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Rockaustinxix
March 10, 2026 By  History, WWE, WWE Universe

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.

About Daniel Sinasac

Dan has been a fan of wrestling since his grandmother sat him down to watch JYD and Sgt. Slaughter go to battle. That began a decades-long obsession with professional wrestling. An obsession that has developed into a love/hate relationship with the greatest entertainment medium in the world.

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