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Born Jason DeFord, Jelly Roll began rapping around 2005, and started to break through the underground thanks to collaborations with Lil Wyte and Haystak. In 2011, he joined Wyte and BPZ in the group SNO, who issued Year Round, an album produced by DJ Paul and Juicy J and released on the Three 6 Mafia-associated label Hypnotize Minds. Jelly Roll's independent debut album, The Big Sal Story, appeared in 2012, and in 2013 he announced his Whiskey, Weed, & Waffle House mixtape, quickly drawing the attention of the breakfast restaurant chain's legal department. After a cease-and-desist letter from Waffle House, and some nasty online posts from Jelly Roll, the two parties settled their beef with the mixtape renamed Whiskey, Weed, & Women, while the rapper declared the chain was still his favorite. By the end of the year, he and Haystak released the collaborative album Business as Usual.
The solo album Biggest Loser followed in 2014, along with the EP Whiskey Sessions. Two years later, Jelly Roll was back with Sobriety Sucks, which featured Struggle on "Train Tracks" and Alexander King on "Need Nobody." The LP became his first to chart, hitting Top Heatseekers, Independent Albums, and even the R&B Albums chart. He followed with No Filter 2 at the end of 2016 before issuing Addiction Kills in April 2017. He teamed up with Struggle again on 2018's Waylon & Willie II & III; that same year, he released the solo Goodnight Nashville. In 2019, Jelly Roll issued a second Whiskey Sessions and the EP Crosses and Crossroads. In March 2020, he put out the full-length album A Beautiful Disaster, which featured guest spots by Krizz Kaliko, Lil Wyte, Struggle Jennings, and others. It landed at number nine on the Billboard Independent Albums chart. Another full-length, Self Medicated, followed that October.
In 2021, Jelly Roll offered up the short project Ballads of the Broken. The brief album took a different stylistic approach on almost every track, going from country-adjacent hooks to eerie, remorse-filled pop tunes. In addition to eight more fully fleshed-out productions, Ballads of the Broken included two demo recordings. The set broke into the Billboard 200 and the U.S. Indie Top 30. 2023 saw the release of Whitsitt Chapel, which included the hit single "Need a Favor." ~ David Jeffries