There’s a great line from a Raw in 1998: Vince McMahon had just stolen Steve Austin’s championship belt and says “the only place this belt belongs is above my mantle in one of my homes.” That single hilariously brilliant line perfectly encapsulated the evil rich bastard character that was heel Vince McMahon. And yet in early 1999 the unthinkable was happening and Vince McMahon was transitioning from heel (bad guy) to face (good guy).

Now I will admit this turn was expertly done. It was impossible for anyone to empathize with McMahon himself (a spoiled rich asshole who had victimized ever face in the WWF), so instead he garnered sympathy by proxy by having his innocent daughter Stephanie get attacked by the Undertaker. This led to him seeking help from Steve Austin and while the crowd still hated him his contrition and humility made him at least somewhat understandable if not likable. Next, his son Shane started attacking him and victimizing face wrestlers, overtly taking the spot that Vince had once occupied as the spoiled rich asshole of the WWF. This implicitly moved Vince away from being a heel as he was no longer doing the victimizing and was in fact being victimized himself. Finally, after Undertaker and Shane announced they had been working together the whole time, Vince came out and attacked Shane for the benefit of Steve Austin during a match Austin had with the Undertaker. By siding with the WWF’s biggest face, and attacking its two biggest heels, Vince had now fully turned from heel to face.

And yet… it was kind of crap. Making Undertaker be a “Greater Evil” over an above Vince was definitely cool, but trying to make Vince sympathetic on his own merits was just kind of boring. There was a novelty to having two sworn enemies (Austin and McMahon) have to work together, but the novelty wore off quickly when Vince came out and tried to cut a face promo saying how he knew he had been an asshole and would try to change as a human being. And you could tell the crowd wasn’t having it, they continued to chant “asshole” at him no matter what he said. Now, knowing as I do the future of the WWF, I know exactly where this storyline is going: Vince eventually reveals that he was secretly behind everything and was working with Undertaker the whole time as a heel. But I have to wonder why they ever tried to portray him as a face in the first place. Was it all for the unexpected twist that he was working with the Undertaker? Shocking though it was, it was also really really stupid to have him sobbing about the victimization of his daughter only to a few weeks later be revealed as the architect of that same victimization. Had they actually wanted him to be a face? I can’t imagine anyone thought that was a good idea, the crowd still hated him for everything he had done and a spoiled rich company owner just doesn’t make for a natural “good guy” character in any way shape or form. Maybe Vince personally wanted to be portrayed as a good guy just for his ego, but then someone should have told him it just wasn’t going to happen.

Despite a few moments of humor during Vince’s aborted face run, like giving a terrible Stone Cold Stunner to his son Shane, the whole thing kind of felt boring and subpar as I was watching it. I would have preferred Vince to have still explicitly been a bad guy throughout, just a bad guy who loved his own daughter. Then he could have had humorous promos demeaning the crowd and complaining about his situation, instead of boring promos where he tried to act sympathetic while complaining about his situation. But regardless, face Vince McMahon doesn’t detract from the stellar performance that Raw has done after Wrestlemania 1999.