.

Hank Williams’ gift for weaving heart, soul, and personal experience into his lyrics made this song a country music classic. Written for his ex-wife Audrey, it was released shortly after his death in January 1953, achieving massive posthumous success.

While many artists have covered it over the years, none capture the raw emotion quite like Hank, whose voice carries the weight of genuine heartbreak.