Diggy Simmons: Hip Hop's Youngest Old Soul

Aside from the Jacksons, there aren’t many families in music who have had more of an impact on pop culture than the Simmons clan. Russell is one of the founders of Def Jam, a timeless and storied institution in music industry history. His brother, Joseph (known to the world as Rev. Run), is a member of iconic trio, Run DMC, and the inspiration behind the hit television show “Run’s House.” Seemingly next up to bat is Run’s son and Russell’s nephew, Diggy. Since releasing his debut mixtape, The First Flight, last November, the praises and accolades have been coming hand over fist.

We recently had the chance to chop it up with the MC/fashion-fiend where he spoke candidly on a handful of topics such: the show’s impact on his music career, the negative comments regarding his older brother JoJo, his feelings towards Lil Twist and Bow Wow, the stigma about “child rappers” and what he personally feels he needs to improve on.

The sudden rise in popularity and hype has to be bittersweet because a lot of comments praise you but downplay your brother. Can you speak on how it feels to receive the success you have right now but have people criticize JoJo at the same time?

First off, I’m super thankful for the response and everybody that supported. I definitely want to shout out everybody who has been rockin’ with me since The First Flight. Concerning JoJo, he’s someone I’ve looked up to rapping my whole life. I don’t have a change in perspective in hearing his skills because he’s been doing it longer than me. He’s older. It’s a different thing to see, but it’s something that I ignore. We really don’t let it [the comments] get to us. He notices it, but we always encourage each other.

To piggyback off that, on the show the viewers actually got to see JoJo and his love for making music. Do you feel that you not showing the world your music aspirations on the show actually helped you in your career?

Maybe to an extent because it’s up in people’s face and when it’s under a big roof it, maybe it makes people see it the wrong way or not want to support. You know what I’m sayin’? The fact that, when it relates to me, people may think, “Why would I even want to buy this kid’s album? We’d just be putting money back into the rich.” Honestly, the way I see it is like, it’s not my money for real.

A lot of people may say, “You’re rich.” And I’m like, “No, I’m not rich. My father’s rich. I’m just living under his roof because I’m a dependent and I’m his son.” But I’m looking at getting my own, that’s why I’m working so hard right now, I want to do it on my own.

Speaking of your family, I know in your latest video, the “Made You Look Freestyle,” you dropped “nigga” a couple of times. How do your parents feel about that?

You know, it’s not the “f-word” or the “s-word,” it’s something that has existed in Hip-Hop. I don’t overuse it or go into overkill. It was in the hook and it may have been in a verse once or twice, but my parents’ reaction towards it isn’t negative at all. It’s a part of Hip-Hop and it doesn’t necessarily have to be something I chose to say in a rhyme. But if it was a curse, they would definitely be disappointed in me. That’s why I don’t curse in my rhymes. I don’t see the “n-word” as a curse at all. That’s just my opinion though.

Let’s shift the topic a little bit. There has “reportedly” been tension between you and Lil’ Twist of Young Money. You want to clear the air on that?

Yeah, man. Twist is like my brother. I love that dude to death. Everything is good with me and Twist. I think the tension was caused because we’re both young rappers and we’re trying to come up at the same time. It’s probably people may see the beef and then want the beef, but there is nothing between me and Twist.

To go back to your “Made You Look” video, you had a line about Bow Wow. I, personally, didn’t see it as a diss. You said something to the extent about his fans not growing with him as he got older, which is true. He’s definitely not as successful as he was earlier in his career. Are you worried about the stigma that “child rappers” get? Or do you feel your music will speak for itself?

I’m happy you brought that up. Nothing against Bow Wow at all. No beef, no diss, no nothing. I was just basically saying the truth. My music isn’t necessarily geared towards only kids. Bow Wow’s was. He actually called me and commended me on my work. He didn’t even mention it, but I’m pretty sure he saw the video. Bow told me I’m doing it real big right now.

