HomeEntertainmentMusicCountry MusicJelly Roll Just Landed His First Number 1 Single, Hear the 10-Minute Freestyle That Started It All

Jelly Roll Just Landed His First Number 1 Single, Hear the 10-Minute Freestyle That Started It All

by Clayton Edwards
Jelly Roll performs a sold-out show at Bridgestone Arena
(Photo by John Shearer/Getty Images for Jelly Roll)

Recently, Jelly Roll reached another major milestone in his career. He had already played the Grand Ole Opry a couple of times and sold out Bridgestone Arena. Now, his song “Son of a Sinner” topped the Billboard Country Airplay chart. “Son of a Sinner” was Jelly’s first entry on the country chart. However, he is far from new to the music world. In fact, the Nashville native has been working day and night to make his dream come true for more than a decade.

This long, slow climb is part of the reason that this chart-topper is such a big deal for Jelly Roll. “There is no greater reward for a singer and songwriter in Nashville, Tennessee than to have the #1 song on country radio,” he wrote in a Facebook post Sunday morning. “Now imagine that happening to a guy that grew up in this town … a guy that, at every turn in the last 25 years of his life, made the wrong decision. Imagine everyone telling that guy he had no chance at country radio. ‘You’re too overweight, you have too many tattoos, they will never let a convicted criminal on country radio.’ Now, imagine country radio proving everyone wrong and taking a chance on the song, the message, and the man.”

Jelly Roll added, “If you can imagine that, then you can [understand] why I’m so filled with gratitude as tears stream down my face while I type this, I have the number 1 song on country radio.”

The 10-Minute Freestyle That Put Jelly Roll on the Map

Jelly Roll co-penned “Son of a Sinner” with his longtime friend and collaborator David Ray and country up-and-comer ERNEST. However, no one wrote the verses that put the Pride of Antioch on the map. Instead, the rhymes flowed from Jelly’s mind like a faucet.

On January 29th, 2009, Jelly Roll had just gotten out of jail. Several of his good friends threw him a welcome home party. During that little shindig, Jelly started freestyling. Luckily, Chad Armes – another Nashville rapper – was there to capture the whole thing on video. Check out the 10-minute NSFW video below.

In the freestyle, Jelly Roll talks about his incarceration, drug dealing, and gang affiliation. At the time, he was still living within those “wrong decisions” he mentioned in his recent Facebook post. More than that, it was the video that put him on the map. In 2010, he appeared on the song “Pop Another Pill” with Memphis-based rapped Lil’ Wyte.

After that, Jelly Roll found himself collaborating with some of the biggest names in independent hip hop. He appeared on mixtapes, albums, and songs with Haystak, Alexander King (Lexx Luger), Tech N9ne, and more. Additionally, Jelly released a stack of mixtapes, EPs, and albums.

These days, Jelly Roll is a family man who seems finished with those “wrong decisions” with a chart-topping single. However, anyone who has followed his career from the beginning knows that Jelly is a success story and an inspiration for anyone who is living in the trenches and trying to make it to the top.