Re: Which Royal Rumbles do you consider the most entertaining?
Well lets see....
I really liked 1990. I know that was before the Royal Rumble meant anything in the grand scheme of things, which is probably why it gets over looked. But it has so many great stars & big names that it feels huge. Savage, DiBiase, Roberts, Andre, Piper, Rhodes, Perfect, Rude, and of course Hogan & Warrior. That later two in fact gave me my favorite Rumble moment ever. To watch Hulk Hogan & The Ultimate Warrior clash one on one for the first time was HUGE. It was one of those "time has stood still" type of wrestling moments. They didn't even do that much either, obviously to keep wetting our appetites for Wrestlemania VI. Also, I give a ton of credit to Ted DiBiase for his performance in this match as it was, to me, the first truly great "Marathon Man" Rumble performance.
1991 is a bit of an underrated one I feel. Yes, Hogan just won again, and yes, this was before the outcome actually mattered (though Hogan did end up getting the Wrestlemania title shot after this). What makes this one stand out to me though is the number of marathon men this one had. Rick Martel set the then record of over 52 minutes and Valentine lasted close to 45, with Tito Santana & Hercules lasting over 30 and several others like Earthquake, Bret Hart, Texas Tornado, & Shane Douglas lasting over 20. It was the first time we got to see a lot of guys last a really long time to really sell the idea of having to last a long time to win the thing. Heck, Hogan entered at 24 and won the thing, and in there just under 20 minutes despite the late entry.
1992 was also a huge one. It had a great array of star power and also greatly raised stakes by having the winner crowned the new WWF Champion. This was the first Royal Rumble that wasn't just an attraction to sell a PPV. The outcome actually mattered and it was going to be a huge deal. Obviously Flair gave one of the greatest performances of his career as he went in at Number 3 and lasted all the way to the end to win it, giving us great drama along the way.
1994 is another favorite of mine. It was the Diesel run year where Diesel dominated the early going of the match and eliminated as many as seven guys and even went on a stretch where he was the last one left and eliminating new entries one at a time. It was one of the earliest examples of a giant taking full control of the Rumble. This Rumble also has another one of my favorite Rumble moments. Bret Hart had been injured earlier in the night by The Quebeckers and later his jealous brother Owen during a Tag Team Title match. Bret's role in the Rumble match was in question as he left the arena on a stretcher. One number goes off, and nobody comes out. Everyone assumes it is Bret Hart. But then, two numbers later, BRET HART limps towards the ring to a thunderous ovation. It was a perfectly executed emotional moment. And then of course there was that fantastic ending where Lex Luger & Bret Hart flipped over and hit the floor at the same time. After a lot of deliberation and keeping us on the edge of our seats, they finally announce both men as Co Winners of the Royal Rumble. It is the type of ending you really can't do twice, and it certainly helps set this Rumble match apart from the rest.
1998 also stands out to me. That was the year where it was Steve Austin Vs. The World where he basically had every heel gunning for him because, well, he's Steve Austin and he's a dick and he had pissed everyone off at some point. We also got another truly memorable Royal Rumble moment. Not only did the match start off with Cactus Jack taking on his partner Chainsaw Charlie (Terry Funk) in a duel of the chairs, but Mick Foley would shock us by entering the Royal Rumble as all three of his different personalities. We got Cactus Jack, Mankind, & Dude Love all at different portions of the match. It was really a sight to see unfold. And I shouldn't even have to say that Austin's victory was the start of something special.
2001 was also a highly entertaining one. We got a Hardcore Battle Royal, a clash between the Hardy Boys, an Undertaker/Kane reunion, some entertaining returns (like Big Show chokeslamming the hell out of everyone), some great star power like Steve Austin & The Rock, oh, and we got a Drew Carey cameo that was actually kind of funny. The major thing that really sticks out to me about this Rumble is that Kane gave what I would argue is one of the greatest booked Rumble appearances ever. Kane as a monster lends himself to dominant performances, but his early entry at 5 allowed for him to dominate the whole match, giving him a hybrid run of being both the monster & the marathon man. It was very cool and by the end of it, I was actually kind of sad that Kane didn't win the match, ha ha.
2004 was another enjoyable one filled with all the great stuff we come to expect out of a Royal Rumble...and unfortunately it is the one we aren't supposed to remember because of He-Who-Must-Not-Be-Named.
2007 was an outstanding one as well, mainly for its ending. Undertaker, Shawn Michaels, Edge, & Randy Orton might be the best final four in the history of the Rumble. And the ending between Shawn Michaels & The Undertaker might be a MOTY candidate in of itself. It was just great work between two great stars. This match also had probably the best use of The Great Khali ever as he just tore shit up in there and threw people around like ragdolls.