6. Mike Tyson Becomes Steve Austin's Roadblock (1998)
The media frenzy was just what the WWF needed. On January 19, 1998, one night after winning the Royal Rumble, Austin got in the face of Tyson, who made a guest Raw appearance to ostensibly announce his participation in WrestleMania XIV. Austin took exception to Tyson being declared, "The Baddest Man on the Planet", and facilitated a brawl with Tyson and his posse that made plenty of news shows, including SportsCenter. Weeks later, with Tyson now named the 'special enforcer' for Austin's title match with champion Shawn Michaels, Tyson aligned himself with Michaels' D-Generation X group, one of the earlier instances of a babyface needing to overcome authoritative odds in a World title match. Austin was further embarrassed by the two during the public workout days before WrestleMania, when he was tied in the ropes and had his head mockingly kissed by Michaels and Tyson simultaneously. The story was more about Austin breaking through to claim his first World title, but the celebrity intrigue provided by Tyson put the outcome a hair further into doubt.