1. I'm kind of split between the I Quit match with Terry Funk and Starrcade '93 with Vader. I didn't see the I Quit match until over 10 years after it happened and even in '89, seemed to be a match that would have been just as good had it taken place recently. Starrcade '93, however, I saw shortly after it was released on VHS and just the backstory of Flair's career being on the line and his performance make that match one of my favorites. The 2 matches I'll point to is someone says Flair worked the same match every night.
2. Ricky Steamboat. These guys pretty much faced off over the course of 3 decades, which provides the ability to be perfectly comfortable working with one another. Not to mention, their 3 matches from 1989 received 5 star ratings and I also feel their final match with one another in 1994 on WCW Saturday Night should be up there as well.
3. My favorite memory is the night Arn Anderson introduced the Horsemen, with Dean Malenko as the newest member and says he almost forgot the 4th Horsemen, Ric Flair. And Flair comes out and cuts that "abuse of power" promo on Bischoff. Oh man, I remember my heart beating so fast as a kid when Flair came out and you could see the emotion, as Flair was near tears that night.
4. I loved his promos. They fit him perfectly. A loud, obnoxious guy that touted himself as the best and could back it up. A lot of wrestlers promos today aren't as overly cocky as Flair's was. He bragged about every facet of his life, which was actually true. He acted as a champion and lived his life as a champion and made no hesitation to let fans know anytime he was on the microphone.
As for in ring ability, many say Flair wrestles the same match every night. Not hardly. Everybody has their signature moves but not every wrestler tells a story in that ring. Flair made his matches mean something and I'd say all the way up until 1996, Flair would work nearly every match as if it was a PPV main event. He was a master in the ring that could manipulate the referee, allowing him to do something heinous, earning him the title of "dirtiest player in the game". The fact that he could constantly go out there in the late 80s and wrestle in excess of 30 minutes night in and night out means a lot. And he was able to do that with everybody, from seasoned veterans like Steamboat & Funk to a borderline newcomer Sting to a green as green can get Luger to 450 pound powerhouse like Vader and everybody in between. Bret Hart is probably the only other guy that could maintain quality matches with such a variety of talent, with various size and skill levels.
5. I'd put him in my top 10, maybe even around 5 or 6. No matter the reason he stayed on top or any of the backstage shit, that guy was one of the best workers this business will ever see. Flair was the reason WCW lasted as long as it did, as he carried that company for 3 years, not counting his hardwork in JCP in the 7 years prior to them selling. He was WCW's answer to Hogan and a guy that defined what a champion should be.