Quoted from vid1900:Sadly, the only rap group with both the look and the following big enough for pinball is ICP.
And the FBI’s ‘2011 National Gang Threat Assessment’ stated that ICP's followers (Juggalos) were an international gang.
While I don't enjoy ICP, I agree with your opinion. They have a bizarre following that spreads way farther than most folks think. My cousin for example, is a middle aged white guy with a lot of disposable income (perfect demo for pinball). He is also an adamant juggalo, although you wouldn't know it unless you looked through his CD collection or saw him at a show. He isn't into pinball but I can guarantee that if an ICP pin was produced, he would be one of the first guys on the pre-order list. It seems like a large portion of their fanbase doesn't care much for the actual product, but follow a mentality of "If ICP likes it, I'll buy it!"
Besides them, I don't see a rap themed pin being successful simply due to pinball collector demographics. That being said, if pinball was in the same position today as it was 20 years ago, you can bet your bottom dollar there would be rap themed pinball games. The genre itself is incredibly pervasive and has managed to place itself within most areas of American society and pop culture. People can knock it all they want but rap is now a well established and influential form of expression that has spread across the globe. Similar to the emergence of rock and roll, rap music has evolved beyond mere entertainment, into the world of political expression and protest.
If rap had hit it's stride a few years earlier, or if pinball had remained a viable market (in terms of income generated from coin-op and routed games) for another decade, I'm positive we would have seen a few rap inspired games, even if it only was something like the Beastie Boys.