Roberts is best known for his two stints in the World Wrestling Federation (later called WWE); the first between 1986 and 1992, and the second between 1996 and 1997. He wrestled in the National Wrestling Alliance in 1983, World Championship Wrestling in 1992, and the Mexico-based Asistencia Asesoría y Administración between 1993 and 1994 and again in 1997. He appeared in Extreme Championship Wrestling during the summer of 1997 and made appearances for Total Nonstop Action Wrestling from 2006 through 2008.

Throughout his career he was known for his intense and cerebral promos, his dark charisma, his extensive use of psychology in his matches and his use of the DDT finishing move, which was named the "coolest" maneuver of all time by WWE. He often brought snakes into the ring, most famously a python named Damien. Roberts was also one of the subjects of the 1999 documentary film Beyond the Mat. In 2012, Roberts moved in with fellow wrestler Diamond Dallas Page to seek help in getting his life back on track following years of alcohol and drug abuse. He was inducted into the WWE Hall of Fame on April 5, 2014.