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14 Years Ago, Vince McMahon Tried to Give Away $100,000 and Got RickRolled Instead

Vince McMahon's Million Dollar Mania gave us a lot of delights, as WWE's Chairman attempted to navigate telecommunication. Once, on live TV, his ass got Rickrolled.

Today is an incredible day in wrestling history. It’s not the anniversary of a huge main event or a shocking defection. It’s not that it’s the day Stone Cold “took his ball” or the day Harley Race captured another World Championship. It’s not even that it’s Buff Bagwell’s birthday AND Tamina’s birthday. No, today is very special for a different reason.

We’re no strangers to love

You know the rules and so do I (do I)

The year was 2008. Something very, very bad had happened and WWE viewership was plummeting. Vince McMahon was desperate to drive up ratings for Monday Night Raw, and knew his own value as a draw for television audiences. This is why we had poorly timed, phony limo explosions (though they did trick a certain future president) and a whole who-is-my-son saga that went truly nowhere besides some silly leprechaun antics.

Desperate for anything, Vinny decided that giving away money on television was the way to do it. Thus, Vince McMahon’s Million Dollar Mania was born.

McMahon’s Million Dollar Mania

On Raw, the announcers would reveal a special password at the start of the show. Then, Vince himself would dial a number, live on television, in front of an arena of thousands of paying fans. If whoever answered knew the password, they would win the big prize. “Literally nothing could go wrong,” Mr. McMahon breathily whispered to a whole room of people that said yes to this.

Inside, we both know what’s been going on (going on)

We know the game and we’re gonna play it

Watching 62-year-old Vincent Kennedy McMahon legitimately operate a telephone? Now that was compelling television.

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There’s a whole ritual an old person goes through to use a telephone. You have to get your glasses, and your dialing wand, and a piece of paper with numbers on it, and unless it’s a rotary, then there’s always a chance of the wrong number being pressed.

And if you ask me how I’m feeling

Don’t tell me you’re too blind to see

And this isn’t even 112-year-old, pink-eyed, legally blind Vince. This Vince was still regularly wrestling actual matches and pontificating on his Herculean, protuberant physique and bulbous grapefruits. This Vince still had some wherewithal.

But there he was, grinning like a Ricky Gervais character, as he went through the whole telephone ritual, multiple times, on live television in the time it took to watch a single Umaga match.

A full commitment’s what I’m thinking of

You wouldn’t get this from any other guy

Vince McMahon Gets RickRolled

Yes, there were often hangups and misdials. Vince couldn’t see the numbers and couldn’t hear the callers. But one thing he was not expecting was the classic RickRoll.

In 2008, on the internet, you could not escape an intriguing link or an eye-catching YouTube video that instead led you to the Rick Astley classic “Never Gonna Give You Up” when you least expected it. Even then, it was a tired joke.

But to see it happen to Vince, with the long dial, and the cheater glasses, and the declining ratings, and the network pressure, and the thousands of people in attendance and the millions of people watching at home.

Eventually, the whole thing ended with the Raw set falling on a weeping Vince McMahon, and then Trump took over or something. It was a very bad time to be a wrestling fan. Unless, you were one of the lucky winners…

Who Won McMahon’s Million Dollar Mania?

McMahon Million Dollar Mania Winner Peter

Like Peter, who won $75,000 of Vince McMahon’s fortune. Money that would have been used on a tanning bed or hush money, instead went to Peter’s farm and novelty t-shirt collection.

McMahon Million Dollar Mania Winner Guy

Or Guy, who bought himself and his wife a new Ford F-150.

McMahon Million Dollar Mania Winner Jordan

And beautiful Jordan, who used his winnings to finance this incredible Billy Joel tribute band, The Shirt and Tie Stiffs.

And the guy who RickRolled Vince McMahon?

McMahon Million Dollar Mania Winner Daniel RickRoll

That would be Daniel, who stood up for WWE and re-invested his money into replica belts and WrestleMania tickets.

This bad segment gave birth to a legendary moment and changed a few lives for the better. Vince McMahon still pops up from time to time, but isn’t asked to do anything beyond grumble, “I WANT MY EGG.” And the ratings are lower than ever.

And Vince’s response? He’s actually bringing Million Dollar Mania back this summer, and if you’re one of the brave few who can watch Raw in its entirety every week, you can sign up here.

About the Author

Brett Davis

Brett Davis is an Andy Kaufman Award-winning comedian best known for a series of misguided projects like The Podcast For Laundry, The Special Without Brett Davis, and currently hosting WFMU’s Wrestling Club with Darren & Brett, a podcast about the thing.