25. Jay-Z (2 awards from 69 nominations)
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Jay-Z is a living legend in the hip-hop music scene. In fact, he is one of the few artists who took hip-hop music to the bank and made a fortune (then built an empire) from his recordings. Surprisingly, though, Jay has only won 2 Billboard Music Awards despite receiving 69 nominations over the years. He won his first BBMA in 1998.
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