'Stone Cold' Steve Austin

Austin trained for 5 months at Chris Adam's wrestling school and defeated Frogman Lablanc in his ring debut as Steve Williams receiving $40 for the night. Steve turned heel on his mentor, Chris Adams and defeated him on several occasions. Austin won the TWF (Texas Wrestling Federation) tag titles with The California Stud (Rod Price) on November 10th 1990, by defeating The Angel of Death & Abdullah the Butcher. On January 25th 1991, Austin captured the USWA Southern title from Jeff Jarrett.

In April 1991, 'Stunning' Steve Austin arrived in WCW, he had a valet, Vivacious Veronica, but she was soon replaced by Lady Blossom (his then real life wife Jeannie). Austin beat Bobby Eaton for the WCW Television Title on June 3rd 1991. Steve joined Paul E. Dangerously's (Paul Heyman) Dangerous Alliance, which included 'Ravishing' Rick Rude, 'Beautiful' Bobby Eaton, 'The Enforcer's' Arn Anderson & Larry Zbyzsko, and Madusa. Barry Windham defeated Austin for the TV title on April 27th 1992, but he regained the tile for a 2nd time four weeks later, eventually losing it to Ricky 'The Dragon' Steamboat on September 2nd. When Dangerously left WCW, Austin formed a tag team with Brian Pillman dubbed The Hollywood Blondes and captured the WCW Tag Team Championship from Ricky Steamboat & Shane Douglas on March 2nd 1993. They eventually lost the titles to Arn Anderson & Paul Roma on August 18th when Steven Regal had to substitute for the injured Pillman. Austin returned to singles competition with a new manager, Colonel Parker. On December 27th at Starrcade, Austin defeated Dustin Rhodes in a best 2 out of 3 falls match for his the United States Championship. He eventually lost the title to Ricky Steamboat on August 24th 1994. Austin was awarded his 2nd U.S. title on September 18th when Steamboat was unable to defend it due to injury, but he lost it the same night to Jim Duggan. In September 1995 Eric Bischoff terminated Austin's $300,000 dollar per year contract due to a serious muscle tear injury which occurred during a tour of Japan and perceived lack of 'marketability'.

Austin debuted in ECW as 'The Extreme Superstar' Steve Austin, on September 23rd 1995, due to injury Austin mostly used the microphone in his brief ECW stint. By the end of 1995 Austin signed with the WWF. He entered the WWF as The RingMaster, managed by 'The Million Dollar Man' Ted DiBiase and was awarded the Million Dollar belt on December 18th. He made his WWF Pay-Per-View debut at the Royal Rumble on January 21st 1996, where he eliminated Bob Holly, but was eliminated by Fatu (Rikishi). Austin then began a feud with Savio Vega. Whilst at home his then wife told him to drink his tea before it was stone cold, a new gimmick was born! At WrestleMania XII 'Stone Cold' Steve Austin defeated Vega. At In Your House 8 on May 28th, Stone Cold lost a strap match to Vega which meant DiBiase had to leave the WWF. Stone Cold won the 1996 King of the Ring, defeating Marc Mero and Jake 'The Snake' Roberts. During the coronation ceremony Stone Cold said his famous quote, "Austin 3:16 says I just whipped your Ass!" for the 1st time due to Jake's religious beliefs. Stone Cold began a verbal assault on Bret 'The Hitman' Hart leading to a match at Survivor Series on November 17th. Stone Cold was defeated by Hart in a classic encounter. Stone Cold won the 1997 Royal Rumble after he was eliminated, but re-entered the Battle Royal to eliminate Bret Hart because none of the officials saw it. Stone Cold faced Bret Hart in a submission match at Wrestlemania XIII, guest referee Ken Shamrock stopped the match after Austin, covered in blood, passed out in the sharpshooter. On the May 25th edition of RAW, Stone Cold teamed up with Shawn Michaels to defeat Owen Hart & the British Bulldog for the WWF World Tag Team Championship. Austin & Michaels were unable to co-exist as a team and on June 11th at King of the Ring the then current tag team champions faced each other for the 1st time. The match resulted in a no-contest when both men were disqualified for attacking the referees. When Michaels got injured the tag titles were declared vacant and Stone Cold needed a partner for a rematch with Owen Hart & the Bulldog on July 14th. Mick Foley, who had been unsuccessfully petitioning Stone Cold to pick him for weeks using his Mankind persona, tried a different tact as he arrived as Dude Love. Stone Cold & Dude Love successfully captured the WWF Tag Team Championship. Stone Cold won his 1st WWF singles title, the Intercontinental Championship, at Summerslam on August 3rd at the expense of Owen Hart, but in the process suffered a serious neck injury when Hart pile drove Austin. As a result Austin was forced to forfeit both the Intercontinental and Tag Team Championship on September 7th. Stone Cold's feud with WWF owner Vince McMahon began on September 22nd when the 'Texas Rattlesnake' gave McMahon a Stunner during a RAW broadcast from Madison Square Garden. On November 11th Austin regained the Intercontinental title once again at the expense of Owen Hart at the infamous Survivor Series in Montreal where McMahon 'screwed' Bret Hart out of the WWF title. Having already defended the IC title against Rocky Maivia (The Rock) the night before at the DX PPV, Austin refused to do it again when ordered to by McMahon. Instead on the December 8th edition of RAW, he forfeited the title by throwing it off a bridge into a river stating that he had bigger fish to fry.

