Classmates: Kendrick Lamar, Big K.R.I.T., Mac Miller, Lil B, Yelawolf, Lil Twist, Meek Mill, Cyhi The Prynce, YG, and Fred The Godson.
Growing up on MTV, son of legendary, multi-millionaire, Run-DMC rapper Rev Run, Diggy Simmons has the world at his fingertips. While still in high school Diggy started to dabble in hip hop. One of his earliest releases to strike a chord was his freestyle over Nas’ classic song “Made You Look.” Let’s be real, the freestyle was tight. Justifiably so the track launched a bidding war amongst the major record labels. Diggy ultimately chose Atlantic Records, effectively sealing his fate when he signed his name on the dotted line. Atlantic, who has a track record for turning rappers into pop-stars, did just that with Diggy. He’s one of the few legitimate flops in true meaning of the term. With a full court major label press promoting his debut album Unexpected Arrival, the record literally flopped only selling 20,000 copies first week. Which in 2011 was even worse than it may be now. After taking a year or so off, Diggy just released a song featuring him singing. Yeah, this one isn't turning around anytime soon.