Well, he won 1990 and 1991. 1990 was just a fantastic PPV. The crowd was incredibly hot all night, the matches throughout were solid, and the Royal Rumble match is probably the best of all. From DiBiase staying in for what seemed like an eternity (back before such thing was common) at the number 1 spot, to the incredible eruption that Warrior got, to the bigger reaction Hogan got, to the even bigger reaction when Warrior finally eliminated DiBiase, and to the moment it nearly blew the roof off when Warrior and Hogan finally matched up one-on-one with each other.
There was a fantastic story told in this RR match, more so than I think I've seen in any other match, and it set the main-event of Wrestlemania up beautifully.
1990 is the best.