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Raptors HQ Wayback Machine: Pay Oak His Money!

Raptor Legend Charles Oakley has a new book out. You should buy it if you know what’s god for you.

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Basketball: Big Three Jerome Miron-USA TODAY Sports

Toronto Raptors Legend Charles Oakley has a new book out: The Last Enforcer. While Oakley played for the Raps for only three seasons, he was arguably THE key figure in the early Vince Carter-era Raptors earning league-wide respect. Largely because despite being ground-bound, Oakley was pretty much the most terrifying dude to ever lace up a pair of Nikes. Seriously, like half of the league lived in ever-lasting fear they were going to piss Charles off. Oh, and NEVER owe Oakley money... ‘cause that ALWAYS ended badly.

To honour the man who’s presence made the Raptors legit, Raptors HQ has dug back, twenty-three years, into the archives for this tongue-in-cheek piece about everyone’s favourite round-ball ruffian.

(FYI: Google the Tyrone Hill and Jeff McInnes vs Oakley feuds, it’s worth your time.)


So, I was out picking up a new pair of shoes the other day, and, I’m staring at the racks. I’m seeing that Garnett has a shoe, and A.I. (of course) and LeBron, T-Mac, Vinsanity. All well, fine and good.

I keep looking: “Hey, Jordan’s got another new one out, and even Dr. J has a shoe.”

Which gets me thinking…

“Where’s Charles Oakley’s shoe”?

I mean, wouldn’t you buy a Charles Oakley shoe? If only for the fear factor alone? (That factor of course being that Foot Locker sells a list of everyone who doesn’t buy Oak’s shoe to Oak himself. And, then he tracks down every last one of y’all?)

Seriously though — a Charles Oakley shoe? How cool would that be? Wouldn’t the shoe be made of some indestructible cow hide? Like, from the cow who killed four ranch hands when they tried to subdue her — including turning that bolt gun on one dude’s crotch?

Some suggested names for the Oakley shoe:

The: “Charles Oakley is gonna beat the hell out of all y’all 3000”

The: “Air Charles doesn’t have time for your whining”

The: “Chuck Norris is a p***y when compared to Chuck Oak” cross trainer.

All you’d need for the ad campaign is a picture of Oakley. The slogan? “Buy my shoe — I’m right behind you.”

As I sat there, I realized the ridiculousness of my idea… why limit Charles to a shoe? That’s just simple leather and rubber stitched together? It’s practically an insult to the man.

Why not think... bigger? Why not give Oak his own show? It’s just one letter different — but oh, the universe that letter opens up…

Picture this: Oak At Night is a sort of variety thing. It starts with a talk show where Oak rattles on about whatever is rolling around in his head.

Suggested topics:

1) Why dunking is over-rated for 6’9 power forwards.

2) Why a behind-the-back-pass that ends up in row three is actually a strategically valuable ploy.

3) Why just because there’s glass on the road don’t mean there’s been an accident.

I really don’t care what Oak talks about — its guaranteed entertainment. And wouldn’t it be exceptionally amazing to get Oak’s thoughts on, say, Kanye West’s comments regarding George Bush and Hurricane Katrina?

Then the second part of Oak At Night would be a game show. Very much like: “Win Ben Stein’s Money” except kinda exactly reversed.

It would be called: “Pay Oak his Money”

Sure, you could still win a pathetically small amount of Oakley’s cash — but really the key to the game would be you could lose your OWN money to Charles. You’d compete in whatever Oakley came up with that night. Trivia... Karaoke.... Slapping the skin off of Tyrone Hill’s face... You know — usual game show staple stuff.

Then, every time you lost a challenge, the studio audience would shout out: “PAY – OAK – HIS – MONEY!!!”. If you chose not to? You’d be thrown into a bouncy castle. The kind they always have at Kiwanis sponsored events, and Oak would pummel you with a nerf bat. Or, maybe just a bat.

The best part of the show would be when Michael Jordan dropped by, because immediately the stakes for whatever challenge you were performing would jump a hundred-fold. So, suddenly you’re betting on whether you or Oak can toss a Jai-alai ball closer to Hill’s crotch for five-thousand of your own dollars. And, what are you gonna do? Say ‘no’ to Jordan?

Even better would be the fact that Jeff McInnis would be Oak’s sidekick. They’d have all sorts of fun little moments together.

OAK (staring at menacingly at McInnis, who is doing the inane talk-show-sidekick-laughing thing after Oak has just finished his rambling monologue which, by the way, consisted of a full five-minutes on the societal impact of craps): What you doing, Jeff?

MCINNIS (startled): Huh? Nothing Oak. Just laughing.

OAK (stare growing more intense): You trying to tie a ribbon around the old Oak tree?

MCINNIS (looking around helplessly for the floor director): What? Oak?

OAK (The stare is now actually putting divots in McInnis’ skin) You trying to tie a yellow ribbon ‘round this old Oak tree?!?!

MCINNIS (Who now looks like Brett in the “What” scene from Pulp Fiction): Seriously, Oak?

OAK (Standing): You looking at the Oak Fly Girls? You disrespecting a woman who is with the Oak?

MCINNIS (Looking frantically for Dick Bavetta): Please, don’t kill me Oak.

I really can’t see how this show doesn’t become a huge success. It’d be a thousand times better than Jimmy Kimmel’s talk-show. And, that includes all the times he has Sarah Silverman on.

So, I ask you this. Please, write to your local cable affiliate. Tell them you want to see “Oak at Night”, just as quickly as they can design an intimate yet completely generic comfy “living room” setting for Charles.

Because, if you don’t — I’m selling Oak a list that has your name on it.

Oh, and buy the shoes... it’s for your own safety.