Debra first appeared in World Championship Wrestling (WCW) in late-1995 and early-1996, making occasional unnamed appearances as an audience plant, and as part of a group of valets for the team of Hulk Hogan and "Macho Man" Randy Savage. In April 1996, she began appearing regularly as a valet for her husband, Steve "Mongo" McMichael as he transitioned from commentator to wrestler. Debra took on the role of a beauty-pageant queen character, giving herself the nickname "The Queen of WCW" and often making remarks about other wrestlers and valets in interviews.
At The Great American Bash 1996, Steve McMichael and his partner Kevin Greene competed against two of the Four Horsemen (Ric Flair and Arn Anderson). Flair won the match after Mongo and Debra turned on Greene by hitting him with a steel briefcase, joining the Four Horsemen. She managed the stable with Miss Elizabeth and Woman. The briefcase later became one of Debra's signature objects. At Bash at the Beach in July 1997, Debra turned on Mongo during his WCW United States Heavyweight Championship match against Jeff Jarrett by handing Jarrett the steel briefcase, which he then used to knock Mongo out and thus to win the match. Next, Debra briefly managed Goldberg and Alex Wright. On the November 24, 1997 edition of Nitro, Wright fired Debra after she accidentally distracted him, causing a loss to Prince Iaukea. After her divorce from McMichael, Debra left WCW.
In October of 1998, Debra rejoined Jarrett in the World Wrestling Federation (WWF). At the beginning of her WWF career, known as Debra McMichael and later simply as Debra, she played the part of a shrewd businesswoman, wearing business suits. She also played the part of Jarrett's girlfriend. In late 1998, Jarrett began a feud with Goldust that culminated in December at Rock Bottom: In Your House in a "Striptease match". During the match, Debra hit Goldust over the head with Jarrett's trademark guitar, enabling Jarrett to win. WWF Commissioner Shawn Michaels, however, disqualified Jarrett, and Debra had to strip due to the match's stipulations. As she stripped, The Blue Blazer and Jarrett covered her up. Debra, however, began utilizing a new strategy during matches, distracting Jarrett's opponents by unbuttoning her blouse.
The strategy helped Jarrett and partner Owen Hart defeat The Big Boss Man and Ken Shamrock to become World Tag Team Champions in January 1999. In February, Debra feuded with Ivory, making her in-ring debut in a mixed tag match on Monday Night Raw. The same month, Jarrett and Hart retained the tag titles in a tag match against Ivory's associates Mark Henry and D'Lo Brown at St. Valentine's Day Massacre with Debra's assistance. In March, the team lost their tag titles to the team of Kane and X-Pac. She also competed in her first single's match, against Ivory but lost via disqualification after Jacqueline and Terri Runnels attacked Ivory during the match. Hart passed away in May 1999 at Over the Edge. Later in the event, Debra and Jarrett lost a mixed tag team match against Nicole Bass and Val Venis. Debra and Jarrett were interviewed moments after Hart's fall from the rafters, where Debra was noticeably shaken and fighting back tears of concern for her friend, and was unable to stay in her persona.
On May 2, 1999, Debra was scheduled to take on Sable in a 'Nightgown' match, but was made to compete against Nicole Bass, against whom she lost. On May 10, 1999, Debra won the Women's Championship from Sable in an Evening Gown match. Usually, in an Evening Gown match, the woman who forcibly removes her opponent's dress wins. Because Sable removed Debra's dress, she therefore should have been the winner. Commissioner Shawn Michaels, however, ruled that he considered the woman who had lost her dress the winner, crowning Debra the new Women's Champion. Debra lost the Women's Title to Ivory on June 14, due to interference from Nicole Bass.
At SummerSlam in 1999 Jarrett faced D'Lo Brown. During the match, Debra and Brown's former tag team partner Mark Henry interfered on Jarrett's behalf, allowing him to win both the European Championship and the Intercontinental Championship. The following night, Jarrett awarded Henry the European title and gave Debra an assistant, Miss Kitty. Following an attack by Jarrett after losing a mixed tag match against Stephanie McMahon and Test, on September 26, Debra turned on Jarrett at Unforgiven and hit him over the head with a guitar in the middle of his match against Chyna for the Intercontinental Championship. Chyna pinned Jarrett, but referee Tom Prichard overturned the decision due to Debra's involvement. On the following episode of Raw, she participated in an inter-gender tag match with Chyna against the team of Jarrett and Prichard, in a winning effort.
Later that year, she participated in an eight-women sudden death match at Survivor Series, where she teamed with The Fabulous Moolah, Mae Young, and Tori in a winning effort against Ivory, Jacqueline, Luna Vachon and Terri Runnels. Debra subsequently stayed off television while her partner Stone Cold Steve Austin recovered from neck surgery. She reappeared in April 2000, acting as a guest ring announcer at Backlash. In the fall of that year, she played the role of Lieutenant Commissioner, the assistant of Commissioner Mick Foley.
Debra resigned as Lieutenant Commissioner on the March 5, 2001 episode of Raw to pursue managing again, while it was revealed on-screen that she was the wife of Stone Cold. Mr. McMahon gave her the duty of managing The Rock, who at the time was feuding with Stone Cold. In 2001, Debra would accompany Austin as he defected to the Alliance, with a running gag about her famous chocolate chip cookies being repulsive (although Debra herself remained oblivious to this). Following a miscommunication during a prank on Kurt Angle, Stacy Keibler and Shawn Stasiak accidentally dropped a bucket of milk on Debra. The following week, Debra beat up Keibler with a tray of cookies in a backstage segment, following a failed peace offering. In August, during an episode of SmackDown!, Debra also clocked Stone Cold in frustration with a cookie tray in the middle of the ring. The next week on Raw, she accompanied her husband to the ring for a match against Matt Hardy, and was involved in an altercation with Lita during the match.
In 2002, Debra was involved in a big backstage brawl with Stephanie McMahon after arguing over their respective husbands. Debra appeared sporadically thereafter, leaving the company in June 2002 with Austin.