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Back in October 2011, AllHipHop.com spoke to Diggy Simmons as he was working on his debut studio album, Unexpected Arrival, and riding high on the success of “The Scream Tour” which sold out venues nationwide. Four months later, Diggy has officially finished recording and is now headlining his own “Life of the Jetsetter Tour”.

For the 16-year-old son of Hip-Hop icon Rev. Run, life couldn’t better, and in less than a month’s time, the end result of his influences and hard work will be heard by fans and listeners around the world. After the release of his first two singles, “Copy, Paste” and “Do It Like You”, he has leaned to his more lyrical side and decided to unveiled his new single and video with Jadakiss titled “88” for his fans.

AllHipHop.com spoke to Diggy at the Atlantic Records offices in New York City last week, where he was working on finalizing the CD jacket for Unexpected Arrival, due in stores on March 20. In the video below, he opens up about being the “Jetsetter General”, headlining his own tour, and more:

In this second clip, Diggy talks about his show line, Chiv Culture, if he has any plans to make a return to television, and how social media has helped him as an artist:

Follow Diggy Simmons on Twitter (@Diggy_Simmons). His Unexpected Arrival hits stores on March 20.