This is Dorrough (as in "cream on the inside, clean on the outside" Dorrough) and some guy named Young Lot, who appears to be from Sunnydale. The beat is a sort of update of MC Breed's "Ain't No Future In Yo Frontin", and the song itself is nowhere near as good. What I find interesting is that he seems to have filmed a big portion of the video at the Potrero Del Sol skatepark in the Mission. It's not like he's particularly hip or anything; he is clearly too large to skateboard. What is slightly stranger is that he shows no love for SF's true first skatepark (if you don't count that bowl in Hunter's Point), Crocker Amazon's Chilly Bowl. Being from Vis Valley, apparently, it would make more sense for him to just go up the street and film at the neighborhood spot, no matter how much it sucks.
Big Rich, at it again, pretending that he is already popular, despite the fact that he really is not a good rapper. Anyway, in some unfinished rap music video "plot" point, Big Rich meets up with all his buddies at Raoul Wallenberg High School, but it goes nowhere. Maybe Big Rich wanted to get a last shot at ollieing the Big Four (PS - There's a wiki page for the Big Four!?!?)?
Then again, he's much too fat, just like this picture of what is supposedly a Mac Mall Mac To The Future commemorative skateboard, which you can buy, for $85 dollars at RapBay.
You know, none of you guys got me a birthday present, and I did just snap my board...