Event: Royal Rumble 1999
Date: January 24, 1999
Location: Arrowhead Pond in Anaheim, California
Winner: Vince McMahon
Last Eliminated: Stone Cold Steve Austin
Iron Man: Vince McMahon
Quickest Out: Gillberg
Most Eliminations: Stone Cold Steve Austin
After a really fun Rumble the year before, the WWF followed up with one of its worst booked matches in history. That's overall, let alone for a Rumble match, which is pretty hard to fuck up.
The story was once again all about Stone Cold but this time it centered around his rivalry with the Chairman of the Board, Vince McMahon. Right away, the two were in the ring after drawing numbers one and two but that didn't last long. No, one of them didn't get eliminated, they just up and left the ring through the ropes -- not over them, of course -- and disappeared to the back, brawling all the way.
Austin ended up beaten up and taken to the hospital by McMahon's cronies, The Corporation, and Vince just hung around for a while before returning ringside way later in the match to do commentary. Austin, of course, eventually made his way back after hi-jacking an ambulance and eliminated more wrestlers than anyone else, despite hardly spending any time in the actual ring. He did a lot of this, mind you, while McMahon was at commentary.
Naturally, they were the final two and Austin had to hop out of the ring again to grab Vince and put him in the ring to commence the beat down and inevitable toss out. But The Rock came down to distract Austin and, like a total donk, he went for it, allowing McMahon to eliminate him to win the Rumble.
Yes, Vince McMahon winning a Royal Rumble match. Just awful.
As for the parts in between all that, when the two weren't in the ring, there is very little to say about all that. There were multiple dead spots in the match, with wrestlers in the ring just standing around waiting for the next entrant, and there were far too many jobbers who presented no real threat to win. A total of six of the 30 entrants spent less than a minute in the match, Mabel was eliminated because he was kidnapped, and Kane eliminated himself.
This entire match was just awful.