Webbie was born as Webster Gradney, Jr. in Houston, Texas but moved to Baton Rouge, Louisiana. His mother Joycelyn died of cancer when he was eight years old, so his parental care was split between his father and grandmother. Ever since he was five years old, he had been writing rhymes, and throughout his childhood he had become an avid fan of hardcore rap artists including Southern hip hop performers Master P, Eightball & MJG, the Geto Boys, and UGK, as well as West Coast rap such as 2Pac, Eazy-E, and Snoop Dogg. His admiration for hip-hop is attributed to his cousin from California. He attended Broadmoor Middle School, where he played fullback for the football team the Buccaneers. 7th grade math teacher Sean Fluharty described Gradney as a "quiet, mild-mannered student" and said "he was actually pretty good at math."
Under Trill, he recorded two albums in collaboration with fellow Baton Rouge-based rapper Lil' Boosie, Ghetto Stories in 2003 and Gangsta Musik in 2004. As Webbie's solo tracks "Gimme Dat" " were frequently featured in mixtapes, Trill began a deal to sign Webbie to the Warner Bros. Records subsidiary label Atlantic Records. He was signed there, and his major-label debut Savage Life was released in 2005, debuting at number eight on the Billboard Hot 100 chart. In 2007, he wrote and performed on the track "Wipe Me Down" by rapper and began work on his follow-up album Savage Life 2 which was released February 26, 2008. It debuted at number four on the Billboard Hot 100, selling 72,000 copies its debut week. Singles from Savage Life 2 include "Independent"