#3 The WWE's top title has been contested for twice in the Royal Rumble Match
In the late summer and fall of 1991, Bobby "The Brain" Heenan proclaimed the coming of "The Real World's Champion" to the WWF, carrying around NWA/WCW's World Heavyweight Championship (which, in real life, Ric Flair was held hostage until a disputed $25,000 deposit was returned); Flair eventually made his way north to the WWF, and instantly became an agent of chaos, costing Hulk Hogan his WWF Championship against The Undertaker at Survivor Series, then interfering again in the championship rematch at This Tuesday in Texas.
WWF [kayfabe] President Jack Tunney vacated the belt due to the illegitimacy of the two title matches, and announced that a new champion would be crowned in the 1992 Royal Rumble Match; in what many consider both the best Rumble match ever and the best commentary performance of Heenan's career, Flair entered at number three and outlasted the field, last eliminating Sid Justice with assistance from an already-eliminated Hogan to claim his first WWF/E title.
Roman Reigns entered 2016 the defending WWE World Heavyweight Champion, having defeated Sheamus on Monday Night RAW to reclaim the belt (which Sheamus himself beat Reigns for at Survivor Series just over five minutes after Reigns won a tournament for the vacated title). Looking to rekindle some of the "Stone Cold" Steve Austin magic, WWE Chairman Vince McMahon joined his daughter Stephanie and son-in-law Triple H in opposing The Big Dog's rise.
As retaliation for Reigns attacking the Chairman during that RAW title change, McMahon announced that Reigns would have to defend the title against 29 other men in the 2016 Royal Rumble match; the match, which saw the WWE debut of AJ Styles, also saw The Game become a surprise entrant at number 30. Unfortunately, Helmsley received more cheers than boos for eliminating the future yard owner, before electrifying the crowd in a back-and-forth battle with Dean Ambrose. Helmsley backdropped The Lunatic Fringe over the top, claiming his 14th world title reign with a Royal Rumble win.