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Why this was the Best Storytelling for a Royal Rumble Match

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The ‘99 Rumble match wasn’t great but the story leading up to it was dope.

WWE

The Royal Rumble sells itself. That’s usually the thought in circles of people who talk about what happens in the squared circle. Seeing multiple contestants form alliances, test friendships, and do whatever it takes for a shot at the heavyweight champion is compelling. WWE took a different approach in 1999.

You see the main image so you know where this is going, but the 1999 Royal Rumble is not only the best build to a Rumble match up to that point, but it hasn’t been topped since.

Storytelling should be simple. You take your bad guy, McMahon, and have him throw everything possible at your good guy, Austin. WWE excelled at that for pretty much all of 1998 as Vince did all he could to make Austin the next former heavyweight champion of the world.

Once McMahon found a guy not averse to shaking hands and kissing babies in The Rock, the story went to a different level; McMahon was now on defense.

Vince knew the Royal Rumble was the one chance Austin had at getting back into the title picture. Austin won the Rumble two years in a row, so the odds were in his favor he’d get the hat trick and be on the opposite side of the ring against the corporate champ at WrestleMania 15. At that point, WWE did the best thing any storyteller can do: raise the stakes.

The second act of any good story puts the protagonist in an even worse position than before. If the first act finds them in a tree with no way to get down, the second lights said tree on fire. Once McMahon made Austin the first entrant into the Rumble and put a $100,000 bounty on his head, it felt more like igniting a flamethrower on a whole forest, much less one tree.

When the boss is willing to give six figures to the man who takes the Texas Rattlesnake out of commission, it builds on a few aspects of WWE continuity: the sheer insane number of people Austin more than rubbed the wrong way since ‘96, McMahon’s willingness to throw money at any problem since he was “outed” as the owner, the proliferation of factions since ‘97 meaning everyone but Austin has someone watching their back, and the fact the company relied less on old school ideals of good guys and bad guys.

Whether it was a member of DX or a member of The Ministry of Darkness, the line between good and evil was so thin it was practically emaciated. Putting money on Hogans’s head in the ‘80s would’ve invited the usual suspects. In contrast, the good guys would’ve refused on principle or even helped him. In ‘99? Not so much.

Every story needs a wrinkle or two, even if the audience sees them coming from 10 miles away. Was it obvious McMahon would be the number two entrant into the Rumble once he declared himself eligible? Of course. Was it the right thing to do? Also, of course. Throw in the fact Austin couldn’t even lay a pinky toe on the chairman until the Rumble match, and WWE had all the ingredients for a volatile powder keg.

WWE

The audience wanted nothing more than to see Stone Cold get his hands on the company’s biggest heel. Every week on Monday Night Raw, McMahon’s dastardly deeds only increased their bloodlust. McMahon needed to go down, and Austin had to be the one to do the honors.

But it wouldn’t be easy.

Austin dealt with a target on his back, a number one entry, Superstars openly preying on his demise, and the Corporation as a whole. But the biggest issue was Austin himself. Would he let his hatred for Vince distract him from getting a spot in the main event at WrestleMania? Would he have so much fun toying with Vince that he’d lose focus? And lastly, Austin needed to decide if the WWF World Heavyweight Championship was more critical than stomping a mudhole in Vincent Kennedy McMahon and walking it completely dry.

The match itself left a lot to be desired, which is to say it’s less than dope. One could argue a staple of the Attitude Era is stories with a great setup leading to a payoff of meh proportions. Luckily, we’re here to talk about everything before the match, and in that regard, this is a home run.

Everything about the Austin and McMahon rivalry went to 11. More groundwork was laid for the first of three Mania matches between Austin and The Rock, and seeds of dissent were sown within several groups. Like any good story, it was so much fun to watch.