In the first-ever Royal Rumble to have put the WWF Championship on the line, #3 entry Ric Flair outlasted 29 other men to win the vacant title and take his place at the top of yet another promotion.
This title reign earns a spot on this list both for how he won it and for how he lost it. The Rumble that saw him win the title is often regarded as the greatest of all time, as it was stacked to the brim with top-tier talent like Hulk Hogan, The Undertaker, Roddy Piper, and Sid Justice, among others. Flair's post-match promo was equally excellent, as he proudly proclaimed, with a tear in his eye, "this is the greatest moment in my life". And it's hard to fault him for thinking that way, seeing as he'd just reached the pinnacle of what was perhaps the only North American wrestling promotion where he was not a World Champion.
After a 77-day-long reign, Flair lost his championship to "Macho Man" Randy Savage at a terrific yet oft-overlooked match at WrestleMania VIII. Leave it to the Nature Boy for making such a short run at the top so special.