Stone Cold won the Royal Rumble for the 2nd year in a row to earn a shot at the WWF Championship at Wrestlemania XIV. Stone Cold defeated Shawn Michaels to win his 1st WWF Championship on March 29th 1998. The teased Austin-McMahon match on the April 13th edition of RAW ended NITRO's 83-week consecutive winning streak in the Nielsen ratings war. On June 28th, Kane defeated Stone Cold for the WWF title at the King of the Ring in a First Blood match. However the next night on RAW Stone Cold won his 2nd WWF Championship by defeating Kane. Stone Cold briefly held the Tag Team Championship for a 3rd time along with The Undertaker having defeated Kane & Mankind on July 26th. However they lost the titles back to Kane & Mankind on August 10th. McMahon ordered Austin to defend the WWF Championship against both Kane & The Undertaker at Breakdown on September 27th, both The Undertaker and Kane pinned Austin, but no winner was announced. A tournament was held to declare a new champion at the Survivor Series on November 15th, which was won by The Rock who also joined McMahon's Corporation. Stone Cold won the right to compete in the 1999 Royal Rumble by defeating The Undertaker in a Buried Alive match at the Rock Bottom Pay-Per-View on December 13th 1998. Stone Cold surprisingly lost the Rumble to Vince McMahon thanks to help from The Rock but he earned the right to a title shot by beating McMahon in a Cage match at the St. Valentine's Day Massacre on February 14th. Stone Cold defeated The Rock at Wrestlemania XV for his 3rd WWF Championship. Stone Cold lost the title to The Undertaker at Over the Edge on May 23rd but regained it on June 28th for the 4th time. Stone Cold lost the title to Mankind in a Triple Threat match also featuring Triple H at Summerslam on August 22nd, after the match Triple H brutally assaulted Austin setting up a feud. At Survivor Series on November 14th, Stone Cold was 'run-over' by a car.

In January 2000, Austin had surgery to remove bone spurs from his neck. Stone Cold helped The Rock beat Triple H for the title at Backlash on April 30th. On September 13th 2000, Austin married Debra in Las Vegas, NV. Stone Cold returned to the WWF in time for Unforgiven in search of the person who ran him over. On the October 9th episode of RAW, Rikishi revealed himself as the hit and run driver. Stone Cold faced Rikishi in a No Holds Barred match at No Mercy on October 22nd and was arrested during the match when he tried to run over Rikishi. Triple H revealed himself as the man behind the plan to run down Stone Cold and at Survivor Series on November 19th, the two fought in a no DQ match. The match resulted in a no-contest after Stone Cold used a fork lift truck to hoist Triple H up in a car and then drop it onto the ground in the parking lot. Stone Cold won the Royal Rumble for a record 3rd time on January 21st 2001. At No Way Out on February 25th, Stone Cold faced Triple H in a Three Stages of Hell, best 2 out of 3 falls match. Stone Cold won the 1st fall in a straight wrestling match. Triple H won the 2nd in a Street Fight, and the 3rd in a Cage, when both he & Stone Cold knocked one another out with a sledgehammer and a barbed wire board and �The Game� fell on top of �The Rattlesnake� to gain the victory. At Wrestlemania XVII on April 1st in Houston, Texas, Stone Cold defeated The Rock for his 5th WWF Championship when he accepted Vince McMahon's help to beat The Rock senseless with a steel chair turning heel in the process. Stone Cold joined forces with Triple H to defeat The Undertaker & Kane for his 4th WWF Tag Team Championship at Backlash on April 29th. Stone Cold & Triple H lost the tag titles to Chris Benoit & Chris Jericho on May 21st. Austin defended the WWF Championship in a Triple Threat match with Benoit & Jericho at King of the Ring on June 24th. During the match the 'Bionic Redneck' was attacked by the wCw Champion, Booker T. At Invasion on July 22nd, Stone Cold turned against the WWF, and joined the wCw/ECW alliance. At Unforgiven on September 23rd, Stone Cold lost the WWF Championship to Kurt Angle but regained it for his sixth title reign on October 8th. At Vengeance on December 9th, Stone Cold lost the title to Chris Jericho having defended it once already that evening against Angle. At Wrestlemania X8 on March 17th 2002, Stone Cold defeated Scott Hall of the nWo. Afterwards Austin mysteriously did not appear on WWF programming for several weeks. At Backlash on April 21st, Stone Cold lost a No. 1 contender�s match to The Undertaker. At Judgement Day on May 19th, Stone Cold defeated The Big Show and Ric Flair in a handicap match. Following Austin's failure to appear at the June 10th edition of RAW, the WWE posted the following statement on June 13th 2002, "Stone Cold Steve Austin is no longer an active member of WWE�s talent roster."

