She debuted in World Championship Wrestling (WCW) 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.
She continued to accompany David to the ring until September when David was on the telephone with Wilson and later found out that Wilson was in the Filthy Animals' locker room flirting with Billy Kidman, which resulted in a feud between Flair and Kidman. On the October 18, 1999 episode of Nitro, Wilson turned on him, resulting in Flair losing the match and the Animals beating on him; after the Animals stopped assaulting David, Wilson left with the Filthy Animals. It was around this time that Wilson began managing Kidman and his Filthy Animals teammates. As a result, she found herself involved in the Animals continuing feud with The Revolution. On the November 22, 1999 episode of Nitro, during a tag team match between Kidman and Konnan facing Creative Control for the WCW World Tag Team Championship, Kidman looked up at the Turnertron and saw that Wilson and Eddie Guerrero were shown flirting inside his locker room on the "Kidcam", a hidden camera segment, which led to a storyline feud between Kidman and Guerrero. Following this, Wilson once again disappeared from television. Wilson however returned on the January 19, 2000 episode of Thunder managing Kidman, and in April 2000, Kidman and Wilson joined a stable known as the New Blood, making them both villainous characters. As part of their newest storyline, Kidman became jealous of the attention Wilson began to give to fellow New Blood member Horace Hogan. In June, Wilson gave Kidman a hit at the Great American Bash, causing him to lose to Horace's uncle, Hulk Hogan.
Wilson was taken off of television following the encounter, reappearing at July's Bash at the Beach during a match between Shane Douglas and Buff Bagwell. After the match, Wilson and Douglas left together, which led to a feud between Kidman and Douglas. At September's Fall Brawl, Wilson and Douglas defeated Kidman and Madusa in a mixed tag team match with scaffolding erected above the ring. Wilson was released from WCW in December 2000.
Wilson made her World Wrestling Federation (WWF) television debut as a heel on the June 28, 2001 episode of SmackDown! as part of The Alliance during the Invasion angle in 2001. In her first storyline with the company, she portrayed Vince McMahon's latest affair. She also regularly teamed with fellow WCW performer Stacy Keibler. The duo made their wrestling debuts in a Bra and Panties match against Lita and Trish Stratus at the InVasion pay-per-view, which Stratus and Lita won by stripping Keibler and Wilson to their yellow and white bikinis. The following night on Raw, Wilson defeated Stratus in a Paddle on a Pole match. Despite her relative lack of in-ring experience, Wilson, alongside Keibler and Ivory, regularly feuded with the Divas, as well as interfering in matches on behalf of other wrestlers in The Alliance.
She became a face during the Invasion storyline when her character began an on-screen romance with Tajiri. This new romance caused the evil Stacy Keibler to turn against Wilson, and as a result of this, Wilson defected to the WWF. Wilson defeated Keibler in the first ever lingerie match at No Mercy. When the first ever brand separation of the company roster took place in March 2002, Wilson was drafted to SmackDown!. Shortly after this, as part of the storyline, Tajiri soon became jealous over the increased attention that Wilson received from other men, so he forced her to wear a geisha outfit, and he also appeared to mistreat her in matches. She depantsed Rico on the April 25, 2002 edition of SmackDown!. Wilson finally grew tired of this, and during Tajiri's match against The Hurricane, she got on top of the announcer's table and stripped off her clothing. The distraction allowed The Hurricane to pick up the win. At Rebellion, Wilson and Billy Kidman defeated John Cena and Dawn Marie in an intergender tag team match. After the match, Wilson and Kidman kissed. Wilson then got her first WWE Women's Championship match on SmackDown! after Women's Champion Molly Holly invaded the show interrupting Wilson's photoshoot and challenging her to a match in which Wilson was unsuccessful in winning.
Wilson started a controversial feud with Dawn Marie in September 2002, in which Dawn would start a relationship with Wilson's real-life father Al Wilson. On the October 17 episode of SmackDown!, Wilson teamed up with Rikishi in a losing effort to the team of Dawn and Matt Hardy. In response, Wilson defeated Dawn at No Mercy in October. Soon afterwards, Dawn would get engaged to Al, and told Wilson that she would break it off if she spent a night in a hotel room with her, though Dawn would later reveal this was a lie. Dawn would eventually show footage of this at Armageddon. The feud continued into 2003 when Dawn and Al got married on the January 2 episode of SmackDown! in their underwear. One week later, Al then, in storyline, died from a heart attack after having rigorous sex numerous times in succession on their honeymoon. Wilson defeated Dawn again to end the feud at the Royal Rumble in what was billed as a Stepmother vs. Stepdaughter match.
