He started making mixtapes in 2002, and in 2005, through a mutual friend, was introduced to Grammy-winning producer 9th Wonder. The North Carolina native was won over by the upstart MC's talents, and readily sent him beats to record over—which would soon become 2006's Cloud 9: The Three Day High, a mixtape that launched Sky into hip-hop's consciousness. His deft wordplay, confident delivery, and vivid imagery were all on display. Fans continued to flock following Cornerstore Classic in 2007 and 2009's Power of Words, each mixtape again showcasing Sky's skillset as a hood poet.

It was September 2009's The Salvation, though, released through Jamla/Duck Down, that solidified the rhymeslinger into an elite class. “It all was leading up to The Salvation,” he says. “That was the album I had been planning since I was nine years old.” Landing at No. 14 on the Billboard Top 200 charts, the critically acclaimed release stood on a cohesive and engaging sincerity that explains the sizable fanbase Sky has cultivated.

Still riding the wave of his debut, Sky returned in July 2010 with Live From the Tapedeck, an album produced entirely by !llmind. The summer of 2011 brought The Great Debater, a free mixtape of album-quality material that Sky treate