WWE’s Best and Worst Main Events: Attitude Era Edition

Money poured into WWE during the Attitude Era. The shift in booking and story development toward a more risky, edgy product mirrored society. It was a bold move by WWE, but one that paid off immensely as the biggest stars and biggest box offices emerged from the era. The fans came out in droves, with arenas selling out all over the world. It became cool to be a fan of professional wrestling again.

Fans look back on the Attitude Era with fondness, but on a closer inspection, the match quality could have been better. The matches that main-evented Attitude Era PLE’s were very hit and miss in terms of their effectiveness. Yes, some have stood the test of time, but others held down the Attitude Era and are a black mark on its legacy. It was a varied era in terms of main events, and below we will look at the best and worst of these.

Best: Undertaker vs Shawn Michaels (Hell in a Cell Match; In Your House: Bad Blood 1996)

Anytime that HBK and The Deadman stepped into the squared circle, the world was presented with greatness. People look to WrestleMania 25 and 26 as examples of this, but one of their first encounters may be their best.

This was the first Hell in a Cell match, and it remains one of the best in company history. It revolved around Michael’s attempt to escape from The Undertaker, with the cage being lowered down to prevent this. Thus began an incredible cat-and-mouse game, with The Undertaker destroying The Heartbreak Kid at every turn.

This was violent and bloody, with great spots from start to finish. This match was perfect and remains the benchmark for every Hell in a Cell Match.

Worst: Undertaker vs Steve Austin (WWE Championship Match; SummerSlam 1998) 

The build-up to this massive showdown lasted the summer of 1998. Steve Austin and The Undertaker were the two biggest stars on the roster, and WWE put all its weight behind their WWE Championship showdown. Unfortunately, the match didn’t turn out like everyone had hoped that it would.

Whether it be through bad booking or lack of chemistry, there was something that didn’t work with this match. There were more botches than one would want out of a huge main event, and the finish ended with a whimper rather than fireworks. The expectation of what this match should have been did not live up to the actual contest.

Fans expected a fantastic match, but what we were given was something that would have been out of place on a weekly television show.

Best: The Rock vs Steve Austin (WWE Championship Match; WrestleMania X-7)

The Rock and Steve Austin were the preeminent stars of the Attitude Era. It was a rivalry against which all others were compared, and it was only fitting that their issues bookended the Attitude Era, closing out WrestleMania X-7. It was the biggest match featuring the two biggest stars of the era. Two babyfaces are going to battle with the crowd, ping-ponging their support along the way.

As expected, this match was fantastic. It included some great wrestling, but even better brawling as The Rock and Stone-Cold tore one another apart. Everything great about the Attitude Era was included in this match, with two icons doing whatever they could to win the WWE Championship.

We felt their desperation as they stooped to whatever level they could to get the victory. The ultimate finish was a risky one, but Steve Austin’s heel turn was the shock ending that this match needed.

Worst: Triple H vs The Rock vs Mick Foley vs The Big Show (WWE Championship Match; WrestleMania 2000)

The biggest argument for WrestleMania 2000’s failure was the massive overbooking of every match. The need to make every match a multi-man ruined the importance of every match, with the main event being the best example. It was a match featuring four men when, in essence, it should have been a one-on-one affair between Triple H and The Rock.

Adding The Big Show and Mick Foley to the match made little sense, and their inclusion didn’t make the match more exciting. They were the first two men eliminated and added nothing to the action. The audience was waiting for the two men to get out of the way so The Rock and Triple H could give them the show that they wanted.

It was a muddled mess with a terrible finish that saw Vince McMahon turn on The Rock to help Triple H retain the WWE Championship. No one wanted this match to start, or end, like this.

Best: Triple H vs The Rock (WWE Championship Match; Backlash 2000)

A month after WWE’s misstep, they righted the ship when they gave the world the main event that we all wanted, a one-on-one match between The Rock and Triple H. The Rock had been chasing Triple H for a few months, and despite the efforts of the newly minted McMahon-Helmsley regime, he finally got his singles opportunity.

The deck was clearly stacked against The Rock, and he valiantly fought off every crooked attempt by Triple H and his cohorts. The initial wrestling was great, but the fun really started when the action spilled out of the ring. The double-Rock Bottom spot was amazing, the run-in by Linda McMahon and Earl Hebner was perfect.

And of course, Steve Austin’s return was the pop that blew the roof off the arena. This was the match that should have taken place at WrestleMania, but at least we got it.

Worst: Triple H vs Chris Jericho (WWE Championship Match; WrestleMania X-8)

Everything about Triple H and Chris Jericho’s WrestleMania X-8 program was an abject failure. Jericho was never treated seriously as the Undisputed Champion, and he played second fiddle to the domestic issues between Triple H and Stephanie McMahon. It was embarrassing to see the reigning World Champion treated like a secondary in the build-up to a match where his championship was on the line.

These issues carried over into their WrestleMania main event, where we saw Stephanie McMahon take the focus away from the action in the ring. The wrestling was also not very compelling, showing little thought was put into the in-ring work.

This was the main event of WrestleMania, and it was merely a transition for McMahon/Helmsley to keep the attention on themselves. It also didn’t help that the crowd was exhausted from a match that should have gone on last.

Best: Shawn Michaels vs Steve Austin (WWE Championship Match; WrestleMania 14) 

The Attitude Era started with a bang when WWE produced one of the best main events, not just of an era, but of WrestleMania in general. It has been well documented that Michaels was dealing with back issues in the lead-up to this match, but you couldn’t tell from how he handled himself in the ring.

This was a wonderfully executed match with Steve Austin and Shawn Michaels. The crowd was in the palm of their hands, and it was a great example of how Attitude Era booking can be successful.

Naturally, this match is on this list for its result in addition to its wrestling. This was the turning point of WWE’s success. The Austin and Attitude Era began on this night as Stone Cold reached the top of the mount. WWE pulled ahead of the competition and never turned back.

Worst: Steve Austin vs Kane (First Blood Match for the WWE Championship; King of the Ring 1998)

The Attitude Era was full of matches where the bookers threw everything at a wall and saw what stuck. Sometimes it worked, other times it blew up in WWE’s face.  This main event was one of the times when things blew up.

Steve Austin taking on Kane was a match with a no-win scenario. Austin had just begun a reign with the WWE Championship and was more popular than ever. Kane was still taken seriously as a monster and couldn’t afford to lose. It made no sense to have them do battle for the WWE Championship, where neither man could afford to lose. WWE’s workaround was a cheap way to end the match and the PLE. They booked themselves into a corner, and no one was happy with the result.