Producer: Andre 3000
Album: Speakerboxxx/The Love Below

After four rap albums that easily put him in the ranks of the greatest MCs, Andre 3000 went even further left-field and started singing. Some criticized the decision, but most were too caught up with the brilliance of "Hey Ya" (and its music video) to care. The song held down the #1 Billboard position for nine weeks and eventually scored a Grammy shortly after its run on the charts.