By 1996 Hulk Hogan, Ultimate Warrior, Ric Flair, Randy Savage, Razor Ramon, Diesel and Yokozuna had all left the WWE. As the only remaining multiple-time WWE World Heavyweight Champion Bret Hart had to take over the top spot in the WWE. Bret Hart would have a lot of new contenders for his WWE World Heavyweight Title though.
The Heart Break Kid
Bret Hart’s number one challenger was Shawn Michaels. Shawn Michaels went to the 1996 Royal Rumble and won for the second straight year. The match that would follow at Wrestlemania was one of the greatest matches of all time. Bret Hart and Shawn Michaels would wrestle in a sixty minute iron man match that would end in a 0 – 0 tie. It was decided that the match would go into overtime with the next pinfall winning the match. Shawn Michaels then pinned Bret Hart to become the WWE World Heavyweight Champion.
After successful defenses against Mankind, Vader and the British Bulldog, Shawn Michaels carried on with his title reign. It wasn’t until his match with former bodyguard, Sycho Sid, that Shawn Michaels would drop the belt. At the following Royal Rumble Shawn Michaels would win the title back.
At the 1997 Royal Rumble a new number one contender was supposed to be crowned. Bret Hart eliminated Steve Austin but the officials didn’t see the elimination. Steve Austin then re-entered the ring and eliminated Bret Hart, the Undertaker and Vader. After the videotape was reviewed it was clear that Steve Austin was eliminated and that he illegally eliminated the other three. Therefore Bret Hart, Steve Austin, the Undertaker and Vader would fight each other in a fatal four way match.
Bret Hart was supposed to win the Fatal Four way match and then win the WWE World Heavyweight Title from Shawn Michaels at Wrestlemania 13 but Shawn Michaels refused to. Instead Shawn Michaels announced he was taking time off because he “lost his smile” and he was stripped of the WWE World Heavyweight Title. The Fatal Four way then became a title match and Bret Hart won the WWE World Heavyweight Title. The very next night Bret Hart would lose the title to Sycho Sid due to interference by Steve Austin.
Going into Wrestlemania the card was set to have Sycho Sid defend his belt against the Undertaker while Bret Hart took on Steve Austin. The week before the PPV Bret Hart and Sycho Sid had a title match. If Bret Hart had won he would’ve won the title and his match with Steve Austin would be the WWE World Title match. If Sycho Sid won he would keep the title and the match with the Undertaker would be the World Title match. The WWE decided to let Sycho Sid retain the title and he went on to lose the title to the Undertaker in one of the worst Wrestlemania matches of all time. Meanwhile, Steve Austin and Bret Hart had one of the best matches of all-time.
The win over Steve Austin made Bret Hart the number one contender and he would get a title match against the Undertaker at SummerSlam 1997. Bret Hart’s rival Shawn Michaels was the guest referee so many expected foul play but Shawn Michaels promised to call the match down the line. During the match Bret and Shawn got into an argument and Shawn tried to super kick Bret. Bret Hart dodged the super kick and Shawn Michaels kicked the Undertaker instead. Bret then covered the Undertaker and Shawn Michaels, wanting to prove he was fair, begrudgingly counted to three and crowned Bret Hart the five-time WWE World Heavyweight Champion.
The WWE was having some financial problems and Bret Hart was forced to sign with WCW. Bret Hart would first have to drop the title to Shawn Michaels at Survivor Series 1997. Bret Hart refused to lose the match in his home country and instead wanted to lose the title later. Vince McMahon couldn’t risk letting Bret Hart end the show with the WWE World Title though because his contract was up and he could take the title to WCW if he still had it. Instead Vince McMahon rang the bell in the middle of the match, saying that Bret Hart had tapped out when he never actually did. The match is notoriously known as “the Montreal Screwjob.”
At the 1998 Royal Rumble Shawn Michaels faced the Undertaker in a Casket Match. Shawn Michaels was dropped onto the casket and herniated two discs in his back. Shawn Michaels was forced to retire but he would go out in style wrestling one last match against Steve Austin at Wrestlemania. Shawn Michaels took his usual bumps despite the injury and put over Steve Austin. With the World Heavyweight Title win by Steve Austin the Attitude Era would begin and “Stone Cold” Steve Austin would take over the WWE.
Steve Austin was an anti-establishment champion and his feud was with WWE owner Vince McMahon. Vince McMahon acquired the services of Kane and the Undertaker to try and win the WWE World Heavyweight Title. Kane would be the first one to defeat Steve Austin, though he defeated him in a First Blood match and never actually pinned Austin. Steve Austin would get a rematch against Kane the next night since he argued he never got pinned and Austin won the World Heavyweight Title back.
The Brahma Bull
Later Steve Austin took on Kane and the Undertaker at the same time in a three-way match. Kane and the Undertaker both pinned Steve Austin simultaneously and it was decided the title would be held up. At Survivor Series 1998 a 13-man tournament was held to crown a new WWE World Heavyweight Champion. In the Quarterfinals the Undertaker and Kane were paired up with each other and the Undertaker came out victorious. The Undertaker would go on to face the Rock, where he would lose by DQ. Meanwhile Steve Austin was defeated by Mankind to make the finals The Rock versus Mankind. The Rock defeated Mankind to win his first WWE World Heavyweight Title.
Mrs Foley’s Baby Boy
Mankind thought that Vince McMahon was manipulating the Survivor Series tournament in order to help him win but Vince turned on Mankind in the Finals when he helped The Rock win. Mankind then became the second biggest face in the company and feuded with Vince McMahon and his Corporation. On December 29th, 1998 Mankind finally defeated The Rock to win the WWE World Heavyweight Title.
In 1999 the WWE World Title changed hands more than any other year. The title bounced from wrestler to wrestler eleven times in ten months. The first title change came at the Royal Rumble where the Rock fought Mankind in an “I Quit” match. The Rock hit Mankind with a chair a dozen times but Mankind never said “I Quit”. The Rock won when he had someone play a recording of Mankind saying “I Quit” to win the match. Later that month Mankind got a rematch against The Rock during the halftime of the Super Bowl. The match was a No DQ Fall Count Anywhere Match and Mankind used a forklift to pin down The Rock and win the World Title. The Rock would win the title back once again in a Ladder Match in February.
The Rock would then move on to a feud with Steve Austin, which would culminate at Wrestlemania XV. Stone Cold would come out victorious to win the WWE World Heavyweight Title for a third time. Steve Austin would enjoy the longest title reign of the year, almost two months. The Undertaker would win the title from Steve Austin but Steve Austin would win it back one month later.
The Cerebral Assassin
If The Rock, Stone Cold, The Undertaker and Mankind weren’t enough, Triple H was also added to the main event picture. After another near two-month reign for Steve Austin he took on Mankind and Triple H in a triangle match. Mankind would come out victorious but Triple H would defeat him the next night on Raw to win his first WWE World Heavyweight Title.
There would be another contender for the World Heavyweight Title in September, the WWE owner himself, Vince McMahon. Vince McMahon would defeat Triple H and then vacate the title and booked a six-pack challenge for the vacant title. In the six-pack challenge Triple H would once again be the winner. The World Heavyweight Title picture got yet another contender when The Big Show closed out 1999 with the WWE World Heavyweight Title after beating Triple H and The Rock in a Triple Threat match.