15 EXACT Moments Failed WWE Attitude Era Gimmicks Actually Got Over

8. Shane McMahon (January 18, 1999)

Shane McMahon was originally introduced as a WWF regular in August 1998 by his dad Vince on the premiere of Sunday Night Heat. He was there to do commentary like Vince before him. It was a weird period. Shane was cocky and was flanked by two babes, but he wasn’t an overt heel. It was hard to tell whether you were meant to like him as a hip young guy, or what. He was insufferable, so it didn’t work, but this was just an experiment designed to loosen him up and make fans aware of him ahead of his run.

Shane evolved into a proper character when he turned babyface, by aligning with Steve Austin - but only to set up a swerve-turn at Survivor Series 1998. Shane refused to count Austin’s pin over Mankind, stopping at two and flipping Austin the bird. This drew a monstrous reaction, but anybody could have screwed Steve Austin and drawn boos, even Tiger Ali Singh. Shane’s dramatic timing was strong, his cowardly sprint away from the scene even better, but for a few weeks, he was just a smirking background player with one default setting: smug. The first time fans “got” Shane and his distinct brand of charisma was when he trained his dad for the 1999 Royal Rumble match. Shane became a hyperactive brat so arrogant that he thought his powers of motivation and hype-man act alone could build Mr. McMahon into a WrestleMania headliner. 

Shane was absolutely full of sh*t, of course, but his extravagant level of confidence was a winning act. “Catch the chicken! Get that chicken! Get the chicken!”

So in love with the sound of his own voice that he never shut the hell up, even once, this incredible skit is where it all clicked.