In May 2003, Wilson appeared in a pictorial and on the cover of Playboy magazine. A few months earlier, when her pictorial was announced, a short storyline feud with Nidia developed, with the latter being jealous of the fact that Wilson was chosen for the cover and spread in the magazine. In weekly vignettes aired on SmackDown!, both Nidia and her on-screen boyfriend Jamie Noble made trips to The Playboy Mansion to complain to Hugh Hefner over his choice. On the SmackDown! after WrestleMania XIX, during a segment labeled as Wilson's Playboy Coming Out Party former Diva and Playboy covergirl Sable made her return to WWE after a four-year absence. This began a storyline between the two women where for weeks, Sable played mind games with Wilson, being friendly one moment and unfriendly the next. This all led up to a bikini contest between the two at Judgment Day, which Wilson won. Continuing her feud with Noble and Nidia from earlier in the year, Wilson managed Billy Gunn upon his WWE return in the summer of 2003. The feud came to an end after Nidia and Noble both became fan favorites and sided with Gunn and Wilson. After the formation of this alliance, Wilson, Nidia, and Dawn Marie feuded with Shaniqua for a short period of time, which led to Shaniqua physically dominating Wilson and Nidia in a handicap match.
Wilson teamed with Sable in March 2004 to feud with Raw Divas Stacy Keibler and Miss Jackie. The feud's storyline centered on the latter duo's jealousy of Wilson and Sable as Playboy cover girls, as well as their recently being named cover girls yet again, as the two Divas were announced to be featured together in an upcoming Playboy March 2004 issue. After weeks of rivalry, Wilson and Sable defeated Keibler and Miss Jackie in a Playboy Evening Gown match at WrestleMania XX by stripping their opponents of their evening gowns. Wilson also wrestled Rene Dupree to a draw on the April 29 edition of SmackDown. In May, Wilson began a second feud with Dawn Marie again. As part of the feud, the two had a match with Wilson's career on the line when the SmackDown! General Manager at the time, Kurt Angle, made the stipulation for the match at Judgment Day, which Wilson defeated Dawn to keep her career. Later in the year, Wilson engaged in a short feud with Sable, who defeated her at The Great American Bash. On the July 1 edition of SmackDown, Sable was defeated by Wilson in a rematch. In November, Wilson began feuding with Hiroko. On the December 2 episode of SmackDown!, Wilson teamed up with Rey Mysterio and Rob Van Dam in a winning effort against Hiroko, Kenzo Suzuki and Rene Dupree.
On February 10, 2005, on a special episode of SmackDown! (recorded on February 4 in Saitama, Japan), Torrie defeated Hiroko in a kimono match by removing her kimono first. Torrie was then involved in a short-lived feud with MNM valet Melina. On July 24 at The Great American Bash, the two of them faced in a bra and panties match with Candice Michelle as the special guest referee, in which Wilson was defeated. A rematch between both of them took place on the July 28 episode of SmackDown!, where Melina was once again victorious.
It was revealed on August 22, 2005 that Wilson and Candice Michelle had been moved to the Raw brand as a part of a trade in exchange for Stacy Keibler and Christy Hemme. On that night, Wilson and Candice turned heel by attacking 2005 Diva Search winner Ashley Massaro. Her and Candice's storyline feud with Massaro continued over the next couple weeks, as the duo, along with their enforcer Victoria (dubbed as the "Skankateers" by Trish Stratus), made things difficult for Massaro. On the September 5 episode of Raw, Wilson defeated Massaro after interference from Victoria and Candice. Massaro evened the score on the September 12, 2005 episode of Raw when she brought out the returning Stratus, and the duo proceeded to attack the heels. Later that night, Wilson teamed up with Victoria in a losing effort to Stratus and Massaro. This led to a tag team match at Unforgiven, where the team of Stratus and Massaro defeated Wilson and Victoria. The following night on Raw, Wilson was defeated by Stratus. After the match, Wilson, Victoria and Candice attacked Massaro and Stratus. The feud continued into WWE Homecoming, where Stratus and Massaro defeated Wilson, Candice, and Victoria in the first ever three on two Bra and Panties match by stripping all three of their opponents.
Wilson was absent from WWE television for quite some time after this, leading to rumors and false reports that she had been released from WWE.
