Wilson's start in wrestling came when she attended a World Championship Wrestling (WCW) show with her boyfriend in 1999. After going backstage, she was asked to walk out to the ring with Scott Steiner. Later, Kevin Nash expressed an interest in doing a storyline with her. She debuted as "Samantha" on the February 11, 1999 episode of Thunder. Wilson was brought in by the New World Order (nWo) to seduce David Flair into turning against his father, Ric Flair. They appeared together on February 21 at SuperBrawl IX when Wilson slapped Ric, and David zapped him with a taser. After Ric won the WCW World Heavyweight Championship from Hollywood Hogan at Uncensored inside a Barbed Wire Steel Cage match, David and Wilson took some time off from WCW television in April before returning in May to accompany David to the ring for matches. At the 1999 Bash at the Beach, Wilson acted as a valet for Flair as he successfully defended the WCW United States Heavyweight Championship against Dean Malenko.