5. Ric Flair Vs. Shawn Michaels (WrestleMania 24)
Ric Flair is among the most influential wrestlers in history. While his most memorable moments and matches took place outside of WWE, he still had a notable tenure with the company across two runs, from 1991 to 1993, and again from 2001 to 2008. Despite being well past his prime, the Nature Boy still managed to deliver some quality matches during his time in the company.
In late 2007, after Flair stated that he would never retire, Vince McMahon announced that the next time Flair lost a match, it would be his last. Over the following months, Flair won match after match, keeping his career alive with each victory. Eventually, he challenged Shawn Michaels to a match at WrestleMania 24.
The two wrestlers fought a deeply emotional match, as Flair tried his best to keep his career alive. However, he came up short, as Michaels won the match after delivering a Sweet Chin Music after uttering the words, “I’m sorry, I love you”, which would become one of the most iconic wrestling moments ever.
While this still remains Flair’s last WWE match, he tarnished the legacy of this farewell by continuing to wrestle in other promotions, wrestling as recently as 2022. Knowing Flair, he could very well come out of retirement again, but still, this WrestleMania farewell remains absolutely iconic.
