Although Houston rapper Wine-O's debut single, "Pop My Trunk," featuring Paul Wall, may have been booming from car stereos in 2005, he was not a rookie. During the late '90s and early 2000s, Wine-O was a well-respected and prolific Christian rap artist in Texas under the pseudonym Nuwine. Born and raised Maurice Williams in Houston's poverty-stricken Fifth Ward, he spent most of his youth in and out of jail, selling drugs, and stealing automobiles. His precarious, crime-laden lifestyle came to a climax when he was shot at a convenience store — the bullet entered through his cheek and exited between his eyes, necessitating that he be airlifted to the hospital. Notwithstanding incredible odds, Williams survived. Nevertheless, it took another impending crisis — a possible 15-year prison sentence for another offense — before he found salvation in Christianity.
With a hard-edged swagger reminiscent of his prior life, Williams produced and released his brand of gospel rap under the Nuwine moniker. He refused to be labeled as Christian rap — preferring "spiritual rap" — in order to reach a broader audience. Strong indicators of his success and mission were marked by his independently released album Ghetto Mission, attaining spots on both the Top R&B/Hip-Hop and Top Contemporary Christian album charts in 2000 and also his hosting of a local TV show of the same name. Having produced tracks for Mike Jones and Letoya Luckett, Williams began entering the secular pop music world and, as Wine-O, released the Houston anthem "Pop My Trunk." The song settled in the Top 100 of the R&B/Hip-Hop singles chart for several weeks, landing him a distribution deal with Universal Music Group in July 2006. His major-label debut, Hate Me, was slated for October later that year, but label woes kept the album off shelves for an indefinite amount of time. Within a few years, he was going by Hefe Wine.