The foundation of WWE's Attitude Era was built around the revolutionary rivalry between the rebel, Stone Cold Steve Austin and the boss, Vince McMahon. Austin, who refused to bow down to authority clashed with the antagonizing Mr. McMahon on a weekly basis, creating some of the most entertaining television in WWE history.
As the 1999 Royal Rumble approached, we were right in the middle of the Austin versus McMahon war. Naturally, both men were scheduled to enter the Royal Rumble match as the first two entrants. A wrinkle was added to the fold as McMahon put a $100,000 bounty on Austin's head claiming that the superstar who eliminated Austin from the Royal Rumble match would receive the payment. He was willing to do anything and everything to make sure Austin did not win the Royal Rumble.
A satisfying beatdown of the boss early on in the match eventually led to McMahon escaping through the crowd and leading Austin into a trap. As they ran through the arena, Austin was ambushed by McMahon's corporate henchmen. They pummeled him, sending him on a storyline trip to the hospital.
The arrogant, yet always amusing, Mr. McMahon character proudly joined the commentary team to observe the rest of the Royal Rumble match with a smile on his face. The smile was short-lived, however, when an ambulance was shown arriving to the arena. Stone Cold Steve Austin was the driver.
Much to McMahon's dismay, Austin rejoined the match, tossing out a number of individuals until it was down to the two men who started it. Austin continued his annihilation of McMahon until the boss' comrade and WWE champion The Rock made his presence felt by distracting Austin, leading to the unlikeliest of all Royal Rumble victories. In a shocking turn of events, Vince McMahon eliminated Stone Cold Steve Austin to win the 1999 Royal Rumble, earning a WWE Championship opportunity at WrestleMania 15.
Despite the victory, McMahon had no intentions of challenging for the WWE Championship at WrestleMania with The Rock as the champion. Instead, the No. 1 contender spot was put on the line in a memorable steel cage match a month later at the St. Valentine's Day Massacre event.
When it was all said and done, Austin did make the main event at WrestleMania that year and took the WWE Championship from The Rock, but the road traveled was unforgettable.