5. Randy Orton
> Most Hated Wrestler of the Year awards: 5
> WWE debut: 2002
> WWE appearances: 808
> Daily avg. Wikipedia page views: 3,829
The son of WWE Hall of Famer “Cowboy” Bob Orton and the grandson of “The Big O” Bob Orton Sr., Randy Orton is a third-generation wrestler who in 2004 became the youngest WWE World Heavyweight Champion at just 24 years old. While Orton debuted in the WWE as a face and has been voted the Most Popular Wrestler of the Year or was runner-up on several occasions, “The Viper” has expressed his preference for playing heel. Orton has made several memorable heel turns throughout his young career, executing his signature RKO move — a finishing jump cutter maneuver based on his initials Randy Keith Orton — on allies and enemies alike.
4. Greg Valentine
> Most Hated Wrestler of the Year awards: 4
> WWE debut: 2005
> WWE appearances: 2
> Daily avg. Wikipedia page views: 508
Greg Valentine’s 35-year tenure as a professional wrestler traverses several eras of sports entertainment, spanning intermittent stints in the NWA, WCW, and WWE. One of Valentine’s most notorious angles played out in 1977, when he broke former NWA U.S. Heavyweight Champion “Chief” Wahoo McDaniel’s leg in a figure-four leg lock during a match for the title and began wearing a T-shirt that read “I Broke Wahoo’s Leg.” Other moments that contributed to Valentine’s villain reputation include his destruction of the WWE Intercontinental Championship belt after losing it to Tito Santana in 1985.
3. Kurt Angle
> Most Hated Wrestler of the Year awards: 8
> WWE debut: 1995
> WWE appearances: 384
> Daily avg. Wikipedia page views: 3,824
While Kurt Angle embodied characteristics typically reminiscent of a face — a patriot donning red, white, and blue who stressed his three I’s — intensity, integrity, and intelligence — as well as other American ideals, the Olympic athlete drew heat at his 1999 televised WWE debut as fans met him with boos and signs criticizing his billing as a “real athlete.” Angle’s heel status is emblematic of the shift in audience tastes during the Attitude Era of the late 1990s, in which fans began to favor edgier, more anarchic personalities like Steve Austin and The Rock. While Angle spent most of his two-decade career as a villain, he was eventually embraced as a hero and was voted Most Popular Wrestler of the Year by PWI readers in 2003.
2. Ric Flair
> Most Hated Wrestler of the Year awards: 6
> WWE debut: 1993
> WWE appearances: 364
> Daily avg. Wikipedia page views: 5,411
Ric Flair is arguably one of the biggest figures in the history of sports entertainment. He perfected the “stylin’, profilin’, limousine riding, jet flying, kiss-stealing, wheelin’ n’ dealin'” persona that contrasted him with his more blue-collar rivals and helped elevate the National Wrestling Alliance in the 1980s. Along with Arn Anderson and a rotating cast of other wrestlers, Flair helped popularize the notion of a “cool heel” through the villainous Four Horsemen faction in the 1990s, embracing his arrogant gimmick in and outside of the ring. Flair has wrestled professionally for more than four decades and was voted the Most Hated Wrestler of the Year by PWI readers in 1978 and 1987 and runner-up in 1977 and 1986.
1. Triple H
> Most Hated Wrestler of the Year awards: 7
> WWE debut: 1995
> WWE appearances: 930
> Daily avg. Wikipedia page views: 6,313
Initially known to WWE fans as Hunter Hearst Helmsley, Triple H embraced a snobbish, aristocratic persona upon entering the WWE in 1995. He went on to co-found D-Generation X with Shawn Michaels and Chyna in 1997, helping usher in the Attitude Era that would define the WWE’s shift toward more violent and sexual content during the Monday Night Wars. While Triple H took on an executive role with WWE in 2011, he has remained an integral part of the squared circle, feuding with rising superstar Daniel Bryan as a member of the executive-led stable The Authority. In 2014, Triple H and his wife — fellow member of The Authority Stephanie McMahon — were jointly named the Most Hated Wrestler of the Year.