From the Jay-Z article in the new issue of Esquire, with my future ex-wife on the cover:

But there is a deeper significance — a racial philanthropy — that perhaps neither [Jay-Z nor his enabler Steve Stoute] intended. Jay-Z is black black. He is old-school double-dark-chocolate-chunk black. He is black the way Labatt is blue. He is not white black, Barack black, like our president. Or the kind of black that doesn't curse and deplores the n-word, the genteel black, like Oprah. He is, arguably, the first black-black guy to cross over into Oprah-land and Bill Clintonworld without making the Oprah-sized no-look-back forward flip that means you're selling not necessarily your soul but perhaps something fleshier, a little more external.

The author suggests that Jay-Z's phenomenal (business) success is significant in part because he's more authentically black than other uber successful blacks, like Oprah Winfrey. But is Jay-Z really blacker than Oprah Winfrey?

The case for Jay-Z being blacker than Oprah:

1) Jay-Z is from the Marcy Projects.

Oprah Winfrey was born into abject poverty in rural Mississippi, but she's an old-ass woman. That was back when all black people were born into abject poverty in rural Mississippi. Jay-Z is no spring chicken himself, but he was born into a time when black people who had the sense god gave geese had already begun to escape the projects, thus setting the stage for the crack era. I'm not gonna lie - I've driven past the Marcy Projects (on the way to sniff some blow in Williamsburg, natch), and they didn't look that dangerous to me. Would I have gotten out of the car and taken a foot tour? Obviously not. I'm just saying. But I can only imagine what it was like back in the 1980s.

2) Jay-Z used to sell crack.

Remember when your parents told you that if you sold crack you wouldn't amount to shit? No but really, I dutifully avoided selling, unless I just so happened to have a shitty dimebag that one of the kids at my job wanted, and all I've got is this buskit. Jay-Z used to sell crack as if it was going out of style, and now everyone just pretends as if he didn't. When Jay was moving weight, back in '88, Ronald Reagan was on TV showing off a bag of crack he supposedly bought down the street from the White House, but he probably just had delivered to him by the CIA. Now, Jay-Z has been known to kick it with Bill Clinton, at the barbecue restaurant, which probably isn't as good as the barbecue restaurant where I used to work.

3) Jay-Z has daddy issues.

People who actually grew up with their fathers, i.e. most white people and maybe 10 black people, hardly have any memories of meaningful interaction with them, despite the fact that they lived under the same roof for upwards of 20 years, if not longer than that for some of us sorry sacks of shit. Jay-Z's father walked out on him like a showing of The Inkwell, and he can't shut the fuck up talking about it, as if he actually missed something. People who work for a living were paying the rent anyway, so if anything, Jay-Z's father leaving the house just freed up some space. Blaming your absent father for your own personal failings is arguably the quintessential black behavior.

The case for Oprah being blacker than Jay-Z:

1) Oprah never has been able to get her weight under control.

All that money for private chefs, personal trainers and what have you, and Oprah still can't keep her body in decent shape. That's a black woman for you. I remember watching Oprah once, a long, long time ago, after one of those time when she'd gotten skinny. She was talking about how she'd go on emotional eating binges, like Luther Vandross. Something would upset her, and she'd just go to town. But you have to think at least part of it had to do with what she was eating. You can't get that fat just eating arugula, and other shit rich people eat. It's the same concept as trying to get drunk off of beer - you'd fill up before you did any real damage. Luther Vandross had the infamous Luther Burger. If I had to guess, I'd say Oprah is a big fan of fried chicken.

2) Oprah used to smoke crack.

One of the few other times I've seen Oprah was that time she admitted to being and ex- (?) crackhead. My mom told me about that shit, and a friend of mine and I rushed home from school to check it out. Oprah claims that some guy she was with forced her to do it, Rick James-style, but later I read that she was the one who introduced him to crack. As if it matters. The important thing is that Oprah Winfrey had the money to do drugs other than crack, but she opted for crack. Oprah Winfrey has been the host of her own talk show since the early '80s, and she was the anchor of the evening news or some shit before that. Her show went into syndication in the mid '80s, and you know what that mean. Mo' money, mo' problems.

3) Oprah Winfrey is 55 years old and has never been married.

What's more black than a woman with a shedload of money who can't find a man? And I do mean a shedload. I checked the world's most accurate encyclopedia just now, in researching this post, and it says she's worth $2.3 billion. Her salary is supposedly $385 million. She probably makes more money in a minute than I'll make in my entire life. If Oprah Winfrey woke up with Jay-Z's money, she'd jump out a window. And yet, Oprah Winfrey remains single. Yeah, there's that guy Stedman, but he's obviously on the DL. She just pretends that's her boyfriend, because white people don't like the idea of famous people who aren't in relationships. Supposedly, that's why Tiger Woods' handlers made him marry his nanny, when he obviously wasn't ready to settle down. Oprah would have just found a guy to marry, if only she could. Meanwhile, when's the last time you heard of a white woman with $2.3 billion who had to take up with a closet case, just so it would look like she could find someone to be with? I rest on your face.

Conclusion: Oprah is clearly blacker than Jay-Z, amirite?