Wait A Second: Is Charles Oakley Cooler Than Charles Barkley? Let's Think About This

Charles Oakley's comments about Charles Barkley have us wondering: in a contest of two of the coolest NBA players ever, who wins?

Who would you rather hang out with on New Year's Eve: Charles Barkley or Charles Oakley? Obviously, there's no wrong answer to that question. But if you had to choose...

Okay, let's set the scene. A little more than a week ago, Charles Oakley appeared on a radio station in Miami to talk about the NBA. And when anyone talks about the NBA, particularly with a Miami radio station, it's only a matter of time before talk turns to LeBron James.

Now, just about everyone else in the basketball universe took this summer as an opportunity to bash LeBron for either a) taking the easy way out b) betraying Cleveland in the worst way possible C) making an ass of you and me (and him) for assuming that The Decision was a good idea, or d) All of the above. Charles Oakley, though, predicted in May — two months before any decision — that Bron would jump to either Chicago or Miami, and later, openly told reporters that LeBron shouldn't go to the Knicks. As he said during the buildup to James' decision:

"I can’t tell him to go to New York. New York treated me bad… When I go to the Knicks games, do you know that they have somebody that follows me around to see what I say to the press?"

And when Oak was asked recently whether he thought Knicks fans had a right to be angry with him for telling LeBron not to go to New York, he offered this totally badass response:

"My thing is, I’ll be real with people and if you’re a sports guy and ask me something, know what you’re talking about when you’re talking with me because I’m gonna expose you because I’m not a bullshitter. I know what I’m talking about. If somebody told you something and you take it and run with it you don’t know facts. If you don’t know facts you shouldn’t even interview me because I’m gonna expose you because its bullshit. It is what it is."

But that was just the beginning. When Oakley was asked about Isiah Thomas, talk somehow turned to Charles Barkley, and that's when things got real:

"My thing is, when Barkley played basketball, he didn’t practice, he wasn’t a leader, he wasn’t this or that, he just had natural talent so he got chosen to the Dream Team, All Star team because he had the talent and he was the franchise player on the team. Him criticizing all those other guys, he did the same thing when he was young. As soon as they do something wrong, he criticizes them, that’s wrong. He wasn’t real to the game. Let the guys speak out who are real to the game. He talks like a player and I will give him that, but for him to comment about this and being a professional, he wasn’t all that."

Umm... SHOTS. FIRED.

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Is it possible that the two coolest NBA players of this generation actually hate each other? Maybe, right? That certainly didn't seem like friendly jest. If they do hate each other, does it all trace back to some love triangle with Michael Jordan? I like to think so.

More importantly, if these two guys are going to force us to choose sides, who do we choose?

Let's think about this from every angle.

WHO HAD THE BETTER CAREER? This one's easy. Barkley averaged 22 and 12 over the course of his NBA career, including playoff averages of 23 and 13, and won an MVP in 1993. He never won an NBA Championship, but he was also good enough so that we all measured him against guys that did. Oak, on the other hand, came of age on some of the early Bulls teams with Michael Jordan, and then starred as an enforcer for the legendary Knicks teams of the '90s. He never won a title either, though. And yeah, a lot of what Oak did isn't reflected by his stats, but that can only compensate for so much.

Barkley's best year, in 1992-93:

52% FG, 25.6 PPG, 12.2 REB, 5.1 AST

Oakley's best year, in 1993-94:

47.8% FG, 11.8 PPG, 11.8 REB, 2.7 AST

So when Oak sneers and says "he wasn't real to the game" or "he talks like a player" it has to be said: Barkley was a lot realer than Oakley ever was, and as players go, then or now, you're not going to get much realer than Charles Barkley. ADVANTAGE? Barkley, big time. 

WHO HAD THE BETTER BACKSTORY? This one's closer. Barkley emerged from a tiny town in Alabama and wouldn't have been recruited to play college basketball at all if not for a scout from Auburn that saw him dominate the Alabama state tournament, and discovered "a fat guy... who can play like the wind." He continued to struggle with weight issues throughout college, and at no more than 6'5", he wasn't exactly the prototypical NBA power forward.

Oakley, on the other hand, was even less heralded coming out of high school. Despite playing high school basketball in Cleveland, Oak wound up at tiny Virginia Union. And where Barkley's biggest question marks were size-related, Oak faced questions about his polish. And they both dealt with their deficiencies the same way: basically, by being tougher than anyone else.

Barkley never really got his weight under control, and Oakley never developed much of a finesse game, but they both kicked ass anyway, beating the odds, and beating the crap out of more gifted opponents. That's why we'll always remember them fondly. ADVANTAGE? Tie.

WHO'S BETTER FRIENDS WITH MICHAEL JORDAN? Well both Chuck and Oak share Michael Jordan as a best friend, although you get the feeling Jordan respects Oakley more. Where MJ might take endless shots at Barkley's weight or work ethic, it's hard to imagine him saying something like that to Charles Oakley. ADVANTAGE? Oakley.

WHO'S MORE ENTERTAINING? No-brainer, again. We don't need to re-hash why Charles Barkley's the most outstanding analyst on television, and the unofficial National Ombudsman. He's awesome, we know. But while we're here: did you know Charles Oakley had a cooking show?

I'm not saying Oakley could ever match Barkley's charisma measure for measure, but if somebody gave him the chance, I bet it'd be a lot closer than you think. Are you envisioning a late-night cooking show that incorporates elements of John Salley's Story Corner and random, famous friends of his like Michael Jordan and Tiger Woods? Maybe that's just me. ADVANTAGE? Barkley, but it's closer than you think.