Austin returned at No Way Out on February 23rd 2003 to defeat Eric Bischoff, the man who had terminated his WCW contract in 1995. At Wrestlemania XIX on March 30th, Stone Cold was defeated by The Rock. On the April 28th edition of RAW, Stone Cold was announced as the Co-General Manager with Bischoff. At Survivor Series on November 16th, Stone Cold�s Team, consisting of Booker T, RVD, HBK, & The Dudley Boyz, were defeated by Bischoff�s Team, consisting of Y2J, Scott Steiner, Christian, Mark Henry, & Randy Orton. As a result of this Austin lost his job as Co-GM. On December 29th Stone Cold returned to RAW as the Sheriff. On April 16th 2004, WWE.com stated: -

"After months of negotiations, the WWE and Steve Austin have been unable to come to terms on a new contract and as a result have mutually agreed to part company. Both parties have left the door open to work together again in the future and the WWE wishes Steve the very best in his future endeavors."

In early 2005, WWE announced that Austin had agreed to a movie contract with WWE Films. Austin appearred at Wrestlemania 21 on April 3rd 2005, during a segment of Piper's Pit.

Ric Flair

In 1967, Flair was a high school state Heavyweight Champion in Wisconsin. Flair battled George 'Scrap Iron' Gadaski to a 10-minute draw in his 1972 pro debut for the AWA. 'The Nature Boy' moved on to the NWA, where he beat Paul Jones to win his first title, the NWA Mid-Atlantic Television Title, which later became the NWA World Television Title on June 3rd 1975, however he lost the title back to Jones seven days later. On October 4th 1975, Flair was involved in a plane crash in Wilmington NC, which resulted in his neck being broken in three different places. The doctors told him he would never wrestle again. But by December 26th 1976, Flair, along with partner Greg 'The Hammer' Valentine, captured the NWA World Tag Team Championship by defeating Gene & Ole Anderson. They lost the belts back to Gene & Ole on May 8th 1977. Flair regained the NWA TV Title for a second time by defeating Rufus Jones that same month. He held the title for less than two months as Ricky 'The Dragon' Steamboat defeated him for the belt on June 22nd 1977. On July 29th, Flair beat Bobo Brazil for his first NWA United States Title. On October 30th, Flair along with Valentine regained the tag titles from Gene & Ole Anderson. Flair lost the US Title to Steamboat on November 11th. Flair & Valentine were stripped of the tag titles in April of 1978 when Flair regained the US Title from Mr. Wrestling (Tim Woods) that same month. Steamboat once again beat Flair for the US Title on December 18th 1978, but 'The Nature Boy' regained the title from 'The Dragon' on April 1st 1979. Flair vacated the title when he won the NWA Tag Team Championship for a third time, with new partner Blackjack Mulligan, from Baron Von Raschke & Paul Jones on August 8th 1979. Flair & Mulligan lost the title back to Von Raschke & Jones fourteen days later. Flair re-captured the US Title by defeating 'Superfly' Jimmy Snuka on April 19th 1980. He lost the belt to his former tag team partner Greg Valentine on July 26th, but regained the title for a fifth time on November 24th. Flair lost the title to 'Rowdy' Roddy Piper on January 27th 1981.

