7. Vs Shawn Michaels
This is another match that just makes sense on obvious levels. These two are friends in real life, sharing in their strong faith and beliefs. They're also the pictures of loyalty from the Monday Night War. With nearly every other big name "jumping ship" at least once during the Attitude Era, Sting was 100% behind WCW, and Shawn Michaels was 100% behind the WWF. Even someone like The Undertaker, who has now been working for Vince McMahon for nearly 24 years, had some time with WCW, albeit before the Monday Night War began. If you recall, Michaels had yet to return to the business when WCW folded. When WCW was purchased, Michaels was still nearly a year-and-a-half away from his comeback. If Sting arrived with the rest of his WCW brethren, he would have had to wait a couple years before this match could have taken place. If you look at Shawn Michaels' WrestleMania matches from that era, you have a match with Chris Jericho at Mania 19, the triple threat with Triple H and Chris Benoit at 20, Kurt Angle at 21, Vince McMahon at 22, John Cena at 23, Ric Flair at 24, and The Undertaker at 25 and 26. That doesn't really leave a lot of room for a Michaels VS Sting WrestleMania blockbuster. Perhaps you could replace Vince with Sting at 22, but every other match HBK had in that stretch made perfect sense from a booking and storyline perspective. Whenever the match took place, it would have received tremendous hype behind it, and for good reason. Those two helped to define their respective promotions for an entire generation.