So I've read all 4 pages of this thread and I've come to the conclusion that I have to be *that* guy. The guy who actually wants to see this match, that is. In fact, a friend and I were just discussing how said match can and should be booked. I see it playing out as follows:
Step 1: Replay Royal Rumble 1991 (1992?) where Flair won the belt. Obviously, several components will have to be changed that would suite the storyline. The winner will still get the title shot at WrestleMania instead of winning the belt as Flair did. Also, Hogan will have to enter near the end of the Rumble - thereby heightening the suspension of disbelief that Hogan can (and should) be perceieved as a threat. This, too, can be conveyed in a storyline touting Hogan's vast array of accomplishments, including his two consecutive Rumble victories.
Let me take a quick detour from my fantasy booking to chatise you young whippersnapers for a moment. Those of you condeming the proposed match/angle based on a lack of - wait for it - realism, really ought to have your heads examined. I've got to believe that this is coming from the 20 and under club. In this theater of the absurd that is professional wrestling that we love so dearly, we're lead to believe that Hornswoggle could defeat both The Miz and Jamie Noble, a 5'8" Shawn Michaels can defeat a 7'0" 305 lbs. Kevin Nash, The Undertaker and Mark Henry, "The World's Strongest Man." I've said this countless times and I'll say it again - if you've tuned into wrestling because you want realism, you're barking up the wrong tree. That's what boxing, MMA and other combat sports are for. Actual wrestling is secondary to the storyline. Always has been, always will be. And for good reason. A very old, very wise, very successful man by the name of Jim Barnett once said "The angle is the dangle that heats the meat!" He could not be more spot on in his analysis. Yes, the culmination of the angle should be well executed, psychologically engaging (key term - write it down) "wrestling" match. That means you don't need a series of disjointed flippity flopping to convey your story to audience.
Hulk Hogan knows a thing or two about captivating an audience. And for those of you who may question the appeal of Hogan in a wrestling match to the lay fan, you need only look back a few years to Flair's send off at WrestleMania 24. When booked properly, nostalgia draws - and draws big.
Anyway, I digress. Back to fantasy booking:
In the Rumble match, have him enter at the 29 spot after the ring has been all but cleared, save for Punk, Del Rio, perhaps Ryback and maybe Sheamus. Hogan comes out to a thunderous ovation, and makes his way down the aisle. They mix it up with the Hulkster, who need not bump all that much to sell taking a beating. Then, it happens - the gong. Turns out The Undertaker, who announced his retirement after this 'Mania, set his sights on reconciling his Streak with going out as WWE/WHC. So, The Undertaker now takes aim at clearing an already sparsely populated ring. 'Taker eliminates Del Rio and Sheamus in short order, leaving Punk, Hogan and 'Taker. Have 'Taker eliminate Hogan - leaving a frustrated Hogan standing next to the ring, hand on his hips, looking dejected. Hogan could extend his hand to an onlooking Undetaker, leaving CM Punk, always the opportunist, to dump The Undertaker over the top rope. You've effectively set up an epic encounter between two iconic figures in "The Immortal" Hulk Hogan and The Undertaker. You've also established CM Punk as you're #1 contender, which essentially assures you a phenomenal WWE/WHC match for WrestleMania (especially if it's against John Cena).
Step 2: The actual match itself at Mania is a a breeze to book. I envision it as a "No Holds Barred"-type of match. This eliminates the need for huge spots inside the ring. Hogan could easily take a ring post, get a little color and have the crowd eating out of the palm of his hands. The match will not be filled with big bumps or false finishes. In fact, I can only think of two times where I would employ a false finish. Towards the end of the match, as they're about to go home, 'Taker hits the Tombstone. He crosses Hogan's arms, sticks his tongue out as the ref counts 1-2 - and just as his hand nearly reaches the mat, Hogan miraculously pops up. To his knees at first, his eyes wide and chest billowing breathes from deep within his lungs, he makes his way to his feet as the 'Taker heaps on those MMA-style jabs, all to no avail. Hogan marches around the ring as 'Taker follows, hitting him in vain. Then, it comes - "YOU!" Hogan begins mounting an attack, stunning the big man, throwing him into the ropes for the Big Boot. Hogan, mustering every last ounce of the spirit of Hulkamania, bounces off the rope for the Atomic Leg Drop. Cover. 1 - 2 - shoulder up. The Undertaker, like so many times before, sits up to a seated position. Hogan, near tears, realizes the end is near. After a short back-and-forth, Hogan takes a second Tombstone and is pinned, essentially closing out the WrestleMania chapter of both he and Hulk Hogan's respective careers.
So, long story short, would I like to see it? I get goosebumps WRITING about it, so I could only imagine that unforgettable encounter actually playing out with two people who are the caliber of performers that The Undertaker and Hulk Hogan are.
You can hurl insults my way for being a nostalgia mark. And perhaps you're right. Maybe I am a mark for the era I grew up watching. But I'd like to think J.J Dillon had it right when he said in his book "Wrestlers are Like Seagulls" -
"The reason why people like Ric Flair and Hulk Hogan still wrestle is because no one has come along who can do it better than they can."
But hey, I can dream, can't I?