10. Vs. Ric Flair - Prime Time Wrestling 1991 https://www.youtube.com/watch?v=_L-LAp8PoZQ Shawn's participation in the 'final' match of Ric Flair's career in 2008 is much more renowned and celebrated; but this encounter that took place a whole 17 years earlier gave us the first glimpse of the in-ring chemistry between the Heartbreak Kid and the Nature Boy. In 1991 the careers of both men were in much different places - Flair was a solidified main eventer (he won the WWE title not long after this match), and Shawn was essentially a rookie, and still a tag team wrestler, as a part of The Rockers with Marty Jannetty. He had, however, began to show the signs of his athletic and storytelling abilities that he'd improve upon in later years. Going up against a main eventer, this should have been a glorified squash match, but instead it was a much more back-and-forth contest. Shawn was given time to go on the offense, and time to demonstrate his move-set, charisma and personality. Flair, as the main event guy, could have dominated the match entirely, but was generous with Shawn and as a result there was a genuine intensity to the match, and although it was pretty clear Shawn was never going to win, the match had much more of a competitive edge than expected.