Key made his televised World Wrestling Federation (WWF) debut on the July 26, 1999 episode of Raw. He portrayed a drug dealer character along with Droz and Prince Albert and feuded with The Godfather. The Godfather suffered an injury just as the feud between the two was developing, leading to Key being taken off television.
The WWF soon sent Key to work for the Extreme Championship Wrestling (ECW) promotion to further develop his skills. There, Key, under his real name Vic Grimes, joined Tony DeVito and Spanish Angel, replacing P.N. News, in Da Baldies. The highlights of his ECW tenure were a fast-paced match against Kid Kash, an ECW World Heavyweight Title shot against Mike Awesome, and a Danbury Street Fight with Tommy Dreamer.
During Living Dangerously in March 2000, a breakdown in communication between New Jack and Grimes led to both men tumbling off a 20-foot high scaffolding rig onto concrete. Grimes departed ECW not long after this incident.