3 of Vince McMahon's worst character ideas and 2 of his best

Vince McMahon is the most important name in the history of pro wrestling. There have been many major stars throughout the decades of the business, but ultimately, the most dominant man behind-the-scenes for the last 3+ decades has been none other than Vincent Kennedy McMahon himself.

McMahon not only took the WWF to new heights, but he destroyed the territory system single-handedly while doing so. Many don't realize just how hard he works. It's hard to find anyone who works harder than he does, because he's known to be a personality who micromanages and has his fingers dipped in every slice of the pie, so to speak.

One of these aspects is the creative department. Ultimately, Vince McMahon has the final say on everything and many of the gimmicks and characters we've seen over the years were his brainchild. Naturally, some were major flops, some were hit or miss and some were absolute moneymakers. We look at both the best and worst of his character creations!

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#3. Worst - Fake Diesel and fake Razor Ramon

This was a disaster, to say the least

Diesel and Razor Ramon were two extremely essential superstars to WWF's Golden Generation era. Diesel in particular was being built to be the next face of the company, but things just didn't pan out and the company found itself dipping into record-low ratings.

WCW was on the rise at the time and managed to woo Kevin Nash and Scott Hall, who appeared as "The Outsiders". With two major stars gone, Vince McMahon seemed to think that they were easily replaceable and that they're just characters.

Unfortunately, he was dead wrong. Glenn Jacobs, AKA Kane played the role of the fake Diesel and it was an instant flop. It's no surprise that WWF was quick to pull them and repackage them. It certainly worked out for Glenn Jacobs anyway.

"The Outsiders", entering the WCW can be regarded as the moment that triggered "The Monday Night Wars." The next few years witnessed some of the top talent changing brands to find greener pastures in enemy territory.

The WWE ultimately won the duel with WCW and Nash and Hall returned back to Vince McMahon's territory under their NWO guise.

#2. Worst - Dr. Isaac Yankem

The story behind this is hilarious

Back to Glenn Jacobs, it's a real miracle that he managed to become a legend of that caliber. But that's a power of a good gimmick. The power of a bad gimmick, unfortunately, isn't very flattering and Jacobs learned it the hard way when he was Dr. Isaac Yankem, an evil dentist.

Kane even recalled the absolutely hilarious story behind how Vince McMahon pitched Isaac Yankem to him. In an appearance on The Steve Austin Show Podcast, Glenn Jacobs recalled the meeting.

“Everything is going well [in a meeting] and then Vince asks me, ‘Glenn, have you ever been afraid to go to the dentist?’ and I think this is one of those things where I’m going to a personality test or something. I’m like, ‘No, sir’ and he’s like, ‘You know, I’ve always had this idea for a wrestling dentist: Isaac Yankem… I yank ’em!’ and then he starts doing the Vince laugh, right? I’m looking at this one individual in this business to break into the big leagues and I’m sitting there with a blank face trying not to react. He says, ‘I think you’ll be great for it’ and then he walks out! I’m sitting there and I went from on top of the world to feeling the world has fallen on top of me. Because I’m like, a wrestling dentist?! How am I gonna pull this off?!”

One can only imagine his reaction to that pitch.

The gimmick lasted for less than two years without making much of an impression with the stakeholders. It was when Jacobs donned the role of Kane, the Undertaker's half brother, that his career took off. The big red machine is one of WWE's greatest gimmicks that struck a chord with the WWE universe.

Jacobs, on a personal level, achieved the status of both a Triple Crown champion and Grand Slam champion with the Kane gimmick. Something a dentist might have found hard to do.

#2. Best - Mr. McMahon

Mr. McMahon would be a defining character in the Attitude Era

It's crazy to think that one of Vince McMahon's greatest character creations is none but himself. The Mr. McMahon character was extremely important for the time and was one of the major catalysts and parts of the Attitude Era.

It all started with the Montreal Screwjob, an incident which essentially outed Vince McMahon as the owner of the company (he had previously taken multiple on-screen roles). After Bret Hart left for WCW, McMahon decided to exploit the situation and turn himself into the biggest heel in the business.

And that's exactly what happened. The evil Mr. McMahon's character would be a defining part of the Attitude Era and perhaps the biggest character responsible for the rise of "Stone Cold" Steve Austin. Their rivalry was absolute money and it showed in the ratings, attendance, reactions and even merchandise sales.

The best part about the character was that the sole objective was to put over other superstars. And that's exactly what happened.

#1. Worst - Rocky Maivia

The Rock had a rough road before stardom

Here's the truth of the matter - Dwayne Johnson was always going to receive a top push. However, Vince McMahon decided at the time to take a more organic approach and that worked wonders, making Johnson one of the biggest stars in the industry's history.

However, before that, Vince McMahon decided to give Johnson the gimmick of Rocky Maivia, in tribute to his grandfather the late, great High Chief Peter Maivia. The only problem was this - the gimmick was terrible.

Rocky came across as the most generic babyface in the world and had absolutely zero depth to him, with the WWE Universe quickly turning on him with chants like "Die Rocky Die". McMahon decided to go the organic route and when he returned from injury, told Johnson that he would turn heel so that he could get over organically.

And thus, 'The most electrifying man in sports entertainment', 'The Rock' was born. The rest, as they say, is history.

It would certainly be interesting to imagine the outcome of the Rocky Maivia gimmick if the fans had taken a liking to it.

#1. Best - The Undertaker

The Undertaker is a timeless legend

On more than one occasion, Vince McMahon has referred to The Undertaker as his "greatest creation." Indeed, he's right about that, because there's no gimmick that he was behind that succeeded more than The Undertaker did.

Little did McMahon himself realize that The Phenom would become one of the pillars of the company, serving him for nearly three full decades. It's another example of how a character isn't just interchangeable. It was Mark Calaway's perfect suit and McMahon had an eye for the prize in 1991.

The Undertaker, as we know, would go on to create a legacy for himself that still remains unmatched. He's surpassed eras, transcended any status of "babyface" or "heel" and remains the most respected legend in the business today.

It's hard to find a single person that disrespects The Undertaker and its all credit to McMahon and Calaway himself.

In an era where gimmick change and repackaging is the order of the day, the longevity of the Undertaker character is what makes it special.