1. Dan the Automator
Not a rapper, but the wiz behind more instant-classic hip-hop albums than -- well, more than you've made: as Deltron 3030 with Del tha Funkee Homosapien, as Dr. Octagon with Kool Keith, as Handsome Boy Modeling School with Prince Paul, as Lovage and/or Crudo with Mike Patton (!), and as a producer for everyone from Cornershop to Kasabian to Ben Lee. Also: Gorillaz. Need we say more?
2. MC Hammer
Needs no introduction, really, except maybe you haven't been following his career since his untouchable phase. Quoth Wikipedia: "Hammer became a preacher during the late 1990s, was a television show host and dance judge, is a record label CEO, and as of 2008 works as a co-creator of a dance website called DanceJam, while still performing occasionally at concerts and other social media, ministry and outreach functions. In addition, he is executive producer of his own reality show called Hammertime which airs Sundays at 10 PM EST on the A&E Network." And let's not forget that Purell commercial.
This Vallejo pioneer was hyphy before hyphy was hyphy. What? Right. Took him about a decade to break out of the California scene, first by way of the dirty South, and finally to national radio, albeit only twice (see "Tell Me When To Go," produced by Lil Jon and featuring Keak da Sneak; see also his guest spots on DJ Shadow's critically panned hyphy experiment The Outsider and on the Lonely Island's Incredibad, where he plays Carlos Santana). E-40
owns used to own a Fatburger in Pleasant Hill, and a nightclub. He still owns a designer cognac brand, and remains on the grind: this March saw the simultaneous release of Revenue Retrievin': Day Shift and Revenue Retrievin': Night Shift. Surely at least some of that was reportable income.
4. Too $hort
If the world were fair, Too $hort would get royalties every time anyone used the word "beeyotch." The world's not fair, but $hort has still sold 11 million albums domestically. He also owns Up All Nite Records, whose flagship act, Berkeley quartet The Pack -- featuring newsworthy loudmouth Lil B -- has been garnering, uh, hella press.
Sure, he was born in Harlem, but he did attend Tamalpais High School. And he's been dead since 1996, too, but at 75 million albums sold -- more of them released posthumously than prehumously, and some of them going quatruple quatropple platinum -- his estate still makes serious bank.
Honorable mention: The Coup
Oakland's avowedly communist political rap stalwarts have an anti-capitalist streak longer than the Bay Bridge: see their 1998 Steal This Album (later rereleased, somewhat puzzlingly, as Steal This Double Album). That hasn't stopped them from licensing songs to Superbad and a couple of video games. They'd probably reject any high-grossing rap club that would have them as members anyway, and so much the better -- not everyone gets, as Biggie put it, to blow up like the World Trade.