On September 17th 1981, Flair won his first World title by defeating 'The American Dream' Dusty Rhodes in Kansas City, MO, for the NWA World Heavyweight Title. Flair lost the title to Harley Race on June 10th 1983. Flair has said that the greatest moment in his wrestling career came at the very first Starrcade on November 24th 1983, when he defeated the then 7-Time World Champion Harley Race in a Steel Cage match in Greensboro, NC, to regain the NWA Title. Although Flair is said to have lost the title back to Race on March 21st 1984, in New Zealand, and then regain it two days later in Singapore, this is not officially acknowledged. The late 'Texas Tornado' Kerry Von Erich defeated Flair for the title in Irving, Texas, on May 6th 1984, only for Flair to regain the title, officially for the third time, a few weeks later on May 24th whilst touring Japan. Flair formed the original Four Horsemen in June of 1986 with Tully Blanchard, Ole, and Arn Anderson, they were managed by James J. Dillon. Although in later year�s names such as, Lex Luger, Barry Windham, Sting, Brian Pillman, and Chris Benoit would be included among the ranks of the Horsemen, Ric Flair was constant throughout. Dusty Rhodes defeated Flair for his title on July 26th 1986, but Flair regained it for a fourth time on August 9th. On September 25th 1987, 'Rugged' Ronnie Garvin defeated Flair for the belt, but he regained it for his fifth official title reign at Starrcade on November 26th. In the match that 'made' Sting, both he and Flair wrestled to a forty-five minute draw at the first Clash of the Champions on March 27th 1988. Steamboat relieved 'The Nature Boy' of the NWA Title at the Chi-Town Rumble PPV on February 20th 1989, but Flair regained it a few months later on May 7th. At Starrcade on December 13th 1989, Flair competed in an Iron man tournament to determine who would dominate the 90's. Flair beat The Great Muta, drew against Lex Luger, and then lost to Sting in the final. On July 7th 1990, Flair lost the NWA Title to Sting at The Great American Bash. Flair regained it for seventh time on January 11th 1991. On March 21st 1991, at the Tokyo Dome in Japan, Flair lost the NWA Title to Tatsumi Fujinami in a controversial match. However because WCW had started to refer to the belt as the WCW Title around this time, the company continued to recognise Flair as the Champion. At the first Superbrawl on May 19th 1991, 'The Nature Boy' defeated Fujinami, supposedly to regain the NWA Title, but this title change was not acknowledged by WCW as they already considered Flair to be the WCW Champion and did not consider the titles to be separate. Therefore, at this point in Flair�s career he was considered to be a 7-Time NWA World Heavyweight Champion, even though the title had begun to be referred to as the WCW Title, and Flair had arguably lost and regained the title on two other occasions.

Flair joined the WWF after being fired by then WCW boss Jim Herd on July 2nd 1991. Some say this was because Flair refused to do the 'job' for Lex Luger at The Great American Bash. However Flair has stated that it was Barry Windham, and not Luger, whom he was asked to drop the title to several days before, and the reason he did not was because back then all champions had to pay a deposit to hold the title belt and the company were refusing to pay him back his money. Therefore Flair claimed the belt was his and the NWA Title was declared vacant for the first time in its history. Flair took the belt with him and paraded it around the WWF claiming to be the 'real worlds champion' seeing as how he actually owned it, meanwhile WCW had a new belt made and Luger won the WCW Title at the The Great American Bash by defeating Barry Windham. Whilst in the WWF, Flair�s entourage included Bobby 'The Brain' Heenan in a 'financial advisor' role, and Mr. Perfect (Curt Hennig), who accompanied �The Nature Boy� to the ring as his 'executive consultant'. In reality Hennig was unable to wrestle during this period due to a back injury suffered at the hands of Bret Hart during their match at Summerslam in 1991. At the Royal Rumble on January 19th 1992, Flair outlasted 29 other men to win the vacant WWF Championship. Although this was Flair�s first WWF Championship, it is considered to be his eight World title overall. At Wrestlemania VIII on April 5th 1992, Flair lost the title to 'Macho Man' Randy Savage as part of a double-main event. Vince McMahon had originally wanted Flair versus Hulk Hogan as the main-event, but as insurance for the eventuality that Flair might rejoin WCW, McMahon had signed 'Psycho' Sid Vicious (known as Justice in this brief WWF stint) with the promise that he would wrestle Hogan at the next Wrestlemania. Therefore the compromise of a double-main event with Flair against Savage and Hogan against Sid was reached. Flair regained the WWF Championship from the 'Macho Man' for his second WWF title reign on September 1st 1992, he held the title for little over one month before dropping it to Bret 'The Hitman' Hart on October 12th. At the Survivor Series, Flair & Razor Ramon (Scott Hall) were scheduled to face the 'Mega-Maniacs' team of Savage & The Ultimate Warrior. However the Warrior had left due to 'differences' between himself and Vince McMahon over the direction of his character with regards to the title situation. Therefore Flair's former 'executive consultant' Mr. Perfect, was announced as Savage's partner. Perfect & Savage prevailed via DQ. Following another impressive performance at the 1993 Royal Rumble, Flair lost a retirement match to Perfect the next night on RAW as he had agreed to return to WCW.

