Following his arrest for kidnapping and aggravated robbery, he was sent to prison in 1988, serving 16 months of a four-year sentence. During his time in prison, Diaz would perform stand-up routines for his fellow inmates during the weekly film screening event when the projector broke. It took Diaz a further three years to try stand-up, despite being often told of his talent, and later called his entry into the line of work as "the last resort" as he had many other jobs in the past.
