Jelly Roll is one of the hottest artists in country music today. However, he hasn’t always been a country singer. The Antioch, Tennessee native walked a long and beautifully broken road to stardom. He started his career as an underground hip-hop artist before beginning his transition away from the genre in the late 2010s. He moved through rock before landing in the country genre with last year’s Whitsitt Chapel.
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He has seen many career milestones in the last two years with Grammy nominations, No. 1 songs, hit albums, and wins at multiple country music awards shows. Today (December 4) sees him celebrating a personal milestone. It’s his 40th birthday. To celebrate, we’re going to look at four songs that led him to country stardom.
“10 Minute Freestyle”
You’re not going to find this one on your favorite streaming platform. Instead, you’ll have to go to YouTube to see a young Jelly Roll, fresh out of jail, laying down a 10-minute freestyle rap. This is nothing like what new fans are used to hearing from him. However, those who have been following his career since the early days are well-acquainted with the video.
This clip didn’t just garner notoriety for the up-and-comer, it also spawned an early catchphrase that found its way onto t-shirts and other merchandise—“If my P.O. asks, I hang drywall.”
“On My Way” Featuring Joey Mac
Gamblin’ on a White Boy 4 was the long-awaited final installment of Jelly Roll’s Gamblin’ on a White Boy mixtape series. It dropped in June 2011 and featured some of his best work to date. Again, this is not what newer fans are used to hearing from the “Save Me” singer. However, it shows that he was ambitious long before he stepped into the country music world and found acclaim and success.
“Sunday Morning”
Jelly Roll started showing signs of getting away from hip-hop with his Whiskey Sessions albums. The first installment isn’t available on streaming platforms. However, Whiskey Sessions II is available to stream everywhere. The 2019 outing gave listeners a look at the singer/songwriter’s future.
“Sunday Morning” was a standout track from that collection. It featured country-leaning production and showcased Jelly’s singing as well as his rapping.
“Son of a Sinner”
Before Jelly Roll committed to country music with Whitsitt Chapel in 2023, he released Ballads of the Broken in 2021. The rock-leaning album primed listeners for what was to come. It also featured his first country hit. “Son of a Sinner” went to No. 1 on the Billboard Country Airplay chart and officially started his journey to country music stardom.
Featured Image by Terry Wyatt/Getty Images
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