At Wrestlemania XIX, Booker T competed against Triple H for the World Heavyweight Championship. This match was good, but not necessarily stellar. It's mostly remembered for the hilarious commentary from J.R. and The King, more specifically The King's constant riding on Booker. Highlights include wondering aloud if he's having flashbacks of being behind bars and reminiscing about the time they went shopping and Booker tried to pay for everything with cigarettes. A decent angle, and one that was rooted in fact, as Booker T once spent 19 months behind bars. Booker T was the youngest child of eight kids, raised by a single working mother in Houston, Texas. As he got older, he got a job in Wendys flipping burgers, but it was still a tough situation. With money being tight, he turned to crime, committing armed robberies on several chains of Wendys restaurants. By 1987, he and his partners were caught and he pleaded guilty. There wasn't much else he could do, to be honest. The familiarity with the running of store operations on behalf of the robbers suggested an inside job. And the fact that Booker and his buddies wore their Wendys uniforms while robbing Wendys restaurants was just overkill. Booker was sentenced to five years for aggravated robbery, and served just over a third of his term before being released. Not long after, he was a struggling single parent himself, working in a storage facility to support himself and his infant son and wishing for a better life. It was then that his elder brother Lash suggested pro wrestling. Lash, by the way, would later go on to be known as Stevie Ray, the other half of Harlem Heat. Booker borrowed a few grand from his boss to pay for wrestling classes, and the rest is history.