WHO'S SCARIER? Maybe the Chuckster had a fear factor during his playing days, but even when he's blasting someone like LeBron, he does it all with a self-deprecating smile that instantly cuts through any tension. As for Oakley? Well, he's not the guy you want to piss off. Ever. Charles Barkley wrote a book called I May Be Wrong, But I Doubt It. If Charles Oakley ever writes a book, it should be called, I May Be Wrong, But I Will Whoop Your Ass.

Remember his section in our NBA feuds article from earlier this year?

After Sixers' forward Tyrone Hill failed to pay a gambling debt of $54,000, then-Raptor Charles Oakley waded into the 76ers shootaround in Toronto and pegged a basketball at Hill, nailing him right in the head. ... Later, when asked about the debt, and whether it ever got paid, Oakley wouldn't say, except that the fee had been doubled. As Oakley told the CBC, "Everything in life is double. If he didn't pay me $108,000, he didn't pay me."

ADVANTAGE? Oak. And remember, everything in life is double.

WHO SEEMS LIKE MORE FUN? Well you have this picture of Oakley...

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...or you have my encounter with the Chuckster at the TNT party over All-Star Weekend:

Barkley's just the coolest guy in the room. ... Watching him for a few hours, it's clear that none of his on-camera stuff is schtick. And even though he could have been at any party in the city, he was hanging out and partying with co-workers for the night, dancing with Cheryl Miller, mouthing the words to old school rap, and just being the life of the party. He's got the biggest personality in any room, and yet, he takes care of the little people.

By all indications, he spends his nights buying drinks for people, talking to whoever seems interested, and having as much fun as possible. Then again, it speaks volumes that people like Jordan and Jay-Z would hang out with a supposed NBA journeyman like Oakley. He must be awesome, right?

ADVANTAGE? I'm tempted to side with Barkley here, but who really knows what kind of ridiculous parties Oak and Jordan have been throwing for the past decade? We'll call it even.

WHO WOULD YOU RATHER SPEND NEW YEAR'S EVE WITH? Really, the answer depends on how you're spending New Year's Eve.

If you're going to be at one of those chaotic open bar parties in a hotel ballroom, surrounded by skeevy hangers-on and/or insufferable douchebags, then you'd obviously choose Oak, a wingman that'd single-handedly scare off any unwanted interlopers AND charm any bartender into feeding you drinks all night, not to mention charming a few young ladies. Come to think of it, Oakley's probably the best wingman in human history, narrowly edging out Bobby Kennedy (for his performance during the Cuban Missile Crisis), Will Hunting (for this scene, although he did steal the girl there), and, of course, Goose (RIP).

But what if you don't have plans for New Year's? Find Charles Barkley. He's a one-man ticket to an open bar, chaos will find you wherever you go (in a good way), and you'll inevitably attract the same type of women you'd find at your garden variety $100-a-ticket New Year's party. Watching the Chuckster hold court on New Year's eve would be enough entertainment all on its own.

Bottom line: if you spend New Year's Eve partying with either Barkley or Oakley, you're pretty much guaranteed to have the best New Year's of your life. ADVANTAGE? Everybody wins on this one.

FINAL VERDICT? As you can see, it's pretty much even across the board. I mean, what'd you expect? It's like comparing Batman and Superman. They're both totally awesome.

What Oak lacks in charisma and celebrity, he makes up for with intimidation and sheer badassery. What Barkley lacks in intimidation he makes up for with a basketball resume that's almost entirely beyond reproach. We're choosing between the National Ombudsman and Best Wingman of All Time.

But here's the thing: as cool as Oakley is, he's still just a regular guy, and his greatest claim to fame is being friends with Michael Jordan. There are plenty of pro athletes that also happen to carry themselves like John Shaft, and they're all awesome.

There's a difference between being cool and being truly larger than life, though. And that's the Chuckster. He may be all talk, as Oakley said, but his talk is entertaining as hell and generally pretty accurate. He's a one-man show that happens to be one of the best basketball players ever to live, and unlike Oakley, you never get the sense that he takes himself too seriously. Don't get me wrong; Oakley's the man. But if we have to choose a side between these two, you gotta go with the Round Mound of Hilarity here.

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Now, just to prove why both guys are great and ultimately cut from the same cloth, here are some of the best quotes from both Barkley and Oakley. Try to guess who said what. Answers at the end.

A)  On being benched: "I'm cool with whatever. I'll just keep eating my bread, sipping my soup and serving my time. But the chicken is going to lay some more eggs one day."

B) On flagrant fouls: "Oh well, that's basketball. It used to be basketball. I don't know what it is now."

C) "I always laugh when people ask me about rebounding techniques. I've got a technique. It's called just go get the damn ball."

D) "If it ain't broke, don't break it."

E) "Krispy Kreme might be the greatest invention in the history of civilization when they're hot."

F) "If you go out with a girl and they say she has a great personality, she's ugly. If they tell you a guy works hard, he can't play a lick. Same thing."

G) On firing NBA coaches: "If you have a horse that isn't winning any races, sooner or later you have to get a new jockey."

H) "Somebody hits me, I'm going to hit him back. Even if it does look like he hasn't eaten in a couple weeks. I thought he was going to pull a spear on me."

I) Explaining a flagrant foul: "You got to know when enough's enough. You want to rob the bank, but you better not be complainin' when you get caught. In my day, a guy who jumps that high with that many tatoos, he would've wound up sitting on the floor at least once."

J) On NBA entourages: "They're like contracts. Everybody's got one. Some are just bigger than others."

K) "Every time I think about changing a diaper, I run a little bit harder and a little bit faster to make sure I can afford a nanny until my daughter's old enough to take care of that herself."

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Answers to the best pop quiz of all time: A) Oak B) Oak C) Chuck D) Oak E) Chuck F) Chuck G) Oak H) Chuck I) Oak J) Oak K) Chuck

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