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Your Weekend Playlist, Courtesy of Diggy Simmons

On one of the balmiest days NYC has seen this summer, I met up with Diggy Simmons at the Standard Hotel in the heart of the Meatpacking District. He’s a little bit late due to car troubles (he drives a vintage), but in a hop, skip, and a hasty Uber ride over, he finally arrives — sincere apologies in tow.

Despite the fact that he’s late, it’s hot, and we’re sitting in an unfamiliar hotel room, Simmons knows how to put everyone at ease. He sits down on the couch, cracking jokes nonchalantly as ever, and I can’t help but feel struck by his commanding yet welcoming presence. He’s cool, calm, and confident, and although neither of us have stayed at the Standard before, he makes it feel as if I’m chatting with him in the comfort of his own home.

As I shake his hand, I notice a large band-aid covering a spot by his elbow.

“I was skateboarding in Chinatown, and I saw a fan wave,” Simmons recalls, “I went to say hello, but fell and totally ate shit.”

He laughs sheepishly, then pauses. “Don’t put that in.” I nod and make a mental note.

But then he laughs again, giving me the green light. “Actually, you know what, go ahead.”

This is Diggy Simmons, the rising hip-hop artist who is poised to take the music scene by storm. It might sound cliche to say that Simmons was “born to make music,” but in his case, it could not be any more literal. As the son of none other than Run-DMC’s founding member, Joseph Simmons, a deep-rooted and incredibly influential hip-hop legacy courses through Simmons’ veins. Over the last few years, Simmons has taken a break from music, an industry in which he’d begun to find solid footing as an artist separate from his father. Despite his respite from the studio, make no mistake — featured by Billboard as an “Artist to Watch” along with earning a spot on XXL’s annual Freshmen list in 2011, Simmons’ musical reputation is one with the accolades to match.

Fresh off the completion of a full-length studio album, we had the opportunity to talk with Simmons about what he’s been up to since his last release in 2015. From his role in hit TV show, Grown-ish, to the ways in which his sound has changed and evolved, read on to get a glimpse into life and times of Diggy Simmons.

Additionally, Simmons has curated a weekend playlist featuring some of his favorite songs of the moment. Be sure to give it a listen, and get a peek into the creative headspace he inhabits whether he’s in the studio, working on set, or just chilling.

How would you describe yourself as an artist? 

I don’t want to come off vain, but I’m very honest. Vulnerable. I don’t hold much back, because the way I started making music was from a very therapeutic place. Being able to have experiences and go through things, good or bad, it feels really cool to be able to put that in song form and have it actually sound good. It’s an honest approach.

Do you think of yourself first and foremost as a musician? I know you have some other creative endeavors you’re doing.

Music is my first love, so to speak. Everything else kind of came after I did music. Everything I do, I am passionate about. Whether it’s projects I work on in film and television, or anything in fashion or style. Music is first, but anything I do, I’m passionate about.

I know that you make mostly hip-hop music. Can you talk to me about how your outlook on hip-hop has changed now that you’re making music yourself? Your familial legacy when it comes to the hip-hop music scene is quite renowned, so what is it like for you to go from that background to actually making it on your own? 

I feel like a lot of my inspiration and artists that I’m into have always played a very pivotal role in me wanting to make music. Music has always been the background. Being younger, and being inspired by Pharrell, or Kanye, or Lupe, these kinds of guys that have brought a new aesthetic to hip-hop. That’s kind of who I grew up looking up to. They’re a huge inspiration behind who I am as an artist, and how I’ve evolved.

Would you say those artists have shaped your sound? How would you describe your sound?

Lyrically, it comes from a vulnerable place. Sonically, it’s complicated — I grew up listening to hip-hop of course, but the rides to church were Anita Baker and Sade. Melody and melodic sounding production, live instrumentation, is something that has always played a part in my sound. As much as I am a 90s-head when it comes to hip-hop, I also have an appreciation for adding more melodic sounds and having a balance.

Perhaps bringing a softer side to hip-hop?

Yeah. I’d say from a sonic standpoint. The production might sound that way, but the way in which I end up rapping is just aggressive. I grew up seeing the way that my dad raps, and those artists from ’80s to ’90s period were all just super boastful. It was just that sort of energy. I’m like a rapper’s rapper.

Can you talk a little about your latest projects you’ve been working on? What have you been up to recently? I know you’ve been doing some stuff in television, what was working on “Grown-ish” like?

Yeah! “Grown-ish” was really awesome. The reaction from the show was incredible, the messages, what people have taken from the episodes is really amazing. I feel like it’s good for young people to have — we talk about it a lot on social media, but I love how open people are. The amount of information being passed back and forth is insane. I think it’s cool that you can see that open-mindedness on television too. It feels good to be a part of something like that, something that encourages people to have thought-provoking conversations about our society.

Have you been in the studio making music recently?

D: Yes! We started the album in LA in January, and we finished in May. We caught a tempo, we had a mission. I knew what I wanted to say, it’s been years since I dropped a project so obviously I have all these things I want to say, and all these things I’ve experienced over 23 years. It’s that age where everyone is figuring it out, and we’re trying to figure out what works for us. Who we are, and what we’re doing. Who works best for us in our lives, and the types of people we want to be around. I just had those ideas, and I’m back in the studio now. I have the production set out, and let’s just do it. And we did it. We didn’t overthink it, I’m really proud of it.

Do you know when you’re going to release it? 

Fall. Fall of 2018. It’s so crazy, it all came together in a year. That’s kind of rare. It’s exciting.

I feel like it’ll also be a cool thing to look back on in the future. To me, 23 is the age where you’re at the cusp of true adulthood. You’ll always be able to look back and remember the project you made and released, all in the span of that year.

Yeah! It feels crazy to even sit here speaking with you about it. It’s that process of making an album or a project has always taken so much longer. Usually, I feel removed from the creative process by the time I talk about my work. I’m in group chats, with my executive producer, and we bounce ideas back and forth.

Is there a message or overarching theme in this upcoming album that your fans should listen or look out for? 

Overcoming. A lot of the reason why I took a break is because I spent a lot of time overthinking things. I feel like a lot of people in our generation kind of have that element of hesitation as we’re trying to figure things out. We live in the era of social media where we’re looking at everything that other people are doing, so that’s a distraction from making us feel like we’re progressing and doing what we’re supposed to be doing. The theme is just overcoming all of that. Not caring too much about what you don’t have control over. These are the cards I’ve been dealt, but life goes on so I have to move forward, with whatever it is that’s in front of me. It’s just me being introspective.

Special thanks to The Standard Highline.

Stay tuned to Milk for more interviews and weekend playlists from artists we love. 

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