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Jackie Crockett of the National Wrestling Alliance first tried to convince Killings to become a professional wrestler, but he was determined to focus on his music career. Killings spent two years working on his music career and then contacted Crockett once more and expressed an interest in becoming a wrestler. Crockett, by now the senior cameraman for World Championship Wrestling, took Killings to several WCW and Pro Wrestling Federation events, introducing him to wrestling personalities.
Killings debuted in the PWF in 1997 as a manager, then spent three years traveling and training with Manny Fernandez. In 1999, he debuted in NWA Wildside as K-Krush, where he was awarded the newly-created NWA Wildside Television Championship on December 12. Killings lost the title to A.J. Styles on January 8, 2000.
At the urging of Rick Michaels, Killings sent a promotional videotape to the World Wrestling Federation. He was signed to a two-year developmental contract in 1999 and was assigned to Memphis Championship Wrestling, a WWF developmental territory. On April 12 in Robinsonville, Mississippi, he won a battle royal to claim the vacant Southern Heavyweight Championship. He lost the title to a masked Jerry Lawler on May 24 in Tunica, Mississippi, but reclaimed it from Joey Abs several months later in Memphis, Tennessee on August 19. His second reign ended on November 3, when he lost to Steve Bradley in Manila, Arkansas.
Killings was then promoted to the main roster and put in a tag team with Road Dogg. He debuted on the November 13, 2000 episode of Raw is War, attacking William Regal during a match against Road Dogg. Killings and the Road Dogg began rapping together, performing a song called "Gettin' Rowdy" as they approached the ring. Upon the return of Road Dogg's former partner Billy Gunn later that month, Killings was involved in a D-Generation X quasi-reunion. At Survivor Series, Killings teamed with former DX members Road Dogg, Billy Gunn, and Chyna to face The Radicalz in a Survivor Series match. Killings was eliminated and the Radicalz went on to win the match. At Armageddon, Killings and the Road Dogg took part in a four-way tag team match for the Tag Team Championship, which was won by Edge and Christian.
After Road Dogg was suspended in December and eventually released on January 26, 2001, Killings became a singles competitor and became a successful mainstay on Jakked. He took part in the 2001 Royal Rumble, but was eliminated by Big Show. Killings then began competing in the hardcore division. He defeated Raven for the Hardcore Championship on February 3, but lost the title to Crash Holly that same evening under the title's 24/7 rules. He defeated Raven for the title a second time on February 5, but once again he lost the title to Holly within the space of several hours. Killings became somewhat of a background figure of "The Invasion" angle during the summer months, often seen in dressing rooms and watching television with other superstars during inter-promotional matches. Killings was released from the WWF the next year.
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