WWE began to flex their muscles in 1999 with WCW on a downward spiral. Despite 1999 being a successful year for WWE, some nonsensical moments occurred in that year.
1999 was another transitional year for WWE with many new talent emerging and some leaving the company. The Attitude Era was arguably the greatest period in WWE history with the amount of top-level talent that WWE had at their disposal. Moreover, most WWE Championship title changes happened in 1999. Unfortunately, Stone Cold Steve Austin who was the undisputed face of WWE his neck issues resurfaced which forced him to the sidelines.
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Nevertheless, Triple H became a legitimate main eventer, The Rock and Mankind's rivalry at the start of 1999 was amazing, The Undertaker was a full-fledged heel, and SmackDown was born. WWE unquestionably had a plethora of memorable moments in 1999, but some things failed to add up.
10 Bart Gunn Facing Butterbean At WrestleMania XV
Bart Gunn tore through the field in the Brawl For All tournament in the summer of 1998. However, the former Smoking Gunn would have thought that his triumph would have seen him propelled further up the card.
That failed to materialize, and he cut his long hair short and collided with Butterbean at WrestleMania XV. This was not a wise decision as Bart believed his own hype, and he was brought back down to Earth by Butterbean. Bart never recovered from this loss as he got humiliated by Butterbean in seconds and was clearly out of his depth.
9 Vince McMahon Not Cancelling Over The Edge
"The Show must go on" is a phrase that is commonly heard in professional wrestling when a tragedy occurs. At Over The Edge, Owen Hart was portraying The Blue Blazer and he was supposed to descend from the rafters in his Intercontinental Championship match with The Godfather.
Sadly, the stunt went wrong which resulted in Owen passing away. Jim Ross and Jerry "The King" Lawler did a remarkable job on commentary, and they were clearly shaken by the news of Owen's passing. The show continued with Undertaker dethroning Steve Austin for his third WWE Title reign in the main event. It was logical for the pay-per-view to be stopped after this horrific tragedy.
8 Triple H Not Winning His First WWE Title At SummerSlam
Stone Cold Steve Austin defended the WWE Championship against Triple H and Mankind in a triple threat match at SummerSlam. Jesse Ventura oversaw proceedings as the special guest referee. This was a decent triple threat match with all three men putting on a good performance.
However, Triple H was yet to taste WWE Championship gold but for whatever reason, Austin did not want to lose the title to The Game. That's why Mankind earned an unlikely third WWE Title reign. His championship reign was short-lived as Triple H won the title just 24 hours later on Raw. While it was Triple H's crowning moment, it was logical for Triple H to win the title at SummerSlam which was a marquee event.
7 Non-Wrestlers Winning The Women's Championship
Women's wrestling was a laughing stock in the Attitude Era so it was not shocking when the wrong talent held the championship. However, it still made no sense for the likes of Debra and The Kat to hold the Women's Championship in 1999.
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Thankfully, Ivory had a decent run with the title when she won the championship a couple of times in 1999. She could have had a lengthy program with Jacqueline to legitimize the title, instead of it being a prop when Debra and The Kat had underwhelming runs with the title.
6 Buried Alive Match On SmackDown
The WWE Tag Team Championship was like a hot potato and many main-event level talents held the titles. On the September 9, 1999, edition of SmackDown, The Undertaker and Big Show challenged The Rock 'n' Sock Connection in a tag team Buried Alive Match for the WWE Tag Team Titles.
Buried Alive matches are extremely rare but for one to take place on SmackDown, it seemed random. Triple H got involved in proceedings but Undertaker and Big Show reclaimed the titles. It didn't need to be a Buried Alive match, which should have been reserved for a bigger show.
5 Corporate Ministry
The Undertaker's Ministry of Darkness stable feuded with Mr. McMahon's Corporation faction for the first few months of 1999. They would trade blow for blow in a power struggle despite both factions being heels.
However, on the pilot episode of SmackDown on April 26th, the two factions fused to become The Corporate Ministry. They were one of the most powerful entities but it was illogical for The Ministry of Darkness and The Corporation to merge. Both factions had enough to function on their own, and it went downhill when they were together.
4 Mankind Taking Brutal Unprotected Chair Shots To The Head
It was quite predictable that The Rock and Steve Austin would be on a blockbuster collision course for the WWE Championship at WrestleMania XV. Meanwhile, Rock and Mankind had one of the best rivalries in the Attitude Era over the WWE Championship before WrestleMania happened.
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Once again, they took their feud to the next level in an I Quit match for Mankind's WWE Title at Royal Rumble 1999. They tore the house down once again but Rock delivered 11 unprotected chair shots to Mankind's head. There was no need for that number of chair shots, considering Foley's family was in attendance and it gave violence a whole different meaning.
3 Kennel From Hell Match
Big Boss Man and Al Snow are amongst the greatest Hardcore Champions of all time. They traded the title in two pay-per-view matches at Fully Loaded and SummerSlam. However, they contested one of the worst matches in WWE history at Unforgiven.
Their Hardcore Title encounter was a Kennel From Hell match which was virtually a Hell in a Cell match and another cage placed inside it. There were dogs on the outside which were not properly trained as they defecated all over the place. The whole stipulation was a mess and never should have happened in the first instance.
2 Undertaker Hanging Big Boss Man
The early stages of The Undertaker's WrestleMania unbeaten streak weren't the greatest. Undertaker represented The Ministry of Darkness, and he squared off with The Corporation's Head of Security, Big Boss Man in a Hell in a Cell match at WrestleMania XV.
The match was dreadful from start and finish with a little color being added to the match. Undertaker was barely in trouble and prevailed with a Tombstone Piledriver. However, the aftermath was memorable with Undertaker hanging Boss Man with a noose that was handed to him by The Brood. The whole angle was illogical especially since Boss Man showed up on TV the next night.
1 Mr. McMahon Winning The Royal Rumble Match
The 1999 Royal Rumble match was simply about Mr. McMahon and Stone Cold Steve Austin. They were the first two entrants in the Rumble match but they spent a large amount of time outside of the ring.
Nevertheless, they resurfaced in the latter stages of the Rumble, and with some assistance from The Rock, McMahon stunned Austin to win the Royal Rumble match. McMahon winning the Rumble was truly shocking but he was never going to headline WrestleMania. Austin should have gone over and handed McMahon his comeuppance as he went on to main event WrestleMania anyway.
