20. Wiz Khalifa
Wiz Khalifa, the man who put Pittsburgh on the rap map, was once lost in his own world. After partnering with Warner Bros. Records in 2006, Wiz found middling success, with just one song ("Say Yeah") charting in 2008. He and the label split not long after, and Wiz set about to see if he could do what the label couldn't: promote Wiz Khalifa.
Interestingly enough, he found himself in layers and layers of smoke, and realized that he was home. Mixtapes like How Fly and Burn After Rolling, and the album Deal or No Deal were perfect warm-ups for the hugely popular mixtape, Kush & Orange Juice. He consistently toured sold out theatres across the United States, and an enormous ground-roots fan base was ready to celebrate when he signed a joint venture with Atlantic Records.
By the time Wiz's single "Black and Yellow" zoomed straight up the charts, Wiz couldn't even remember that he was ever associated with Warner Bros. Either because he'd made it doing things his way... or because he was super baked.