Flair returned to WCW at Superbrawl III on February 21st 1993. Flair formed a new version of the Four Horsemen, this time with 'Pretty' Paul Roma, Ole and Arn Anderson. At Beach Blast on July 18th 1993, Flair defeated former member of the horseman, Barry Windham, for his eighth NWA World Heavyweight Title, and his tenth overall. However, when WCW later withdrew from the NWA, recognition was dropped and Flair was recognised as the "WCW International" World Heavyweight Champion. Flair lost that title to 'Ravishing' Rick Rude on September 19th at Fall Brawl. At Starrcade on December 27th, Flair defeated Vader to win the WCW World Heavyweight Title, making him an eleven time World Champion. After Spring Stampede on April 17th 1994, the title was held up after a championship match with Ricky Steamboat ended in a double pin. Although Flair won the rematch on April 24th, this is the third title victory that is not officially recognised as Flair did not actually lose the championship. Therefore although it could be argued that at this time Flair was a fourteen time World Champion, officially he is only recognised as an eleven time World Champion at this point in his career. On June 23rd, Flair beat Sting to unify the "WCW International" World Heavyweight Title with the WCW World Heavyweight Title. After Hulk Hogan joined WCW, it was announced that the dream match up of Hogan versus Flair would finally take place on July 17th at Bash at the Beach. Flair lost the match and the title to Hogan. At Halloween Havoc on October 23rd, Flair lost a 'Steel Cage Retirement' match to Hogan. However Flair soon returned after Hogan & Savage lobbied for him to be re-instated. At Fall Brawl on September 17th 1995, Flair wrestled and lost to long time friend and fellow Horseman, Arn Anderson. At Starrcade on December 27th 1995, Flair beat Savage for the WCW World Heavyweight Title, making him a twelve time world champion. Flair lost the title back to Savage on January 22nd 1996, but regained it in a Steel Cage match at Superbrawl VI on February 11th, and was recognised as a thirteen time world champion by WCW. Although it could be argued that this was actually Flair's sixteenth world title because WCW did not recognise Flair's loss or recapture of the NWA title with Race in 1984, Fujinami in 1991, or when the WCW title was held up between matches with Steamboat in 1994. On April 22nd, Flair lost the title to The Giant (Paul Wight). At The Great American Bash on June 16th 1996, 'The Nature Boy' teamed up with fellow horseman Arn Anderson to take on the NFL duo of Kevin Greene (then of the Carolina Panthers) and Steve 'Mongo' McMichael (formerly of the Chicago Bears). Flair & Anderson prevailed when they paid 'Mongo' to turn on his partner, thus joining the Horsemen. On July 7th 1996, at Bash at the Beach, Flair won the US Title for a sixth time when he defeated Konnan, but had to vacate the title in November due to injury. At Slamboree on May 18th 1997, Flair returned, and along with Roddy Piper & Kevin Greene, defeated the NWO trio of Scott Hall, Kevin Nash, & Syxx (Sean Waltman), in his hometown of Charlotte, North Carolina. Later that year, Ric�s best friend, Arn Anderson was forced to retire due to injury. Curt Hennig was offered his �spot� in the Horsemen, but instead betrayed and viciously attacked Flair at Fall Brawl on September 14th. A feud ensued between Flair and Henning for much of the rest of the year. At Souled Out on January 24th 1998, Flair was defeated once again by Bret Hart. Flair did not work for WCW throughout much of 1998 due to a dispute with the company over his missing a television taping in favour of watching his son win a wrestling tournament, even though he claimed to have given proper notification. On the September 14th 1998 edition of NITRO, Flair reformed the Horsemen with Arn Anderson, Dean Malenko, Chris Benoit and Steve McMichael. On March 14th 1999, at Uncensored, Flair won the WCW World Heavyweight Title once again by defeating 'Hollywood' Hulk Hogan in a 'First Blood� Steel Cage match. WCW would recognise this as his fourteenth World title. Flair lost the title the following month to Diamond Dallas Page during a Four Corners match that included Sting, Hogan, & Savage as the special referee. On the May 15th 2000 edition of NITRO, Flair defeated 'The Chosen One' Jeff Jarrett for the WCW World Heavyweight Title, making him a fifteen time officially recognised World champion, but was stripped of the belt shortly afterwards by Vince Russo. On May 23rd, Kevin Nash defeated Jarrett & Scott Steiner in a Triple Threat match for the title. Because Ric had never really lost the belt, Nash handed the WCW World Heavyweight Title back to Flair on May 29th, making �The Nature Boy� a sixteen time World Champion in the process. Unfortunately Flair would lose the title back to Jarrett later that same night. In the summer of 2000 Flair underwent rotator cuff surgery. At the last ever WCW PPV, Greed on March 18th 2001, the duo of Jeff Jarrett and �The Nature Boy� were beaten by Flair�s old nemesis, Dusty Rhodes, along with his son Dustin (a.k.a. Goldust). On the last ever NITRO on March 26th, Ric Flair and Sting locked up for one last time as the man in black defeated 'The Nature Boy'.

