Keibler was born on October 14, 1979, in Rosedale, Maryland, the daughter of Patricia and Gary Keibler. Beginning at the age of three, Keibler took ballet, jazz, and tap dancing classes at Jean Kettell Studio of Dance in Dundalk, Maryland. She went to St. Clement Mary Hofbauer School in Rosedale for her early schooling. In 1990, Stacy won the title of Miss Maryland Pre-Teen, after competing for the title in Timonium, MD, and went on to win the National Miss Pre-Teen Crown.

Keibler began watching wrestling with her boyfriend at the time, Kris Cumberland. She can be seen in the crowd on an episode of Nitro in 1997 and the Starrcade pay-per-view before the television title match, dancing in an NWO Wolfpac t-shirt. In late 1999, Keibler entered a nationwide contest held by World Championship Wrestling to find a new member of the Nitro Girls dance troupe. In November, she defeated 300 other girls for a spot on the dance troupe and $10,000. Her winning routine was watched by 4.4 million viewers. Keibler performed dance routines every week on WCW's flagship show Monday Nitro under the name Skye. By 2000, Keibler was appearing on WCW as a Nitro Girl, attending school full-time, and cheering for the Baltimore Ravens. She soon accepted a larger role and became a valet using the stage name Miss Hancock (some weeks spelled "Handcock"), briefly serving as an associate for the tag team of Lenny Lane and Lodi dubbed Standards and Practices. Despite wearing business suits, her character was known to climb on top of the announcers' table and dance sensually. It was also during this period that she began using what would become her trademark ring entrance: slowly putting her forty-two inch legs through the second tier of ropes, pausing to let the crowd momentarily see her panties. At 5 feet 11 inches, Keibler was one of few women in professional wrestling tall enough to step over the middle of the three ropes that surround the ring. For a brief period, she dated David Flair (both on-screen and off), who was already involved in an on-screen relationship with Daffney. This led to Keibler's in-ring debut at the Bash at the Beach in a Wedding Gown match, which she lost after she removed her own gown. Hancock next briefly feuded with Kimberly Page, but the storyline ended abruptly when Page quit the company. Keibler and Flair then began a feud with the Misfits in Action stable, including a mud wrestling singles match against Major Gunns at New Blood Rising. During the match, she was kicked in the stomach, and she revealed herself to be pregnant the next night, beginning a new angle for herself and Flair. Two proposed endings to the storyline were for either Ric Flair or Vince Russo to be the father of her child. The angle, however, ended prematurely, as she revealed the pregnancy to be false, broke up with David Flair, and was taken off of television. When she returned, she was known by her real name on-screen. On the March 12, 2001 edition of Nitro, Keibler revealed Shawn Stasiak as her "baby." She helped Stasiak defeat Bam Bam Bigelow in the final edition of Nitro two weeks later on March 26.

what dance troupe?
Nitro Girls