Shawn Michaels

Shawn and the Undertaker wrestled to a no contest at IYH: Ground Zero, which set up the first ever Hell in a Cell match at IYH: Badd Blood. Before that match took place, Shawn won the European title from the British Bulldog at One Nite Only in England. Shawn won the brutal cell match with the Undertaker due to interference from Kane. At the Survivor Series, Shawn made Bret Hart submit to his own hold, the Sharpshooter. He won his third WWF title, which he defended against Ken Shamrock at IYH: D-generation X. He lost by DQ, and shortly thereafter, Rude went to WCW. Shawn lost the European title to Triple H in a faux match, which was ordered by Sgt. Slaughter. Michaels simply laid down, and Triple H mocked the Ultimate Warrior by running around the ring and then pretending to splash Michaels for the pin.

Shawn then won a Casket Match against the Undertaker at the Royal Rumble, again, because of interferece from Kane. He finally lost the WWF title to Steve Austin at WrestleMania XIV, injuring his back in the process. The back injury turned out to be career-ending. Shawn returned months later to be the WWF's Commissioner, but once he got married, he chose a family life over wrestling. He started his own promotion in San Antonio, and wrestled his retirement match on April 4, 2000.

He returned to WWE full time in May of 2002, as an advisor to the nWo, headed by his friend Kevin Nash. He tried to recruit Triple H to their side, but the nWo disbanded after Nash tore a muscle in his leg, putting him out for an indefinite period of time. When Raw and Smackdown got GMs, they both tried to sign Triple H to their side. Michaels persuaded HHH to join Eric Bischoff on Raw, but was upset when HHH named him as a manager. Triple H told him not to worry, and they returned later that night, clad in DX shirts. However, as Triple H did his old mic routine, he suddenly turned on Michaels and gave him a Pedigree. The next week, HHH was explaining why he turned on Shawn when a stagehand informed him that Shawn had been put through the window of a car in the back. HHH was remorseful and vowed to find out who did it. The next week, Shawn appeared on Raw from his home, and showed everyone some footage that showed a security camera catching Triple H attacking him. HHH admitted to the crime, and said it was to protect Shawn, to show him he was too vulnerable to get in the ring with him. Shawn broke his retirement by challenging HHH to a streetfight at SummerSlam. Shawn's return was triumphant, but HHH attacked him after the match with a sledgehammer. Shawn was stretchered out and didn't appear again until October, where he revealed that his rehab was complete and he was coming after HHH. He returned at Survivor Series, against HHH, Booker T, Rob Van Dam, Kane and Chris Jericho in the first ever Elimination Chamber match for the World Title. He won the match and the title, but HHH was relentless, and defeated Shawn in a Three Stages of Hell match at Armageddon to win the title back.

Shawn was confronted the next night by Chris Jericho, who said he no longer had any respect for Shawn. He told Shawn to prove that he was still the same HBK that drew number one in the 1995 Royal Rumble and volunteer for the number one position in the 2003 Royal Rumble. Shawn did so, and Jericho subsequently won a match that gave him the right to choose his number for the match. Instead of going for number thirty, Jericho chose number two. He eliminated Shawn quickly, with help from Christian and a steel chair. Shawn caused Jericho to be eliminated later on, and continued to plague Jericho. They met at WrestleMania XIX, with Shawn picking up the victory. He teamed with Kevin Nash and Booker T to lose to Triple H, Ric Flair and Jericho at Backlash. He supported Nash in his chase for HHH's World Title until after Judgment Day. When Triple H could choose any challenger he wanted, he chose Flair so that he could lay down for him. Shawn convinced Ric that he could take the title, and the next week requested a match against him to see how high he was on the Ric Flair measuring stick. Flair accepted, but GM Eric Bischoff made the match a handicap match, with Flair and Shawn teaming against HHH. Flair turned on Shawn during the match, showing that he still was the same old Flair. Shawn met Flair at Bad Blood, and lost. He then became the target of Randy Orton, who fashioned himself a Legend Killer after beating down Mick Foley. He cost Shawn a rematch with Jericho, and both men were entered into an Elimination Chamber match at SummerSlam for the World Title. However, both were defeated by Goldberg in the match. They finally met at Unforgiven, and Orton won after Flair handed him some brass knuckles. Shawn was chosen by Steve Austin to be the last member of his Survivor Series team. If Shawn's team lost, then Austin would be fired as co-GM of Raw. Shawn teamed with RVD, Booker T, and the Dudley Boyz to take on Jericho, Christian, Scott Steiner, Mark Henry and Randy Orton. Shawn was the last member on his team against Jericho, Orton and Christian. Shawn managed to pin Christian and Jericho, but Orton pinned him thanks to Batista. Shawn confronted Batista the next week, and they had a match at Armageddon. Shawn pulled a superkick out of nowhere and managed to beat the big man.