Diggy Simmons covers the latest issue of Rolling Out. In the cover story, the 17-year-old rapper discusses his influences, inspiration and what it means to be a “jet-setter”:
It’s not the traditional definition of what jet-setter is in the dictionary. I define jet-setter [as] being you [and] not caring about what other people think about you. It’s all about expressing yourself freely.
Diggy’s debut album, Unexpected Arrival, is in stores now. Check out video footage from his Rolling Out cover shoot below.
Diggy’s Rolling Out Cover Shoot











Yikes! That picture of Diggy looks like a cross-dressing diesel dyke. No offense toward lesbians but SERIOUSLY?
I love Diggy, he’s hope for the future! But I can’t help but notice he has a big nose! LOL. Still love him
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diggy is really talented i hope he doesn’t make fame get to his head and hopefully keep staying true to himself
I admire Diggy for being different in a good way he knew what swag was real swag was since he was little, he grew up so fast. I appreciate how he is able to keep it fly but not hood, untasteful and unprofessional. Keep up the good work Diggy your a great role model.
Love this kid
different?!! to be truthfull he is copying Drakes style
When he starts harmonizing on his hooks, then maybe we can say he’s copying Drake’s style, Drake is a copycat himself.
Who has copied all the other sing-song rappers before him like Bone and so forth (Drake). I understand the comparison you are making but you also have to realize is this what he wants to do, like is he a fan of that style, or is this what labels and producers are telling him to do? I just heard Diggy’s lil’ song on the radio recently and it’s cute. He has a market and I hope he does well for himself.
Diggy has had his own style since he was on Run’s House (2005). BEFORE Drake existed as an artist (2006) and was on Degrassi. Drake’s Degrassi career started in 2001… before we even knew he had swag. How can you even compare the two? Both of these musicians are talented and different in their own way. Coming from a fan of both.
lol funny
I think Diggy is headed in the right direction. Keep it up!
He’s blessed
everybody stay off diggy and drake please leave these youngmen alone and let them do them shout out to artist/model diggy’s wife jessica jerrel-simmons and their beautiful baby on the way i wish you all a blessed journey together and drake and his beautiful fiance artist/model/designer rita ora many beautiful journeys together..team diggy & drake all day over everything always
everybody stay off diggy and drake please leave these youngmen alone and let them do them shout out to artist/model diggy’s wife jessica jerrel-simmons and their beautiful baby on the way i wish you all a blessed journey together..