The late 1990s were a weird time for WCW. They saw a big rise in popularity, fans, and earnings followed by a lack of action and some ridiculous writing. Obviously, we blame this on the fact that there just wasn’t enough of the Nature Boy in the mix. Ric Flair was out of the game for a while due to contract disputes. We did get at least one pretty awesome promo out of it though…
Flair participated in a few storylines at WCW during those years, however weird they were. For instance, he became “President of WCW” for life and then got committed to a mental hospital after going crazy with power. (Yeah, we aren’t sure why either.) So we’re gonna fast-forward to the 2000s when we got some real action and emotion from ol’ Naitch.
Ric Flair vs. Triple H at Taboo Tuesday, 2005
At the ripe age of 56, Flair was still kickin’. Triple H is a self-proclaimed admirer of Ric Flair (aren’t we all?) and they had a few matches during 2005. This one was arguably the best though, as the two showed great chemistry and tons of endurance. Sure, it’s not the late 80s, early 90s Nature Boy, but the man’s still got it! It was very much a case of the student taking on the master, with Triple H offering to put Flair out of his misery so he could “stop embarrassing himself.” It fit their relationship well and was superb storytelling.
As expected, Triple H controlled the whole match, beating on a resilient old Flair. The crowd was loud and crazy, and the fact that it was a bloody, brutal cage match didn’t hurt either. Flair targeted H’s “hurt knee” and we got a look at the wrestler that Nature Boy used to be. We saw him lock on the Figure Four and give Triple H the middle finger, nail him with a chair, and escape the cage to win the match. WOOO!
Flair vs. Edge on Raw, 2006
A small bout in the grand scheme of things, this tables, ladder, and chairs match showed just how much Flair could still do. The aim of the match was to climb the ladder and grab the suspended WWE Championship belt, and the commentators made a big to-do over how Flair had no experience with these sorts of violent matches. Edge, the WWE Champion, was just starting to explode on the scene and with Flair’s help, he would go even further.
This match ended up being so brutal that the crowd started chanting “Holy shit” after Flair got slammed through a table. (Charlotte Flair even makes an appearance, yelling “Dad, get up!” from her seat.) And as he always does, however, The Nature Boy returned with a vengeance, learning quickly how to use a chair and ladder to his advantage, popping Edge with several good ones and, again, targeting his opponent’s weak spot – his knee. A bloody Flair climbed the ladder and nearly won the match before being punched repeatedly in the face and eventually knocked off, allowing Edge to grab the belt retain the title.
Flair vs. The Undertaker, WrestleMania X8, 2002
The Undertaker was big time in the early 2000s. Scary, dark, and terrifying people with the chokeslam, he rode out on his motorcycle for a shot at Ric Flair during Wrestlemania in a “no disqualification” match.
Flair sparked the feud by insinuating himself into one of the Undertaker’s matches and bashing him on the head with a pipe. The Nature Boy said no to a match with the Undertaker, so The Undertaker forced his hand by attacking Flair’s best friend and later his son David, leaving them bloody and beaten. He told Flair the attacks were on his head, and finally Flair accepted a match with the Undertaker at Wrestlemania (despite the better judgment of the “WWE Board.”)
Flair took a beating, kept the crowd in it, and made quite a few comebacks throughout the match, getting close to beating the Undertaker with a Figure Four and throwing a few chairs in the process. The Undertaker won, but it showed Flair could still run a PPV-caliber match.
Flair’s Last Match vs. Shawn Michaels at Wrestlemania 24
This one is sentimental. Okay, it’s downright emotional. Flair and Shawn Michaels put on a hell of a show to end The Nature Boy’s career. Named as the 2008 Match of the Year by Pro Wrestling Illustrated, the story was layered and the tears were real. Flair had to pick someone who was great so he could show he was still a legend that could fight with the best of them. And Shawn Michaels had to come to terms with possibly ending the career of one of his heroes. Could he actually do it? This match was a real tribute to Ric Flair.
Michaels mouths “I’m sorry” before kicking Flair and pinning him to win the match. More story and emotion than true action, it’s a fan favorite for a reason. It’s the symbolic end of Flair’s wrestling career. Even though we were destined to hear more from him, post-match Flair holding his hands up to the crowd in thanks and basking in their cheers is still tear-jerking.
That might be the end of this list, but oh boy, we’ve still got a lot more favorite Ric Flair moments. The man just can’t stay away from professional wrestling!