Diggy Simmons

Sixteen-year-old rapper and 2011 XXL Freshman Diggy Simmons seems to have a bright future ahead of him, but many are wary of him due to his public debut as an MTV reality-show character (see: Run's House), a pervasive feeling of nepotism, and his overly crafted and hyped teenybopper sex-symbol image. The fact is, what other high-schooler gets to work with legends like Pharrell and DJ Premier? Nevertheless, it's hard to deny Diggy's precocious charisma in front of the mike.