Diggy Simmons released his debut mixtape, The First Flight, in 2009. More than 100,000 people downloaded the album from Simmons' blog. Following the album's release, according to Simmons, five record labels showed interest in signing him; he chose Atlantic Records. Early in 2010, Simmons uploaded a video of himself freestyling over the Nas song, "Made You Look". The video became a viral hit and garnered praise from Kanye West, who responded on Twitter: "I knew this kid was [going] to be fresh. I knew it!" Wiki

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