Hardcore, who had debuted in the World Wrestling Federation in 1994, introduced his on-screen "cousin" Crash Holly on August 16, 1999. After arguing over who was the toughest Holly cousin, the pair brawled all over the arena for the rest of the show. They teamed up for the first time at SummerSlam, and spent the next few weeks alternating between being rivals and partners. From September on, the cousins started teaming together full-time, during which time they took to the gimmick of claiming themselves to be well over, so they could be considered "superheavyweights". On October 18, 1999, on Raw is War, Crash and Hardcore won the WWF World Tag Team Championship together, defeating the Rock 'n' Sock Connection, after Mankind refused to tag into the match, and Triple H interfered. They held the title for two weeks before dropping it back to Mankind and his new partner Al Snow on the November 4 episode of SmackDown!.
In early 2000, the Holly cousins began feuding over the Hardcore title. Hardcore had first won the title in early 1999, before Crash's debut; however, Crash won it on February 22, 2000, defeating Test. The pair soon started fighting each other for the title including in the "hardcore" Battle royal at WrestleMania 2000, where Crash started off as the champion, but Hardcore left as champion. Crash regained the title the day after WrestleMania, and soon after this, the Holly cousins had their last match as a team for over six months. During these months Crash concentrated on the hardcore division, winning the title 22 times, and earning the nickname "the Houdini of Hardcore". Hardcore legitimately broke his arm in a match against Kurt Angle and was sidelined for most of this time.
Reformation
In October 2000, Crash started feuding with Test and Albert. This set up the debut of another "cousin", Molly Holly. She debuted on November 6, 2000, on Raw, attacking Trish Stratus, who was managing T&A. This led to the Holly Cousins reuniting to feud with T & A and their manager, Trish Stratus. Although Hardcore and Crash had opportunities to win the Tag Team championship, they were never able to capitalize. They competed mainly in both the hardcore division and the tag title division for the next few months. Molly had multiple opportunities to win the Women's title, but was booked to lose them all. In early 2001, the Hollys began feuding with the Dudley Boyz. In May 2001, Crash and Hardcore, along with Bubba and D-Von Dudley became concerned about Molly's burgeoning relationship with Spike Dudley. This led to the Hollys-Dudleys feud intensifying, with both Spike and Molly caught in the middle. On May 28, 2001, the Dudley Boys famously put Molly through a table, with Spike lying on the table to try and protect her. As Molly and Spike's relationship progressed, the feud between the Hollys and the Dudleys worsened. This led to the final break-up of the Holly cousins, as Molly started accompanying Spike for his matches, Crash joined the Raw brand until 2003, and Hardcore was re-injured in September 2002.
Aftermath
Crash competed on Raw and later traded to SmackDown! until his release from WWE on June 30, 2003. He later died on November 6, 2003. Molly eventually dumped Spike, and went on to become a two-time Women's champion. On April 12, 2005, Molly left the company and retired from full-time wrestling. Hardcore was the final Holly to be released from the company, on January 16, 2009.