Roberts began watching wrestling, after he saw an edition of Saturday Night's Main Event. and met Kerry Von Erich and The Ultimate Warrior at a hotel in Wisconsin. The combined events inspired Roberts to become a fan of professional wrestling. He also briefly trained as a referee so he could be in the same ring as Curt Hennig, of whom he was a big fan.
Roberts began ring announcing at age 16 for local professional wrestling promotion Pro Wrestling International, and announced his first match in November 1996. He then worked for other independent promotions such as the American Wrestling Alliance (AWA) and Impact Zone Wrestling while studying Media Arts and Communications at the University of Arizona from 1998 to 2002. During this time, he also announced for the Toughman Contest. In 2002, Roberts was hired by World Wrestling Entertainment as a backup announcer for SmackDown, followed later by a move to the Raw brand. He also worked on Velocity and Heat shows while touring as the full time Raw live event announcer. Most notably, Roberts announced the ECW show each week on the Sci Fi Network until September 2007 before swapping with SmackDown's Tony Chimel. Roberts reached the peak of his profession when he announced the main event of WrestleMania XXIV between Edge and The Undertaker on March 30, 2008. In addition to announcing on SmackDown and SmackDown pay-per-view matches Roberts would also announce on WWE Superstars starting on the inaugural episode on April 16, 2009 episode.
Beginning on September 28, 2009, Roberts took over the Raw announcing duties from the departing Lilian Garcia. After his departure from SmackDown, Tony Chimel returned to SmackDown to take over Roberts' duties on October 2.