Diggy Simmons: New-Age Rap Genius Takes Flight

Diggy Simmons: New-Age Rap Genius Takes Flight

Story by A.R. Shaw
Images by Dewayne Rogers

What would hip-hop be without the Simmons family? Russell Simmons is the architect of hip-hop s infectious entrepreneurial spirit, and his brother Reverend Run, of the legendary group Run-D.M.C., taught rappers how to delve into  mainstream entertainment without losing touch with the streets. And Run s son, Diggy, represents the next generation of the Simmons family to stamp his imprint on hip-hop.


But while he comes from a lineage of hip-hop greatness, Diggy isn t leaning on his connections to make a name for himself. He wants to make it known that talent, not nepotism, is the reason he s on the verge of a thriving career in music.


“I just decided to come into what I wanted to do on my own and figure out different things that I have to do with music by myself,” Diggys says. “It s about making my own sound and doing me. So [Uncle Russell and my father] were never on my back because they knew I wanted to take it into my own hands.”

Diggy is indeed doing things on his own terms. Before he got the chance to have a meeting with a major record label, he used the Internet and social media to build a buzz.


After compiling several notebooks full of raps, Diggy contacted videographer Phil the God through Twitter. The two collaborated to shoot Diggy s freestyle over Nas “Made You Look” instrumental. Within days of its online release, the video went viral. It wasn t long before several major record labels were involved in a bidding war to sign Diggy.

He eventually chose Atlantic Records and began working on his debut  CD, Unexpected Arrival. With two hit singles (“Copy and Paste,” “Do It Like You”) and a successful tour (Scream Tour) under his belt, Diggy has positioned himself to release one of the most anticipated albums in 2012.
Unexpected Arrival appeals to youthful audiences without question, but it also proves that Diggy s lyrical skills are on par with the best rappers in the game.

This isn t child s play. Diggy is more than a teenage heartthrob and he doesn t plan to use his age or famous last name as a gimmick to sell records.
When it comes to rap, he s flying sky-high.

You often talk about being a “jet-setter.” What does that term mean to you?
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.

Every artist remembers one great album that influenced them the most. What album inspired you to pursue a career in rap?
That album for me was College Dropout by Kanye West. I loved everything about it. We needed it at the time. Everything about Kanye was so different. Back in the early 2000s, everybody was being a gangster or somebody that s really hard. Kanye came into the game and gave an album that was just so different and so substantial from top to bottom. And the concept was just mind-blowing.

When did you decide to take that inspiration to the recording studio?

I didn t start off in the studio recording music, I started off writing and that s what it was really about. It was about expressing my feelings through writing my raps; all of the different experiences I ve had and getting that off my chest through rapping. So when I did get in the studio, I wanted to record for a purpose. It started off as something that was fun, and I realized that I wanted to do it for a living.

Take us back to the day you were signed to Atlantic Records. What was that day like?

It was great. What I remember most about that day was that it was the day after my birthday and everybody that I loved was there. I remember the energy and the love in the room was just amazing. It felt like it was the start of something new, and that s what getting signed is about. It s about taking what you do, and then having people with great resources being able to take what you do to the next level.

A lot of new artists don t realize that getting signed is only part of “making it” in music. How much more work needed to be done after you signed your deal?
That s when the grind starts. You don t make it once you get signed whatsoever. That s when you really have to start grinding and putting in the work. Because now you have people depending on you to make great music for the world. That s when you have to work hard and stay true to yourself and make the best music that you can. Even if it s not built in you, you should just look at the things that you need to do to get to where you need to be. And that starts with having a great work ethic and being consistent. Your work ethic has to be greater than your talent level.

What was it like creating your first album?

When I went out to L.A. in January 2011, the first two songs that I recorded made it on the album. I was blessed enough that the process was just so natural and organic. I had the right people around me, such as great producers. I was able to make a real sound for myself. I m so proud. I haven t been so enthusiastic about something in my entire life.

How have you been able to balance your work as an artist with the work you do as an entrepreneur in your sneaker and clothing line?
Honestly, I don t really look at the sneakers and clothes like a business decision that I m making or being an entrepreneur. Creatively, if I love something and I have the opportunity to do it, I ll do it. I love creating and making great things for the culture. I don t feel like it s me being an entrepreneur, even though technically it is looked at as that. It s just me doing more of what I love.

Social media has played a big part in your career thus far. Why is it important for you to remain close to your fans through Facebook and Twitter?

As far as being closer to fans, that s something that s more genuine. If you really appreciate the people that support you and go hard for you, you re naturally going to want to connect with them, so that you can tell them that you love them and that you thank them for their support. I don t think that you should use it just because you want to get further. I do it because I really love the fact that my fans take pride in being a part of this journey with me.

What do you want your impact on hip-hop to be?

I want people to say that I took hip-hop, a genre that people may not always look at in a good light, to the next level. I just want to have a positive outlook on it and reach even bigger milestones and take it to the next level.

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