Siddiq was born in Houston. After his parents' separation, Siddiq and his siblings were raised by their single mother, living for a time in the projects. He and his siblings also went on to live with other family members. Siddiq started selling drugs around the age of 14 and was imprisoned at the age of 19 for trafficking in cocaine. He served 6 years of a 15 year sentence in the Ruben M. Torres Unit in Hondo, Texas. It was during his incarceration, while telling jokes to fellow inmates, that he discovered his ability to make people laugh. He worked in the prison's laundromat and his workmates were his captive audience.

After his release from prison in 1997, Siddiq started doing stand-up at the Just Joking Comedy Cafe in Houston. His first stage appearance was during the comedy club's Apollo Night, which tended to attract a college crowd. Siddiq was booed on his first occasion on stage because he was wearing a suit. He decided to wait a couple of weeks before trying again while wearing jeans and a t-shirt. Siddiq became the co-host of the Apollo Night show a month later.