Getting Real—And Vulnerable—With Diggy Simmons

When I first met Diggy Simmons, I extended my hand to introduce myself; Diggy ignored it and brought me in for a hug, which turned out to be the perfect indication of the type of guy he is. For our interview, we walked around SoHo; I brought my disposable camera, freshly purchased from Rite Aid, and he grabbed his skateboard from the trunk of his Porsche. It was work, but it felt more like fun than anything else. This is pretty standard for Diggy.

For Diggy, all of his work is an extension of his passions, and so it’s rare that he’s not enjoying himself. As the son of Joseph Simmons, a founding member of iconic hip-hop group Run-DMC, Diggy was naturally drawn to music. But then there’s also his love of acting, humanitarian work, fashion, and even a really intense affinity for memes. He's disarmingly normal for coming from rap royalty—and he's also emotionally open, and vulnerable as hell.

“My thing is me being vulnerable,” Diggy told me. “I’m not all the way there. I haven’t figured out how to do all the things I want to do consistently, but I’m working toward it.”

This emotional honesty is on display in his new single, “It Is What It Is,” which precedes his forthcoming album—the first piece of work he’s released in six years. It's centered around the concept of vulnerability and of figuring yourself out. 

“We have to find the balance of being open while we figure it out,” he said. “It’s not an easy balance. I’m in the middle of doing that.”

And yet, Diggy makes it sound really easy—in fact, he makes lots of things seem easy. Case in point: He put together his soon-to-be-released album in the span of just a few months.

I asked him how that was even possible. “How did I get this [album] done? I think I just had to give myself more of a chance… Whether you feel low or whether you feel like you can’t accomplish the things you want to or if you have anything holding you back, you have to give yourself that chance to try.”

Diggy's sincerity is striking, but it's important to him that his fans know how empowering it is to believe in yourself and fight through the self-doubt. He said, “It feels really good to talk about what I’ve been through... I see it all the time on Twitter. People saying: 'I’m going through this.' Or: 'I don’t feel too good.' I wanna tell people: Me too.”

Diggy doesn't have much faith in social media as a means of communication, and thinks it's detrimental to the young people who are on it all the time.

“Everybody’s looking at what everybody else has," he said to me, leaning forward on the couch and ignoring his phone as it unceremoniously chimed with a notification. “You can just swipe and you have too much access to what everyone’s doing… I feel like what makes a lot of people go crazy is that it stunts people’s growth. That’s something even I can fall into… thinking too much about what people think about me.”

“But then again,” he said, more to himself than to me. “[Without it], I wouldn’t have good memes. I mean, when I think of the pros and cons, I’m always like: but memes.”

Beyond memes and music, Diggy has a multitude of other creative outlets. He’s been a crowd favorite character on Grown-ish. He worked on a short film when he first moved to New York after completing his album. He’s involved with his family’s charity, Art For Life, as well as for The Boys and Girls Club of America. He hasn’t gone to college, but, he told me, if he had the chance, he’d major in African American studies. And so I ask him: “Can you tell me about being a black man in America?”

He looked at me and said, “Sure.” But then he paused: “Um, what part?”

We both laughed. “Sorry,” I said. “How about you just tell me what it’s like being a black man in the music industry.”

He nodded and began speaking immediately: “I think it's a continuous fight, for equality and to be seen as an individual. And not to be marginalized as just a black man doing music.” He looked momentarily frustrated before he finished his thought, “[Not] making everyone seem the same or as having the same intentions, having the same messages.”

So that’s what he’s working on: dismantling the antiquated idea that all black people in the industry are the same. Diggy’s approaching it from a place of honest self-reflection and vulnerable truth-telling. It’s refreshing—he’s refreshing. Diggy creates for the love of creation, and that sentiment alone is a breath of fresh air.