Crash Holly debuted as the storyline cousin of Bob "Hardcore" Holly, on the August 16, 1999 episode of Raw is War. They became known as The Holly Cousins. Their relationship was a strained one, and Hardcore frequently threatened Crash. When they took the gimmick of claiming to be "super heavyweights", over 400 lb each, Crash would carry a scale to ringside to "weigh in" before matches.
Crash made his pay-per-view debut at SummerSlam in August, where The Holly Cousins wrestled in a Tag Team Turmoil match, won by the Acolytes Protection Agency.
On October 17, at No Mercy, The Holly Cousins defeated The New Age Outlaws by disqualification. The next night on Raw is War, they defeated The Rock 'n' Sock Connection for the WWF Tag Team Championship. They held the title until the November 4 SmackDown!, when they lost it to Mankind and his new partner, Al Snow.
In early 2000, Crash Holly joined the hardcore division. On the February 24 episode of SmackDown!, he defeated Test to begin his first of 22 Hardcore Championship reigns. He decreed that he must defend the championship twenty four hours a day, seven days a week. This was known as the "24/7 Rule". This meant that the title was permanently contested, not just in sanctioned matches, and could change hands anywhere, anytime anyone pinned the champion, so long as a WWF referee counted the fall. Holly was frequently attacked by other wrestlers in unlikely locations, including an airport, a funhouse, a circus, and his hotel room. Though he was often pinned, he usually immediately regained the title. His most common tactic was to sneak a pin, often after the champion had been beaten down by someone else, and quickly run backstage, away from possible challengers. This turned him into a crowd favorite and earned him the nickname "Houdini of Hardcore". He frequently defended the championship against non-wrestlers, including referees and road agents, like Gerald Brisco and Pat Patterson. He had a long feud with The Mean Street Posse (Pete Gas, Rodney and Joey Abs) over the title.
At Rebellion, Crash defeated William Regal to win the WWF European Championship. He dropped it back to Regal two days later.
In late 2000, another of Crash's storyline cousins, Molly Holly, was introduced. In 2001, The Holly Cousins feuded with The Dudley Boyz. In the course of this feud, Molly began a romantic relationship with Spike Dudley, leading to internal disputes within each family, as well as a Romeo and Juliet-style angle between the six of them.
On the March 18, 2001 epiode of Heat, Crash defeated Dean Malenko to win the Light Heavyweight Championship. He held it for over a month before dropping it to the debuting Jerry Lynn, on the April 29 Heat.
In May 2001, Holly and Hardcore briefly reunited as a lower card team.
When the WWF was renamed World Wrestling Entertainment and divided into two Raw and SmackdDown brands, Holly was assigned to the Raw roster, where he had little success. He jumped ship to SmackDown! on the September 2, 2002 episode of Raw during a match with Jeff Hardy. Earlier, Raw General Manager Eric Bischoff was informed that a Raw wrestler would leave to reunite with a relative on SmackDown!, and ordered a beatdown on Hardy, who he wrongly suspected of planning to join his brother, Matt Hardy.
In his first SmackDown! match, on September 5, he defeated The Hurricane. He then feuded with Cruiserweight Champion Jamie Noble. On the October 3 SmackDown!, Noble defeated Holly to retain the title.
On the December 19 SmackDown!, Holly teamed with Bill DeMott to defeat Noble and Nunzio. After the match, DeMott turned on Holly and attacked him. This led to a match on the next SmackDown!, which DeMott won.
After being sidelined for four months, Holly returned on the April 24, 2003 episode of SmackDown!. He soon joined Matt Hardy and Shannon Moore in the Mattitude Followers stable. As Crash was Moore's alleged apprentice, Hardy also referred to him as a "Moore-on".
Holly was released from WWE on June 30, 2003.
Crash Holly died on November 6, 2003.