We have been covering VERY closely the relationship that Bill Gates has formed with the hip-hop community though his Microsoft Zune marketing campaigns. While Steve Jobs and Apple have done relatively little with hip-hop promotions, Gates and the Zune have gone full force signing everyone from Bun B, Keri Hilson, Common, N.E.R.D., Nelly and Kidz in the Hall with deals ranging from concert promotions to TV commercials. Here is an overall look at these Zune hip-hop promotions and ad campaigns.

So how has the aggressive marketing and campaigning worked out for Zune? Has the millions of dollars spent against the “urban”/hip-hop fan paid off? Well let’s put it this way…Microsoft’s latest report shows Zune dropped an astounding 54% last quarter. In response to the drastic fall in sales, Zune marketing head Adam Zohn states:

“Everyone knows that the economy is not what it was a year ago and that is hurting some folks. We are in a position where the category is also shrinking. So I think those are things that affected everybody’s sales, including Apple.”

If that were the case, then why did Apple and iPod sales only drop 16%? Clearly someone is at the losing end here and it’s sure not Apple. So is it hip-hop’s fault? No. Too often marketers assume that they can capture this lucrative urban market just by paying a bunch of hip-hop artists to promote their product and everyone will follow suit. Problem is “we” are a lot smarter than most companies think. Or I’d like to think we are. Let’s just be glad those Kanye shutter shades were only cool for about two weeks.

Until then, Microsoft should probably hold back on those Zune hip-hop marketing dollars and maybe create a t-shirt line with artists instead. Wait…they already did that too. When will they learn?