On Chappelle's Show, when that was still around, there was a satirical segment about Wu Tang Financial, which included the line: "You need to diversify yo' bonds, nigga!" Kind of a cheap laugh, yeah, but funny.
Anyway this isn't a joke: WuChess, a new hip-hop-meeta-chess site from the Wu crowd. As TechCrunch points out, the site charges money to use. Is that a problem? Maybe not. Lots of the big chess sites charge: Playchess.com and the Internet Chess Club among them. FICS (Free Internet Chess Club) doesn't charge, which is what I use... but seriously, it's not ridiculous to charge for a chess site.
The tough part won't be the fee, but in trying to replicate the thrill and electricity of chess in the park. That's going to be tough without the hustling, money, and everyone all shuffling about, but hey, still a cool idea. Another thing that's key to hip-hop chess, in my opinion: not saying "check" and actually attempting to take the king, which never happens online or in any legitimately sanctioned chess. And courtesy of Valleywag, here's a hip-hop chess video.