On November 19th 2001, Flair returned to the WWF when he appeared on RAW as the 'half owner' of the company having purchased Shane & Stephanie McMahon's stocks. At the Royal Rumble on January 20th 2002, Flair defeated Vince McMahon in a Street-Fight. At Wrestlemania X-8 on March 17th, Flair was defeated by The Undertaker in a No-DQ match. The next night it was announced that a 'brand extension' would take place with Flair controlling RAW and McMahon controlling SmackDown! Both would also have their own roster of talent. Flair and the RAW 'brand' acquired the services of such names as Steve Austin, The Undertaker, and the combined unit of the NWO, Kevin Nash, Scott Hall, & X-Pac (Sean Waltman). Whilst McMahon drafted such talent as The Rock, Kurt Angle, Chris Benoit, and 'Hollywood' Hulk Hogan, for SmackDown! Although Flair would eventually lose his co-ownership to McMahon in a match, it was not long before he had aligned himself with Triple H in a new stable named Evolution also featuring newcomers Randy Orton and Batista. At Armageddon on December 14th 2003, Flair along with Batista, captured the World Tag Team Championship by winning a Tag Team Turmoil match, eventually defeating The Dudley Boyz. Although Flair & Batista lost the belts to Booker T & RVD on February 16th 2004, they regained them on March 22nd, before losing them to Chris Benoit & Edge on April 19th. At Unforgiven on September 18th 2005, Flair defeated Carlito for the Intercontinental Championship.

Triple H

LeVesque made his wrestling debut in March 1992 for the International Wrestling Federation (of Massachusetts). LeVesque used the ring name Terra Ryzing, and the inverted Indian Deathlock as his finisher. In July 1992, Ryzing captured the IWF title from Mad Dog Richard. Ryzing's independent victories earned him a WCW tryout on February 4, 1994. Ryzing defeated little known Keith Cole in Atlanta, GA.

LeVesque entered WCW as Jean Paul LeVesque. He was primarily used as jobber. LeVesque received a shot at Larry Zbyszko's WCW World Television Title on June 2nd, 1994, in Gainesville, GA. The match resulted in a double count-out.

In May 1995, LeVesque left WCW and signed with the WWF. He changed his gimmick again to a Greenwich, Connecticut Blue-blood snob called Hunter Hearst Helmsley. Helmsley started using a new finisher, a double-underhook piledriver called the Pedigree. In his WWF PPV debut, Helmsley defeated Bob Holly at Summerslam '95 in Pittsburgh, PA. On March 31st 1996 Helmsley was destroyed in less than two minutes by The Ultimate Warrior at Wrestlemania XII. He blamed his ring valet Sable (Rena Mero) for the defeat. On May 19th, 1996, Hunter defeated Razor Ramon (Scott Hall) in his final WWF match. Breaking kayfabe, the clique, Diesel (Kevin Nash), Helmsley, Shawn Michaels, and Razor (Hall) took bows in front of the Madison Square Garden crowd after the Michaels/Diesel steel cage match. Helmsley was supposed to win the 1996 King of the Ring, but was punished for the MSG act by going on 'job patrol'. Helmsley sought the guidance of Mr. Perfect (Curt Hennig). Helmsley captured the WWF Intercontinental title on the October 21st, 1996 edition of RAW by defeating Marc Mero (Husband of Rena Mero), when Hennig turned on Mero, clobbering him with a chair. At the 1997 Royal Rumble, Helmsley defeated Goldust (Dustin Rhodes). He lost the title to The Rock (when he was known as Rocky Maivia) on February 13th 1997. Helmsley introduced a new muscular female bodyguard at Wrestlemania XIII by the name of Chyna (then real-life girlfriend Joanie Laurer). Helmsley became the 1997 King of the Ring by defeating Ahmed Johnson in the semi-finals and Mankind (Mick Foley) in the finals.

