Man, terrific question. Ok, the show would have to be Wrestlemania for me, at Madison Square Garden, with the announcers being Gorilla Monsoon and Bobby Heenan. At first, I was tempted to put Gordon Solie with the Brain, but then I realized that Gordon Solie wouldn't play as much a foil to the Brain as Gorilla did, so the team of Solie and Heenan would lose a bit of its luster.
1st Match: Andre the Giant V.S. The Undertaker
To the best of my knowledge, such a match has never happened, and it's always been my dream match. Imagine the aura combined by these two. It would be an outstanding clash of the titans, and quite frankly, I'm not sure if I could pick a winner too well. I guess if I had to pick, I'd say the winner would be Taker, but it just seems like a battle between two legends whose shadow will loom over the WWE for a long time to come.
2nd Match: Tag Team Tornado Bullrope Match:
Cowboy Bob Orton & Randy V.S. Dusty Rhodes & Dustin
This may be a little below Dusty to do, but my thought is simple. Take two of the best father-son teams, latch father and father together (as well as son and son), and watch them go. This is one of Dusty's best kind of matches, it works into Bob Orton's gimmick extremely well, and Randy and Dustin will be sure to hold their own. Hell, they're going to have two rings (more on that in a couple matches) to work with. Maybe as soon as one member of a team beats the other, he goes over to help the other partner.
3rd Match: Tag Team Ladder Match:
The Midnight Express V.S. The Rock and Roll Express V.S. The Hardys V.S. Edge and Christian
I think people forget just how good the Rock N Roll and Midnight Express truly were. They would work pefrectly in a match like this, and we all know this is match made for the Hardys and E&C. Put these four teams, with classic rivalries added to each team, together with a ladder, and watch them go.
4th Match: Mr. Perfect V.S. The Rock
A match that is destined to give us classic memories. Two cocky legends going at it, in what should be an incredible match
5th Match: Ultimate Submission Match (30 Minutes)
Bret Hart V.S. Kurt Angle
Yes, I'm folding and typing a match that everyone else is thinking of. This would be a barnburner, as you have the best technical wrestlers of all time working against each other. Could be an instant classic.
6th Match: Wargames
The Four Horsemen (Flair, Arn, Tully, and Barry) V.S. D-Generation X (Shawn, Triple H, Road Dogg, Billy Gunn)
I know, this really pigeon holes Ric and Shawn, but I think this match can be just as good as any of the matches I could come up with either of the two. You have two teams that defined their era, and you put them into WarGames? Tell me that doesn't sell itself. Besides, this is my dream, right? Besides, if you really want to, you can have J.J. Dillon and Rick Rude outside of the ring (You never said that wrestlers couldn't come back as mangers)
7th Match: Fatal Four Way
Jake the Snake V.S. Roddy Piper V.S. Chris Jericho V.S. Eddy Guerrero
Can you imagine the mic work between these four leading up to the pay per view? Did you see the promo between Piper and Jericho last Monday? This could be another instant classic. Just make sure Jake is good before he makes it to the show...
8th Match: Four Way Tag Team Match
The Outsiders V.S. Demolition V.S. The Road Warriors V.S. The Steiners
These are the tag teams that are classic teams, but just would not work well in a ladder match. This would be an elimination match, and simply these teams would brawl and brawl and brawl and brawl.... And maybe Scott would pull a Frankensteiner.
9th Match:
Macho Man Randy Savage V.S. Kenta Kobashi
Kobashi just never has a bad match. Never. As a matter of fact, all he has is exemplary matches that if someone from the states were to ever watch, they would see greatness. these two, working against each other in a match? This should have been the match presented for the Macho Man at Starrcade 1995. If only WCW made its deal with All Japan, and not New Japan. Sigh....
10th Match:
Jushin Thunder Liger V.S. Rey Mysterio
This is a match that has actually already happened, and I know this. But it was so good, and from what I understand, it was not Liger at his best. Both of them, in their prime, one more time.
11th Match:
Stone Cold V.S. Hulk Hogan
Do I really need much of an explanation? This is THE dream match. End of story. End of pay per view.