Booker was born the youngest of eight children, in Plain Dealing, Louisiana, though his birthplace is often misidentified as Houston, Texas. By the time Booker was 13, both of his parents had died and he lived with his 16-year-old sister. He would move in with his older brother Lash "Stevie Ray" Huffman at age 17. In high school, Booker was a drum major. He also played football and basketball.
Booker spent nineteen months in prison after pleading guilty to armed robberies at Wendy's restaurants in Houston. Booker and his partners wore Wendy's uniforms during the holdups since they had been working there for 2½ years. Because of the gunmen's uniforms and familiarity with the fast food chain's operations, police suspected the robberies were inside jobs—and it did not take long before Huffman and three other men were found. Booker pleaded guilty in December 1987 to two aggravated robbery counts and was sentenced to five years in prison. He was released after serving 19 months, and was placed on parole until April 1992.