Before his rapping career, Birklett was a successful drug dealer, who funded his music business with the money he earned from selling drugs. In 1988, he founded Short Stop Records and joined the group Mass 187 in 1995. Mass 187's song "Gangsta Strut" was featured on local radio. He eventually was convicted of "using a communications device to commit a felony" and was sentenced to eighteen months in prison, although served only nine months in Beaumont, Texas, federal detention.
Lil' Troy, who featured in his songs many members of Houston's thriving rap scene of the late 1990s, managed to reach national audiences with his single "Wanna Be a Baller" produced by Bruce "Grim" Rhodes. The song reached #70 on the Billboard Hot 100, and propelled his debut album, Sittin' Fat Down South, to the Top 25 albums on the Billboard 200. After the success of the lead single, Lil' Troy was picked up by Universal Music Group, which re-released his debut album in 1999 with a larger national distribution. The debut album was a success, as it certified platinum by the RIAA selling 1.9 million copies. Lil' Troy released his follow up in 2001, titled Back to Ballin. This album did not contain a charting single and did not fare nearly as well as his debut. He released his third and to date last album, Paperwork, in 2006.