In late 1992, Dudley joined Extreme Championship Wrestling, where he adopted the ring name E.Z. Ryder and formed a tag team known as "The Hell Riders" with H.D. Ryder. On the inaugural episode of ECW Hardcore TV (airing April 3, 1993), The Hell Riders unsuccessfully challenged The Super Destroyers for the ECW Tag Team Championship. He left ECW in late 1993.
In mid-1995, he returned to Extreme Championship Wrestling. He was given the gimmick of Chubby Dudley, an obese, slobbish member of the Dudley family. Chubby rarely wrestled, but would accompany his storyline half-brothers to ringside, normally while holding a cake or other snack. If the other members of the Dudley family were incapacitated, Chubby would flee from ringside.
At "Massacre on Queens Blvd" on April 13, 1996, D-Von Dudley made his debut, angrily proclaiming that the Dudley's comedic antics were not the way "true Dudleys" should conduct themselves. At Heat Wave on July 13, 1996, D-Von attacked Dances with Dudley, Chubby Dudley and Sign Guy Dudley with a chair and delivered a low blow to Buh Buh Ray before being driven off by Hack Meyers.
Dudley left ECW again in mid-1996.