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A 16 year old rapper who has...interesting swag and an amazing smile.
Friend #1: Oh, that's Diggy Simmons?

Friend #2: Yep.
Friend #1: He is soooo cute.
by Sky Phillyyy...:) August 09, 2011
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a 16-year old rapper whose father was a part of run dmc. became well known from his family reality tv show run's house. but he is now making a name for himself and he has reached a million folllowers on twitter, been on three tours in less than a year, sold out show, and his highly anticipated album "unexpected arrival" comes out on march 20th, a day before his birthday. with his fans the "jetsetters" behind him, diggy is going nowhere but up like jetsetters do!
Fan "Did you hear that song "do it like you" on the radio?"

Fan B - "Yeah. I did"

Fan "Isn't it amazing it is by Diggy Simmons?"
by fangirl March 04, 2012
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Son of Rev Run. from RUN D.MC. Most of his fans consist of girls between 13-17 who don't know a damn thing about real hip hop. He did not have to work his way up to get famous due to his dad being part of RUN D.M.C. Girls will swear up and down that he still made it on his own, however he didn't have to work for shit in his life.( Any nigga who say was the son of Rev. Run could walk into a record company building, and they would get signed pretty quickly, even if they did not have much talent, just the fact that they were related). It's not that Diggy can't rap for shit, Its just that there are plenty of young niggas living in the hood won't ever get signed, but this bitch gets signed just because of his father. He also has the nerve to come at J. Cole because Cole fucked the shit out of his sister. His disses were pretty weak even though people act like it is "Ether" when Nas came at Jay Z.
J-Roc- Yo, you heard bout that bitch nigga Diggy Simmons
Dre- What about his punk-ass
J-Roc- He tried to come at J. Cole cause Cole smashed his sister.....that shit was mad corny
by Merciless Assassin April 19, 2013
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