Nashville, Tennessee, is known for its towering icons—names like Dolly Parton, Johnny Cash, and Reba McEntire. These legends helped build Music City’s reputation as the heart of country music and beyond. However, for every legend, there are dozens of artists who have faced long struggles, setbacks, and hustle before they could claim their place in the spotlight.
Music City is often called a “five-year town” because it takes that long—sometimes longer—for an artist to truly get noticed or respected by big labels. But the story of Nashville’s underdogs, those artists who rise from humble beginnings, is just as captivating as the legends who have walked before them. In this blog, we’ll explore some of Nashville’s modern-day underdogs and the journey they’ve taken to get to where they are today.
Dolly Parton: The Queen Who Rose from Nothing
Before Dolly Parton became the Queen of Country, she was a young girl from the Appalachian Mountains of Tennessee, growing up in a one-room cabin with 11 siblings. Music was always her passion, but the road to success was far from easy. Dolly moved to Nashville at the age of 18 with little more than her suitcase and dreams of making it big in country music. Despite her undeniable talent, she faced rejection after rejection, often told that she didn’t fit the “Nashville Sound” that was popular at the time.
But Dolly didn’t give up. She started performing on local radio stations and TV shows, using her charisma and unique voice to win over fans. Slowly but surely, Dolly began to build her fanbase, and in 1967, she got a break as a songwriter when Billie Jean recorded “Dumb Blonde,” which helped her secure a recording contract. By the time she released “Jolene” in 1973, Dolly’s sound was undeniable, and she became one of the most successful female country artists of all time.
Dolly’s story is a testament to the resilience it takes to make it in Nashville. Her rise from a struggling unknown to one of the biggest names in country music proves that Nashville is indeed a “five-year town”—a place where dreams are earned through hard work, dedication, and a relentless belief in one’s self.
Jelly Roll: The Rapper Who Found a Home in Country Music
Another perfect example of an underdog story in Nashville is Jelly Roll, an artist who defies the typical country music mold. Born Jason DeFord, Jelly Roll grew up in Nashville with a tough upbringing, facing challenges like substance abuse and legal issues. But despite the odds, Jelly Roll found his way to a career in music that blends elements of rap, country, and rock—a fusion that has drawn attention and admiration from both genres.
Jelly Roll’s rise to fame has been anything but conventional. He started out in Nashville’s underground rap scene, but his gritty lyrics and raw honesty quickly caught the attention of fans beyond hip-hop. He began blending his love of country music with his rap roots, and the result was a sound that felt uniquely Nashville—familiar yet fresh, honest, and vulnerable.
For years, Jelly Roll hustled, putting out independent albums and building a following through social media and live shows. In 2020, he began to gain wider recognition with his collaboration with Struggle Jennings on their album Waylon & Willie, which had country elements and reached listeners across both genres. His lyrics about real-life struggles, overcoming addiction, and redemption struck a chord with people, particularly in the South.
As he continued to make music, Jelly Roll found himself crossing over from the rap scene to country music, eventually securing a deal with Broken Bow Records. His success speaks to the changing landscape of Nashville—a place where artists are encouraged to bring their own unique blend of sound, no matter what genre they belong to. Jelly Roll’s hustle, grit, and unwavering determination to carve his own path are a perfect example of the underdog story in Music City.
The Five-Year Hustle: A Reality for Every Artist
In Nashville, they say it’s a “five-year town,” meaning it often takes at least five years of hard work, networking, and personal growth for an artist to earn respect from the big labels or break into mainstream success. The path to stardom in Nashville is rarely a straight line, and artists must often go through periods of struggle, rejection, and self-doubt before their talent gets the recognition it deserves.
For artists like Dolly Parton and Jelly Roll, those early years weren’t easy. They faced hardships, rejection, and discouragement, but they didn’t quit. They kept pushing, honing their craft, building relationships, and staying true to their art. In many ways, Nashville is a proving ground where artists must pay their dues before they can claim their place in the limelight.
The city’s vibrant music scene is part of what makes Nashville so special. It’s a place where the underdogs have the chance to showcase their talents and connect with an audience that appreciates authenticity and hard work. It’s not just the big names that make Nashville great—it’s the countless artists working behind the scenes, playing at small venues, writing songs, and doing whatever it takes to break through. They are the lifeblood of the city’s music scene, and they often inspire the next generation of artists to keep hustling and stay hopeful.
Nashville Experience Tours: Walk in the Footsteps of the Underdogs
If you’re ready to dive deeper into Nashville’s music history and see firsthand where the underdogs made their mark, join us for our Music Row Van Tour. On this exclusive tour, you’ll visit the legendary streets of Music Row, where artists from Dolly Parton to Jelly Roll honed their craft and created some of the biggest hits in music history.
Along the way, you’ll get the chance to see the iconic recording studios, songwriting hubs, and historic venues that helped shape the Nashville sound. You’ll also hear stories about the underdogs who made it big—the artists who started with little more than a dream, the ones who overcame obstacles to create some of the most iconic songs ever written.
Our tour is designed to give you a behind-the-scenes look at the hustle and heart of Nashville’s music scene. We’ll show you the places where legends have recorded their music, and where emerging stars continue to write their own stories.
Join the Journey of the Underdogs
Nashville is more than just a city—it’s a place where dreams come true for the underdogs. Whether they’re from small towns or big cities, country or hip-hop, the artists who succeed in Nashville are the ones who never give up. They keep grinding, working, and perfecting their craft, even when it seems impossible. At Nashville Experience Tours, we celebrate those stories, and we’re honored to share them with you.
So, grab your boots, book your spot on the Music Row Van Tour, and join us as we explore the hustle, the heart, and the history of Nashville’s music scene—where the underdogs become the legends.
Book your tour today and take the first step in walking through the history of Nashville’s music industry! 🎶
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