NWA Champion Harley Race thought Ric Flair was such a threat to his title reign that he put a $25,000 bounty on the Nature Boy's head – and "Cowboy" Bob Orton, Jr., and Dick Slater tried to collect with a brutal attack. Flair even announced his retirement due to injuries from the beating.

But "Naitch" wouldn't stay down for long and challenged Race at Starrcade, where he won his second NWA Championship.

Watch Flair upend Race

Flair and Ricky "The Dragon" Steamboat's rivalry dated back to the 1970s, but their war over the NWA Championship in 1989 was legendary. Perhaps no two foes were as evenly matched in in-ring technique and style as Flair and Steamboat.

Some experts believed that Steamboat had gotten the better of Flair when he defeated him for the NWA Title and had repeatedly turned back his challenges in closely-fought, but controversial, rematches. In many ways, Flair's back was up against the wall in this encounter with The Dragon.  

Watch Flair slay The Dragon

In the 1980s, Hulk Hogan was the face of WWE while Flair embodied the NWA, WWE's chief rival. So, the Nature Boy's arrival in WWE in 1991 was an event that so-called experts thought they'd never see.

Flair didn't waste any time sparking controversy. With Bobby "The Brain" Heenan at his side, he brought the NWA Championship with him and referred to himself as the "Real World Champion," a direct slap in the face to The Hulkster. It wasn't long before Hogan and Flair squared off in the squared circle.

Watch Flair's 1991 WWE Debut

Watch Flair challenge Hogan

After Flair played a pivotal role in the controversial ending to the WWE Championship Match between Hogan and Undertaker at Tuesday in Texas, WWE President Jack Tunney held up the WWE Championship. This set the stage for the most high-stakes Royal Rumble ever in 1992 as Ric Flair proved he was the "Real World Champion" by outlasting 29 other men to win the title.

Flair has always said, "To be the man, you've got to beat the man." On this night, he showed the world he was truly "the man."

Watch Flair win Royal Rumble

Almost no one gave Flair a fighting chance when he challenged the 450-pound Vader for the WCW Championship at Starrcade in 1993.

Immensely powerful and sadistic, Vader outweighed Flair by more than 200 pounds and had an unpredecented agility for a man his size. He had dominated Japan and won championships on several different continents. It was no wonder that Vader was recognized as the best big man in the game at the time.

Still, Flair believed he was the best man in the game, period, and showed the Colorado native how dirty he could be at Starrcade.

Watch Flair humble Vader

The Chairman thought he could bask in one of his greatest victories when his pro-WWE team defeated the Shane and Stephanie McMahon-led Alliance at Survivor Series in 2001. Mr. McMahon had not only put WCW out of business, but had thwarted the takeover attempt by his children.

However, when Flair emerged and revealed that he had helped bankroll Shane's purchase of WCW and was a part owner of WWE, McMahon was livid. Tension boiled over into a Street Fight at the 2002 Royal Rumble.

Watch Flair take on the Chairman

Story: The Real Story Behind McMahon's Ultimatum

Flair has conceded he didn't truly feel like he was himself in the ring after his return to WWE – until he faced Undertaker at WrestleMania X8.

The Phenom's attack on Flair's son, David, not only goaded him into the match, but ignited a fire that had been dormant in the Nature Boy. Although he ultimately lost, Flair pushed Undertaker to the limit and showed the world that he was truly back.

Watch Flair vs. The Phenom

Brett Favre may be an ageless wonder in Green Bay, but he has nothing on "Naitch." In 2005, more than 30 years after his debut, followed by 16 World Championships, Flair achieved a first in his career: He won the Intercontinental Championship.

The younger, cocky Carlito – whose father, Carlos Colon, had battled Flair for the NWA Championship years ago – thought he would have a cakewalk with the Nature Boy. But Flair took the Caribbean Bad Apple to school and made him cry uncle to his patented Figure Four Leglock. Intercontinental Champion Ric Flair – now that's cool. Whooo!!!

Watch Flair win the Intercontinental Title

Watch Flair's victory celebration

They have had a mentor-student relationship. They have been teammates in Evolution. Triple H grew up idolizing Ric Flair; the Nature Boy regards The Game as the greatest in the game today. Now, under Mr. McMahon's win or retire ultimatum, these two mirror images are forced to go to war against each other, and Flair must fight for his professional life against one of his best friends.

Can Flair be the Dirtiest Player in the game against Triple H? And can The Game bring his best against his idol?

Watch the Chairman issue Flair an ultimatum

Watch Flair's do-or-die victory over Randy Orton

Watch the Nature Boy survive Umaga

Story: Triple H and Flair's Dilemma