In August 1997, Helmsley and Chyna aligned themselves with Shawn Michaels to form 'Degeneration X'. Around this time Hunter started to be referred to as Triple H and along with HBK ('The Heart Break Kid' Shawn Michaels), Chyna, and for a short time, the late Rick Rude, set about antagonising members of the Hart Foundation (Bret & Owen Hart, The British Bulldog, & Jim 'The Anvil' Neidhart. On September 20th, 1997, DX assisted Michaels in beating The British Bulldog for the European title on his home soil at the English PPV One Night Only. On December 11th Michaels allowed Helmsley to pin him and claim the WWF European title. Goldust disguised himself as Helmsley, and on January 20th, 1998, 'Hunter-dust' lost to the late Owen Hart, who was declared the new European Champion by then WWF Commissioner Sgt. Slaughter as he considered Goldust as a substitute for Helmsley. Helmsley regained the European title from Owen Hart on March 16th, 1998. The night after Wrestlemania XIV, Helmsley announced that Michaels had 'dropped the ball', and recruited a DX army consisting of the New Age Outlaws (Road Dogg & Billy Gunn) and X-Pac. During the summer of '98 DX feuded with The Nation of Domination (The Rock, D'Lo Brown, Mark Henry, & The Godfather). This lead to Triple H losing the European title to D'Lo July 14th '98 and eventually a 'ladder match' for the Intercontinental title, against The Rock, at Summerslam on August 30th, which Triple H won to reclaim the title for a second time. He was forced to vacate the title in October due to a knee injury that required surgery and put him out of action for a while.

At Wrestlemania XV, Triple H defeated Kane via disqualification. Triple H beat X-Pac at the 1999 Backlash. At Fully Loaded '99, Triple H defeated The Rock in a 'strap match'. The night after Summerslam, Triple H captured his first WWF title from Mankind on August 23rd 1999. He lost the title on September 14th to Vince McMahon who vacated the title six days later. Triple H reclaimed the vacant title at Unforgiven '99 on September 26th by winning the 'Six Pack Challenge' match featuring Mankind, The Rock, Kane, The Big Show, and The British Bulldog. At No Mercy '99, Triple H defeated Steve Austin. He lost the title at the Survivor Series on November 14th to The Big Show (Paul Wight) in a 'Triple Threat' match also featuring The Rock. Wight had substituted for the 'injured' Steve Austin who had been hit by a car earlier that evening. Triple H defeated WWF Owner Vince McMahon on December 12th at Armageddon when his daughter, Stephanie McMahon, turned on him and joined forces with Triple H. The McMahon-Helmsley era was born.

Triple H regained the WWF title for a third time by beating The Big Show on January 3rd, 2000. At the Royal Rumble on January 23rd, Triple H defeated Cactus Jack (Mick Foley) in a 'Street Fight'. At No Way Out on February 27th, Triple H beat Cactus Jack once more in a 'retirement' vs. WWF title 'Hell in a Cell' match, which meant Foley was forced to retire. Triple H defended the title at Wrestlemania XVI on April 2nd in a 'Fatal Four Way Elimination' match when Vince McMahon joined forces with the McMahon-Helmsley regime thus turning against The Rock. The match also featured a McMahon in every corner as Triple H had Stephanie, The Rock had Vince, The Big Show had Shane, and Mick Foley had Lynda McMahon who had persuaded Foley to compete in one more match. Triple H lost the title to The Rock at Backlash on April 30th. At Judgment Day on May 21st Triple H defeated The Rock 6 falls to 5 in a '60-minute Iron Man' match to capture his fourth WWF title. He lost the title back to The Rock at King of the Ring on June 25th in a six-man tag team match featuring Triple H, Vince, & Shane McMahon versus The Rock, The Undertaker, & Kane. Anyone gaining the pinfall would win the championship and The Rock pinned Vince McMahon. At Fully Loaded on July 23rd, Triple H beat Chris Jericho in a 'last man standing' match. Triple H defeated Kurt Angle at Unforgiven on September 24th in a 'no disqualification' match with Mick Foley as the special guest referee. On the November 6th RAW, Triple H attacked Steve Austin, revealing himself as the mastermind behind the hit and run incident at the 1999 Survivor Series. At the Survivor Series on November 19th 2000, Triple H faced Austin in a 'No DQ' match which ended in a no contest when Austin picked up Triple H in his car with a fork lift truck and dropped it 30 feet! At No Way Out on February 25th 2001, 'The Game' Triple H beat Austin in a 2 out of 3 falls match. Austin won the first fall. Triple H won the second fall, which was fought under 'street fight' rules. He then won the decisive fall, fought inside a steel cage, when each man hit one another at the same time knocking one another out and Triple H landed on Austin to gain the pinfall. At Wrestlemania X-Seven on April 1st, Triple H lost to The Undertaker. On April 3rd Triple H defeated Jericho for his 3rd Intercontinental Title. On April 10th he lost the title to Jeff Hardy, but regained it for a 4th time six days later. At Backlash on April 29th, 'The Two Man Power-Trip' Triple H & Steve Austin defeated 'The Brothers of Destruction' Kane & The Undertaker for the WWF Tag Team Championship. At Judgement Day on May 20th Triple H lost the IC title to Kane in a 'Chain' Match. The next night on RAW Triple H suffered a quadriceps tear in his left leg during a tag team match in which Austin & he dropped the title to Chris Jericho & Benoit. Shortly afterwards Triple H underwent surgery to repair the damaged leg.

