Event: Royal Rumble 1996
Date: January 21, 1996
Location: Selland Arena in Fresno, California
Winner: Shawn Michaels
Last Eliminated: Diesel
Iron Man: Triple H
Quickest Out: Squat Team #2
Most Eliminations: Shawn Michaels
This match was historic because it was the first Rumble match to feature the entrance music being played for each wrestler as they came in. In hindsight, it's crazy that they ever didn't do that, but this is the one that started the trend that hasn't changed since. And never will.
This also marked the second time a wrestler won the Rumble in consecutive years with Shawn Michaels accomplishing the feat from the number 18 spot. His win ultimately led to his victory over Bret Hart at WrestleMania 12 in one of the most beloved Iron Man matches of all time.
Triple H started his rise at this show. He lost via disqualification in a match on the "Free For All" pre-show before the event, which gave him the number one slot. He lasted 48:01 of the 58:49, becoming Iron Man for the match and beginning him on his path to the top.
Unfortunately, a few months later he was jobbing to Ultimate Warrior at WrestleMania and then becoming a major casualty to the Curtain Call at Madison Square Garden in May of that year.
This certainly wasn't a bad Rumble match but it was still in the dark ages for the WWF and this was a period where Michaels was doing what he wanted and Vince McMahon was letting it happen because he was basically in love with the guy. In hindsight, The Kliq dominated this show, with Triple H going Iron Man, Diesel (Kevin Nash) lasting to the final two and having a moment with Michaels to end the show, and, of course, Michaels winning.
Be on the lookout for Isaac Yankem, one of the best characters ever: