Hello, everybody, and welcome to another episode of Wrestling Tales, Stories from the Ring and Beyond.

I'm Sean Mooney.

And today, we are diving into something that is still strangely fascinating when you look back at it.

Vince McMahon outside the wrestling bubble. Now think about this for a second.

Now, this is a man who on WWE television has played a tyrannical billionaire, started cult-like factions,

feuded with his own family, been blown up in a limousine, remember that, and basically portrayed the

most over-the-top evil boss in entertainment history. But outside of wrestling, it was a very

different world for him. One, he has never been able to be very comfortable in. To this day,

there are very few on the planet who can say they truly know the real

Vince McMahon, a man who, outside of wrestling, has also been incredibly private. And honestly,

that's what makes these old late-night talk show appearances so interesting, because it was a time

when you got to see what happened with the most

powerful man in wrestling stepped outside of the WWE's controlled environment and into the real

world. Today, we're looking at two very different appearances. One from 1989 with David Letterman. Remember him? And another from 1999 with

Conan O'Brien. Same guy, same business, but two completely eras of wrestling and two completely

different versions of Vince McMahon, or Mr. McMahon, as he would become known.

Now, the thing about Vince McMahon is that he never really operated on the same wavelength as everybody else.

I can attest to that.

Some people call him a genius.

Others call him insane. And honestly, there's probably

truth in both. This is a guy who revolutionized wrestling, transformed the WWE into a global empire,

and completely changed sports entertainment forever. That is absolutely true. But he also had moments where he seemed almost

...