After nearly eight months away, Triple H returned on the January 7th 2002 edition of RAW. At the Royal Rumble on January 20th Triple H eliminated Kurt Angle to win the battle royal and a title shot at Wrestlemania having been drawn no. 23. On the February 11th edition of RAW Triple H and Stephanie were scheduled to renew their 'wedding' vows, however Linda McMahon informed Triple H that Stephanie was faking her pregnancy. As a result, Triple H told Stephanie it was over between them, and gave Mr. McMahon a pedigree. At Wrestlemania X-8 on March 17th in Toronto, Triple H defeated Chris Jericho, who was accompanied by Stephanie, to win the WWF 'Undisputed' Championship (his 5th world title). On the March 25th edition of RAW Triple H defeated Jericho & Stephanie in a handicap match, which meant that Stephanie was forced to 'leave' the WWF. Triple H lost the 'Undisputed' Championship to Hulk Hogan at Backlash on April 21st.

At Summerslam on August 25th, Triple H lost an 'Unsanctioned' Streetfight to Shawn Michaels. On September 2nd Triple H was 'handed' his 6th World Heavyweight Title by Eric Bischoff, the General Manger of RAW. Because the WWE 'Undisputed' Champion, Brock Lesnar had signed an exclusive deal with SmackDown! Therefore the No. 1 contender, Triple H, could not face him for the championship and therefore Bischoff disputed the title and named Triple H as the RAW brands World Heavyweight Champion using the old WCW belt. Triple H lost the World Heavyweight Title to Shawn Michaels on November 17th in an 'Elimination Chamber' match at Survivor Series. However he regained the title the next month at Armageddon in a '3 Stages of Hell' match on December 15th. Triple H held the title for 10 months, eventually losing it to Bill Goldberg at Unforgiven on September 21st, 2003. He regained the title (his 8th) from Goldberg on December 14th at Armageddon. He lost the title to Chris Benoit in a Triple Threat match, also featuring Shawn Michaels, at Wrestlemania XX on March 14th 2004. On the March 22nd edition of RAW, Triple H was picked to go to SmackDown! in a 'draft lottery' only to be traded back to RAW for Booker T and The Dudley Boyz the very next day. At Unforgiven on September 12th, Triple H captured his 9th World title by defeating former Evolution member Randy Orton. On the December 6th edition of RAW, WWE Chairman Vince McMahon declared the title vacant and announced that Triple H was no longer the Champion following a controversial ending to a Triple Threat Championship match, also involving Christ Benoit and Edge, the previous week, in which Benoit forced Edge to submit but Benoit�s own shoulders were simultaneously pinned for a three count whilst Triple H was momentarily incapacitated outside of the ring. The following week, RAW General Manger Eric Bischoff announced that the World Heavyweight title would remain vacant until January 9th 2005, where the winner of an Elimination Chamber match, featuring Triple H, Edge, Benoit, Chris Jericho, Randy Orton and Batista, would be named the new Champion. At New Year�s Revolution, Triple H was victorious in the Elimination Chamber match and claimed his 10th World title. Triple H lost the title to former Evolution member Batista, at Wrestlemania 21, on April 3rd 2005.