On October 17, Wilson made her return to Raw, where she, Candice and Victoria faced off against the team of Stratus, Massaro, and their new ally Mickie James in a winning effort after Wilson pinned James. On the November 28 episode of Raw, Wilson teamed up with Victoria and Candice Michelle in losing effort to Stratus, Massaro and James. On the February 13, 2006 episode of Raw, Wilson was accompanied by Candice in a losing effort to Massaro. Wilson soon turned face once again, after Candice and Victoria both turned against her. On the March 13 episode of Raw, Wilson helped Stratus retain the Women's Championship against Victoria who was accompanied by Candice. The following week on Raw, Wilson teamed up with Stratus to defeat Victoria and Candice. The storyline feud between Candice and Wilson led to a match where Wilson faced Playboy's newest cover girl, Candice, at WrestleMania 22 in a Playboy Pillow Fight. Wilson won the match, but the feud still continued on-and-off for some time. On the June 12, 2006 episode of Raw, Wilson defeated Candice in the first ever "Wet and Wild match", a wrestling match involving water balloons and squirt guns, in which the winner of the match would be on the cover of the WWE 2006 Summer Special magazine.
Wilson also made a special appearance on WWE's ECW brand on August 22, 2006 representing Raw in a bikini contest against ECW Diva Kelly Kelly. A winner was not decided, however, and a six-person mixed tag match began pitting Wilson, Tommy Dreamer, and The Sandman against the team of Kelly Kelly, Mike Knox, and Test. Wilson's team was victorious.
In the final months of 2006, Wilson entered into an on-screen relationship with Carlito. On the November 27 episode of Raw, Wilson participated in a #1 Contenders Diva Battle Royal that was won by Victoria. On the December 11 episode of Raw, Wilson was defeated by Victoria and after the match Chris Masters proceeded to put Wilson in a Masterlock until she was saved by Carlito. During this time, Ric Flair took an interest in Carlito, and Wilson accompanied the duo in a series of tag matches. On the March 12 episode of Raw, Wilson was defeated by then Women's Champion Melina; after the match Melina attacked Wilson but was stopped by Mickie James, who was then stopped by Victoria, Melina then attempted to escape but was stopped by Ashley Massaro. In May 2007, however, Carlito turned against Flair and dumped Wilson when he became a heel. For laughing at Vince McMahon, he decided to put her in a match with Carlito, in which she lost on the June 4, 2007 episode of Raw.
The storyline came to a halt when on the June 11 episode of Raw, Wilson was drafted from Raw to SmackDown! as part of the 2007 WWE Draft. As she returned, she acted as a valet for Jimmy Wang Yang and the duo was placed in feuds against Victoria and Kenny Dykstra.
At SummerSlam, Wilson participated in a number one contenders Battle Royal which was won by Beth Phoenix. On the September 21 episode of SmackDown!, Wilson was one of the bridesmaids at the Theodore Long - Kristal Marshall wedding. On the September 28 episode of SmackDown!, after losing to Victoria, she was attacked in the ring by the debuting villainess Krissy Vaine, but the feud was prematurely dropped when Vaine left the company. On the October 29 episode of Raw, Wilson competed in the Halloween Divas Battle Royal eliminating Victoria before being last eliminated by Kelly Kelly, who defeated her with a strike to the groin. On the November 16 episode of SmackDown!, Wilson teamed up with Mickie James in a losing effort to Phoenix and Victoria. She was on James's team at Survivor Series, which was victorious over Phoenix's. Wilson's last appearance was on the November 23 episode of SmackDown!, defeating long-time rival Victoria. In November, Wilson took time off from wrestling to undergo physical therapy in relation to a previous back injury. On May 8, 2008, Wilson was released from her WWE contract and she subsequently retired.
Eleven months after her release, Wilson returned on April 5, 2009, at WrestleMania XXV, competing in the 25-Diva Royal to crown Miss WrestleMania, which was won by Santina Marella. Wilson was shown in the audience at WrestleMania XXVIII.
On the January 22, 2018, episode of Raw, Wilson was honored being "one of the greatest female superstars in the history of WWE" and made a special appearance as part of the 25th anniversary of Raw along with fellow wrestlers and former co-workers; The Bella Twins, Maryse, Kelly Kelly, Lilian Garcia, Michelle McCool, Terri Runnels, Maria Kanellis, and Hall of Famers Trish Stratus and Jacqueline. On January 28 at the Royal Rumble, Wilson made a surprise entrance at number 9 during the first women's Royal Rumble match, in which she eliminated Dana Brooke before ultimately being eliminated by Sonya Deville. On October, 28, Wilson took part on a Battle Royal during the first ever all women's pay–per–view Evolution, in which the winner would receive a future WWE Women’s Championship match, but was unsuccessful as she was eliminated by Mandy Rose.
On March 4, 2019, it was announced that Wilson would be inducted into the WWE Hall of Fame class of 2019. At the ceremony on April 6, she was inducted by Stacy Keibler. The next night at WrestleMania 35, she appeared during transmission while she was introduced as part of the 2019 Hall of Fame class.