12 Definitive WWE Attitude Era Matches

9. "Stone Cold" Steve Austin vs. Vince McMahon - St. Valentine's Day Massacre

The rivalry between "Stone Cold" Steve Austin and Vince McMahon was the biggest, and most important, of the Attitude Era. It fueled viewership, drew huge ratings and led the company past WCW in the Monday Night Wars. But they never had an actual wrestling match. Sure, their "match" in April 1998 resulted in the first win for Raw over Nitro in over two years, but that never really got started, thanks to the interference of Dude Love. As 1999 arrived, the industry icons prepared for battle, Austin's chance of headlining WrestleMania on the line in a Steel Cage match. With members of The Corporation unable to come to his aid, McMahon would have to face the one man whose life he had made a living hell over the last year. Austin beat the unholy hell out of McMahon, battering him from one side of the cage to the other. He even sent the Chairman of the Board crashing from the top of the cage through an announce table at ringside, breaking his boss' tailbone in the process. The debut of Paul "Big Show" Wight accentuated what was already a monumental match in Attitude Era lore while his tossing of Austin into the cage, breaking the structure and allowing Stone Cold to score the win. McMahon had been vanquished and Austin was on his way to the first of three WrestleMania showdowns with The Rock. More on that rivalry in a bit.