History Of WWE's Attitude Era In 10 Matches
6. Vince McMahon Vs. Steve Austin (St. Valentine's Day Massacre 1999)
Key to Austin's success was the character of Mr. McMahon. There was no more powerful enemy for the anti-hero babyface Stone Cold to have than the actual boss of the company he represented as WWF Champion. Austin and McMahon were at odds throughout 1998, producing segments so hot and well-received they almost seemed to be guided by witchcraft.
People couldn't get enough of seeing the rebellious employee kick the tar out of his smug, stuffy boss. Come 1999, it was time for McMahon and Austin to settle their problems inside a Steel Cage. That match took place in February at the St. Valentine's Day Massacre show.
The Big Show (referred to that night on commentary as 'Paul Wight') would make his debut on the pay-per-view, literally hurling Austin through the cage side and accidentally allowing him to secure the victory. It was quite the ending, one that allowed the rivalry to continue.
There's perhaps no better match with which to sum up what the 'Attitude Era' was like than McMahon vs. Austin. Largely a commentator on screen up until his feud with Austin really took off, Vince was the yin to Austin's yang.