The McMahon-Helmsley Faction was a large heel stable which lasted from late 1999 eventually faded away by early 2001. The group began with Triple H's victory over WWF chairman Vince McMahon at Armageddon in December 1999. The reason for this match was due to HHH and D-Generation X's feuding with McMahon and his associates (the remnants of the Corporation). On a edition of RAW IS WAR, Vince's daughter Stephanie McMahon was to "marry" her (then) real life lover Test; however, HHH came out and played a video showing a drugged Stephanie "marrying" him (HHH) at a drive-thru chapel. At Armageddon HHH battled Vince, if HHH won then he got a title shot on RAW. In a shocking twist of events, Stephanie turned on her father during the match and helped secure a victory for her new husband. The night after Armageddon, HHH annouced the start of the McMahon-Helmsley Era, HHH's capture of the Heavyweight Championship, along with Road Dogg and Billy Gunn's dominance of the tag team division helped cement the faction's power.

The groups was immediately opposed by Mick Foley (then wrestling as Mankind) who appeared on RAW to tell both HHH and Stephanie that he thought that the McMahon-Helmsley Era "Kinda s*cks." This lead to Mankind's firing, but he was brough back on an edition of SmackDown! thanks to The Rock and other WWF wrestlers who threatened to walk out of the WWF if Mankind was not re-instated.

At Royal Rumble 2000 Mankind (now wrestling as Cactus Jack) was defeated by HHH in a classic Street Fight ; The Rock went on to win the rumble.

At WrestleMania 2000 Vince McMahon turned on the the Rock and secured a victory for HHH, however the next month at Backlash the Rock with help from Stone Cold Steve Austin lifted the title from HHH ending his 3 month title reign.

Over the course of the next few months, the McMahon-Helmsley Faction was opposed from a variey of wrestlers, including The Undertaker, Kane, the Dudley Boyz, Chris Jericho, Too Cool and Rikishi. Mick Foley became Commissioner of the WWF in mid 2000 and aided in the fight against the Faction. Steve Austin's return in October 2000 further aided in the dismantling of the group. By late 2000, with Road Dogg out of the WWF, Billy Gunn as a singles competitor and X-Pac out on injury, the group was largely forgotten. However the following year saw Austin turn heel and join HHH and Vince McMahon. Though some would not call this part of the McMahon-Helmsley Era, it did ensurer HHH's staying at the top of the WWF.

The group came to an end with HHH being sidelined on injury, and the focus of storylines on the combined WCW-ECW invasion.

In early 2002, HHH and Stephanie ended their on-screen relationship, which finally brought the McMahon-Helmsley Era to an end. By this time, the two had begun a real-life relationship, which culminated in their marriage in October 2003.

The group is best remembered for unprecedented victories at huge events like WrestleMania where HHH shunned tradition and became the first heel to ever win a WrestleMania main event. The group is also remembered for engaging in rivalries with many different WWF superstars, and for being able to gain huge amounts of heat from crowds.

At its height, the McMahon-Helmsley Faction included the following superstars:

• Triple H
• Stephanie McMahon-Helmsley
• Road Dogg
• Billy Gunn
• X-Pac
• Vince McMahon
• Shane McMahon
• Gerald Brisco
• Pat Patterson
• Torie

• Billy Gunn left the group before the joining of McMahon and his associate.