#2 Sting wins his first World Championship (1990)
The 1990 Great American Bash main event between World Champion "Nature Boy" Ric Flair and Sting was a passing of the torch in a lot of ways. Kind of. I mean, Flair would go on to hold a World Championship numerous other times - including twice in what is now the WWE - and be a major figure in the business for decades following this match. He's Ric Flair. Of course he did.
At the same time, however, Flair helped move Sting from "popular guy" to "the guy." The Stinger didn't win in overwhelming fashion, either. Rather than a big dramatic, powerful ending - like a submission or a decisive pinfall, Sting reversed Flair's Figure Four leglock into a small package for the pin. That showed the audience that he had the actual wrestling chops to go toe-to-toe with the best in the business and was deserving of the World Championship.
Sting has had a treasure trove of accolades and achievements since this moment - including a match at WWE WrestleMania that nobody ever though we'd see. But, anyone who looks as Sting's career will, without a doubt, see this moment as the point Sting began his journey from "great pro wrestler" to "legend" and WWE Hall of Famer.