I feel that my music is going to grow and I feel my fans are going to grow with me. It’s important that I catch every demographic. I mean age, ethnicity, type of people…everything. That’s why the genres that I listen to and the music that inspires me are pretty wide. The next track that I’m releasing is actually not off a Hip-Hop beat. I’m pretty well rounded when it comes to music and that’s just something that’s always been.

Hip-Hop, like anything else, requires you to practice to get better. You’ve come a long way in a short amount of time and I’m sure you’re constantly working on your craft. That said, what do you feel you need to improve on to take that next step as a rapper?

It’s basically condemning what people think about me before they can even say it. Some people think my uncle helps me, so as soon as they hear it they’re like, “Oh, it’s processed. He probably has major producers on this tape. I wonder how much it cost to do the whole tape.” I think one thing that I have to improve on is NOT addressing it so much. My music is reaching a lot of listeners and I feel like people are becoming aware of it. God willing, people hear this tape and see how I’m doing it on my own.

It takes a lot to look in the mirror and critique yourself.

I’m definitely just a rookie in this game. I try to go back to the roots of Hip-Hop. The Wu-Tangs, the Tribe Called Quests. I listen to them. A lot of younger people have influences from younger artists, which definitely isn’t wrong. I don’t think it’s right either. The come up is everything. I have this book called Fashion: A History from the 18th to the 20th Century and it has every designer from that time frame. I think it’s important for people my age, and even people older, to go back and look at where things came from.

I’m glad you mentioned fashion because you recently tweeted a photo of the prototype of your shoes that are coming out. I know you may not be able to say too much, but do you care to give some insight into that?

Yeah, I can’t say too much, but I got you. That is my sneaker brand, Chivalrous Culture. It should be releasing very, very soon, like around back to school time. It’s a menswear sneaker and definitely a dope shoe. I’m really happy with the way it came out and, of course, I feel it is something a lot of people would wear.

Everyone knows you come from a business minded, entrepreneurial family. What is the best advice they have given you as you as far as your career is concerned? Whether it be your mother, father, brothers or sisters.

The best advice, well, I’ve gotten a lot throughout my life. A lot of it makes sense and it was before the time frame of when I started doing music. Now, a lot of the advice I’ve received can apply to music and life. I think one in particular is from my dad. My dad kicks a lot of knowledge all the time. The one I’m thinking of is pretty basic, but it’s so true. Whenever you are on your high horse, there are always going to be people that are trying to bring you down. He always tells us not to get caught up in it. Regardless of what you are doing, there will always be those people who want to bring you down.

Your mother ever warn you to stay away from people who may not have your best interests at heart?

It’s just something that we know. All of us. We just have to be aware that some people may want to be around us for the wrong reasons. Coming up with my name being what it is and being on a TV that reaches millions over the world, that comes at you from a very young age. As you get older, you find out who’s in and who’s not. It’s something that you just learn. Somewhat like a natural reaction.

That’s true. People will show you themselves if you just wait long enough.

Oh, definitely, definitely. For the most part, I get surrounded by all positive people and people that are here for the right reasons. I’m just thankful I haven’t come across a situation that was really bad and to the point I was fooled by someone.

The First Flight tape dropped in November and we already know what has happened for you since then. What’s next?

The next project is actually coming very soon. I can’t speak on it at all, but I do want people to know that it is coming very soon. I’m pretty sure they’re going to be happy with the end result.

To go back to the whole JoJo topic, have you all considered doing a track together?

Oh most definitely. There have been things that came up and we’d start working on things, but we didn’t finish. But yeah, definitely, it is going to happen.

One last thing before we get out of here. Has Nas contacted you about the “Made You Look” video?

Not yet. But I will tell you this, I’d be very, very happy if he were to hear it. That’s one of my favorite Hip-Hop artists of all time. He’s definitely one of the greatest.

To keep up with Diggy, follow him on Twitter and be sure to check out his blog.