Photo by J.Shotti for GLMJS Photography

At only age 14 most of us can not say that we’ve done what Diggy Simmons has done thus far in his young life – a fresh clothing line on the way, thousands of blog followers on Life of a Jet Setter, and now a budding hip hop career. Last month, after dropping a freestyle over Asher Roth’s She Don’t Wanna Man, Diggy got an idea to put out a mixtape and did just that. Little did he know that The First Flight Mixtape would gain such notariety on the internet – capturing the posts of many blogs but also spur talks of him doing some major things in hip hop for 2010 and going forward. We at WIMH were fortunate enough to get an interview with this young talent as he enters a world he is familiar with in being Hip Hop royalty by way of his father Rev. Run and Uncle Russell Simmons, but had not yet explored. That which spurred him to prove something to many…

WIMH: So of course tell us about how you have the internet going nuts with this The First Flight mixtape – how did it come about? who did you work with on it?

Diggy:  So a lot of people don’t know I’ve been rapping since I was 5 and stopped when I was like 10. But I still continue to write. Then this summer I got back into recording, just like tracks over instrumentals on Garage Band and then I did a remix to Asher Roth’s She Don’t Wanna Man and I released it around July and it got major buzz  – acutally endin up on the radio in LA too. So my boy heard it and he was like yo u need to release a mixtape so I took it into consideration, thought about it and then just got to working on it seriously by myself. No one knew except for the producers I worked with which were Young Jerz, Black the Beast, Neako, and Natural Disaster.

WIMH: So you just hooked up with the producers via the internet and other outlets?

Diggy: I knew Young Jerz and Black the Beast before and connected with Neako and Natural Disaster along the way.

WIMH: No doubt…so I remember you stating, you had something to prove, what were you looking to say or prove with the mixtape? I know a lot of people out there thought you had your father helping you out but that wasnt the case at all.

Diggy: I’m a real independent artist – I don’t have someone that schedules my performances, interviews etc. I just do it on my own and with this mixtape a lot of people were skeptical because they were 99% sure they knew I was going to be saying  “Louis Vuitton this and Rolls Royce that” when that wasn’t the case at all.  So my point was to prove that – No I’m not what you think I’m going to be and do what you think I’ll do. I definitely shocked not only people but my own family.

WIMH: Good stuff…I think people like myself who are older were impressed that you weren’t just talking about the money, cars, and the clothes…so that was good to hear…

Diggy: Thank you.

WIMH: Who are your musical influences? If you could rap alongside of some artists who would they be?

Diggy: My influences consist of Lupe Fiasco, Andre 3000, Q-tip, Mos Def, Kanye West and some others – just real lyrical poets.

WIMH: Those are some great artists all around their music reaches many people…So growing up in hip hop and that culture…How have you seen it change? Do you really think hip hop is dead?

Diggy: No not at all because you have upcoming people like Jay Electronica, J.cole etc. that are trying to bring Hip Hop back to the real content as it was – like I am.

WIMH: Yea man, Those Exhibits Jay is putting out our epic and J.Cole is definitely a beast on any track these days…So of course, this blog is called WIMH, so…What’s in YOUR Headphones Diggy? Who are you listening to currently? Anything outside of hip hop and rap that you listen to?

Diggy: Right now, What’s in My Headphones Hip Hop-wise are really all the names I mentioned before (Jay Electronica, J.Cole) and some others, and I’m into a variety of genres such as alternative music like N.E.R.D. and MGMT, Lykke Li just to name a few.

WIMH: A lot of people sleep on Lykke Li…so I gotta ask you in growing up as the son and nephew of two of hip hop’s pioneers, is there any added pressure for you to be successful?

Diggy: Yes, but I’d rather have that pressure then any other. But when I work I block out my last name and it’s just MY stage name in which I use – “DIGGY”.

WIMH: Thats dope…well at your age I was nowhere near where you are…you’re a good example and role model for your peers as going out and getting what you want…

Diggy: Thank you man that’s all I’m trying to do – let the young people know that you can do it too.

WIMH: How is it kind of growing up in the spotlight of a reality tv show? I mean we’ve seen you grow up into a teenager now…

Diggy: It’s the BIGGEST gift and the BIGGEST curse.

WIMH: Why do you say its the biggest curse?

Diggy: Because of people’s pre-conceived notions of me and what they think I am: spoiled, a brat, sheltered etc.

WIMH: Yea I can see that and that is unfortunate…so tell us about your clothing line, last I remember seeing/reading was that you were working with Pharrell, correct? What have you learned from Pharrell in that mix between hip hop and fashion?

Diggy: Pharrell is my mentor in fashion, he’s not working with me on the line but he supports me in all I do and he just gives me the best advice whether it’s me not being happy with my marketing to my designs. One of the things I’ve learned from him was the equivalent between fashion and music. Which is powerful because people say anything you do is connected with the next thing. So I learned if your gonna do something apply your self and do it all, be the best at it. If your a rapper and you know what you love why wouldn’t you make production? So everything Pharrell teaches me is very meaningful.

WIMH: Good life lessons too…Dude, your fashion sense is rare for someone your age…who in fashion do you draw inspiration from?

Diggy: Peoples work or there personal style?

WIMH: Speak on both.

Diggy: Well if you start at street wear, Nigo is a great name and A Bathing Ape is stamped in history as far as street wear goes because If you look at these new school street wear brands such as Billionaire Boys Club/Ice Cream, Original Fake and many others – Nigo really paved the way for that. As far as Couture work goes I’m a fan of the great Karl Lagerfeld outside of his work with Chanel – his personal style is iconic. I’m also a big fan of Dior Homme and Kris Van Assche because they help bring sneakers into the fashion game. I’m also a big fan of Marc Jacobs beyond clothing with his creativity and the ideas he brings to his own brand and his work with Louis Vuitton each year is brilliant on and off the run way. There’s more but that’s just a few people to sum it up…

WIMH: Yea i know that was kind of a open ended question, but I see that you are definitely a student of your craft as well..

WIMH: Alright you gotta choose…hip hop career or your clothing line?

Diggy: I haven’t gotten to that stage of thinking yet nor will I be because the moment I think it is the moment I’ll turn to one

WIMH: I can respect that…

Diggy: (laugh) Yea bro…

WIMH: No, that’s a good answer (laugh) your political, I’m the same way

WIMH: Ok…its a freestyle battle – who wins between you and your pops? Gotta have faith in your skills to challenge pops right? (laugh)

Diggy: Of course but i don’t even know if he freestyles, I think he just kills it with the pen. I’m the same way but I practice (freestyling) and catch my self saying some real witty things out of the blue.

WIMH: No doubt, no doubt…(laugh)

WIMH: Ok, last question, with so many paths or routes that you can go in the future…where do you see yourself in 5 years?

Diggy: I’ll be 19 so I’ll definitely have two albums out by then, signed, my clothing line out and successful along with all the other business ventures I have on the table now. Pretty much just very successful and settled along with being on some tours. And more than that man time will only tell

WIMH: great bro…you are off the hot seat my friend…thank you for taking the time out  and talking with us at WIMH…

Grab Diggy Simmon’s Mixtape The First Flight here…and check out Life of A Jet Setter…

This is WHAT’S IN MY HEADPHONES…

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