Webster Gradney, a.k.a. Webbie, was born on September 6, 1985, in Baton Rouge Louisiana. He lost his mother at a young age. Webbie, along with his brothers, was raised by his father, a plant operator who was unable to be home a lot due to his job. Webster spent a lot of time at his grandmother's house, along with his other cousins who all had a significant influence on his life.
When Webbie was twelve, he was turned onto hip hop after spending time with an older cousin who used to rap. He was intrigued and wanted to be down with rap too, so he and his older cousin started a group. Unfortunately it didn't last long because everyone realized that Webbie was a better rapper than his cousin, which soon led to tension in the group and eventually they broke up.
The group's breakup didn't stop the young rapper. One evening in the fall of 2001, a mutual friend of one of the founders of Trill Entertainment brought Webster over to Trill Studio where they let him freestyle to a track they were working on. It was all history after that: he rapped about his mom and the whole staff at the studio was blown away on how much passion this young rapper had. Soon after, Webbie made his debut on the album entitled Ghetto Stories along with Lil' Boosie. The album was independently released, selling over 15,000 units.