Date: January 11, 1999
Company: WWF
Show: Monday Night Raw
Rules: Royal Rumble
Stipulation: Winner gets the #30 spot in the 1999 Royal Rumble
Roster (10): The Big Boss Man, Chyna, “Bad Ass” Billy Gunn, Kane, Vince McMahon, Road Dogg, Ken Shamrock, Test, Triple H, X-Pac

Ah, the late 90’s. The Attitude Era. The Monday Night Wars. A golden age of talent, even though Vince Russo was the guy writing the show. Swerves and over-booking all over the place during his latter days in the WWF. That’s the main reason why I consider the ’99 Royal Rumble to be the “least best” Rumble in that it’s just too busy. But hey, at least it’s better than the mini-Rumble that precedes it.

Vince McMahon has been stuck in his highly-successful feud with Steve Austin, not to mention a side-feud between his Corporation and the stable D-Generation X. McMahon made sure that Austin’s role in the Rumble would be automatically at #1 and penciled himself in at #30 to make sure Austin had no chance in Hell. Commissioner Shawn Michaels finagled with that idea and made it so that McMahon would be #2.

Amidst this big Corporation/DX feud, McMahon decided to put together a Corporate Royal Rumble. A smaller-scaled Rumble featuring only members of both stables where the winner would earn the #30 spot. We know we’re in for some bad times once we see that Shane McMahon is doing commentary.

If you’ve never experienced it, Shane’s commentary is as bad as his punches.

We’re off to a wonderful start when Corporation member Ken Shamrock eliminates himself immediately by jumping over the top rope to get at entrant #2, Billy Gunn. It isn’t a total loss of logic, as Shamrock spends the next minute or so beating the crap out of Mr. Ass, slamming his head into the steps repeatedly until the Big Boss Man is out next. Shamrock leaves and allows Boss Man to continue the beating. At #4, the New Age Outlaws theme plays, but it’s Test who runs out to help out Boss Man. Whoops.

Things finally start to go DX’s way slightly when X-Pac comes out. Then Test eliminates Gunn and we’re back to square one. Road Dogg comes out to even the odds, but then Kane – representing the Corporation – puts it back in their court, eliminating Road Dogg and making it 3-on-1. Triple H runs out next and while he’s overwhelmed, he still tricks Test into clotheslining Kane, who doesn’t budge, but isn’t very happy.

The ring gets cleared until it’s just Triple H vs. Boss Man. On paper, we have all of our announced entries, but then Vince McMahon comes out as #9 and causes Triple H to stop working on Boss Man. Boss Man gets up and the two grapple near the ropes. Vince rushes in and eliminates both at the same time. Boss Man is confused at first, but then celebrates his boss’ victory.

Vince is happy because he’s cheated the system. Now he’s #30! …Or is he?

Chyna comes out last, showing that DX also has some surprises in store. Patterson and Brisco try to prevent her entry, but she takes a swing at both. We don’t get any real Vince vs. Chyna battling as Steve Austin walks out for the sake of getting in Vince’s face. Vince is distracted by this and Chyna takes advantage.

Chyna wins a spot as the first woman to enter the Royal Rumble, doing so at #30. It didn’t really do her much good. In the Rumble itself, she eliminated Mark Henry and then Austin immediately threw her out. The whole thing was a convoluted mess that ended with Vince McMahon winning at #2 and Austin getting the Wrestlemania title shot anyway.

That’s what you get when you play with Russo. Speaking of him, the next update is another one of his babies, only off in WCW. Come check it out.