Diggy Simmons Interview: On Pressing the Reset Button on His Rap Career - DJBooth

Diggy Simmons Presses the Reset Button on His Rap Career

“I think overcoming the idea of perfection would help a lot of people sleep better at night.”
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Diggy Simmons Interview, 2018

Rappers are much like sunsets: compelling, noteworthy, and there and gone before we get the chance to appreciate them. There are plenty of reasons why artists fall out of frame, but for hip-hop royal Diggy Simmons, now 23 and making his hip-hop comeback, his hiatus was caused by a rabid need for perfection.

“This is something that I’ve always wanted to do, but it was more so a timing thing on my part,” Diggy tells me over the phone. “Being ready, not overthinking the creative process anymore… That was a big reason why I couldn’t get it done because I was in my head overthinking: ‘What should it be? Is this good enough?’ I finally just said I have to let go if I want to see the growth that I wanna see not just with my career, but with my own life.”

Simmons’ trajectory starts strong: securing a 2011 XXL Freshman spot and following up with a debut album in 2012. From there, though, his career becomes a bit spotty and devolves into a peppering of loosies and videos, and Yo Gotti features. Before we know it, 2015 comes and goes, as does Diggy’s musical output.

But Diggy Simmons himself did not leave the spotlight. While not making music, Simmons has a hand in acting and fashion, both of which have helped him overcome his desire to be perfect. “I’ve learned to say it’s okay if it’s not perfect-perfect because that took me away for so long,” he admits. “It’s cool if it’s flawed, that’s awesome, too. That’s real, too.”

Now, Simmons is ready to enter into the next phase of his rap career with a new single dropping August 3 and a new album coming shortly thereafter. He is done overthinking, and that freedom has given Diggy the creative energy necessary to craft his own, rich sound. “For this album, something that we always said from the beginning was ‘rich sounds,’” Simmons explains. “When you hear the album, there’s so many rich sounds on it. The quality of the production… We had live instrumentation and we did great things with the post-production. Lyrically, the messages that we got across were rich, too, just rich in quality.”

On the heels of his next chapter, Diggy Simmons already knows what he wants his legacy to be: “I’d want people to say that I helped them.” As long as that sincerity permeates through the music, Diggy’s projections will be on the money.

DJBooth’s full interview with Diggy Simmons, lightly edited for content and clarity, follows below.

Diggy Simmons Interview, 2018

DJBooth: I wanted to start by asking you: What’s one question you wish you were asked more often?

Diggy: Oh, wow. That’s a good one, I wish I got to think about this one more. Maybe…

What’s one question you get asked too often?

Questions about my family and pressure. “Is there any pressure?” I get asked that a lot.

Do you have a go-to for that?

Yeah! I’ve had the answer to that question kind of down pat, almost like a robot, for years now.

I bet it gets frustrating.

I understand the question and where it comes from, but it’s definitely asked a lot.

In 2011 you’re a XXL Freshman, 2012 we’ve got the project, in 2015 you’re doing tracks with Yo Gotti, and now in 2018, you’re back with a new single and hopefully more on the way. How does it feel to be dropping new music?

I don’t really think about everything that surrounds it, if you understand what I’m saying. It feels good to me. It’s such a good feeling to be making music again and putting my point of view out there. Just being introspective about life just feels really good, you know?

Was there one moment that prompted your return?

You know, this is something that I’ve always wanted to do, but it was more so a timing thing on my part. Being ready, not overthinking the creative process anymore… That was a big reason why I couldn’t get it done because I was in my head overthinking: “What should it be? Is this good enough?” I finally just said I have to let go if I want to see the growth that I wanna see not just with my career, but with my own life. I feel like I’m growing by finally taking off those mental shackles and just doing something.

How do you train yourself to get out of your head?

I definitely don’t have it down pat, I’ll say that for sure [laughs]. I didn’t conquer it, but I feel like I’m getting closer, with the fact that I [have new music]. A lot of time, it has to do with zoning out of social media or thinking too much about what is the perception of you and allowing yourself to be free. Separating yourself from things that are distractions or don’t allow you to be your best self.

It’s very admirable that you’re coming into hip-hop with a sound that’s decidedly not on trend. You could’ve just thrown out a trap hit, why didn’t you?

That’s not really my style. I enjoy trap music so much; I enjoy lots of different music. It’s just about staying true to myself and wanting to push myself sonically and give the world something a bit different, sonically, for hip-hop. I always like pushing things.

How indicative is your new single, “It Is What It Is,” of your new direction?

As you hear the full project, you’ll definitely come to kinda see that the whole sound of it takes on after that vibe. No drums on that song, but there will be drums on the album.

Who were you listening to during your hiatus?

That’s six years! I’m always listening to Sade, that’s just my whole life. AZ, a lot of AZ over the past two years. Camp Lo is a favorite of mine; I like John Mayer a lot. My taste and style is so all over the place, and that pushes the sound forward of what I do because I get influences from so many different places.

Any unexpected influences?

Jeez, I think John Mayer could be one. I like the Arctic Monkeys, MGMT. I like alternative stuff, I like rock stuff…

With all of these influences, how would you define hip-hop in 2018?

Just subgenres, that word. Hip-hop’s not one thing, it’s not one sound. There’s so many different people from so many different places that have had so many different experiences, and they make hip-hop music. Obviously, hip-hop’s not very old. So now I feel like we’re starting to see different branches on this tree and it’s getting bigger, and it’s cool to see these different people’s takes on hip-hop.

How would you define your own hip-hop identity?

I wanna give it a word or a genre. For this album, something that we always said from the beginning was “rich sounds.” When you hear the album, there’s so many rich sounds on it. The quality of the production… We had live instrumentation and we did great things with the post-production. Lyrically, the messages that we got across were rich, too, just rich in quality.

How instrumental have your exterior endeavors in acting and fashion been to you finding your “rich sound?”

I feel like with everything that I do… It just makes me feel good because I just like things to be together. That just goes for my style in clothing and all the endeavors I take on, I wanna do everything at a really high taste level and that’s what feels good to me. With that, I’ve learned to say it’s okay if it’s not perfect-perfect because that took me away for so long. It’s cool if it’s flawed, that’s awesome, too. That’s real, too.

Do you think perfection is possible, or do we have to overcome it?

I think overcoming the idea of perfection would help a lot of people sleep better at night. The idea of it definitely drives me crazy, drives a lot of people crazy, especially in this world of social media. We live in a whole other universe [there] that isn’t life. I think we definitely have to overcome that, and that’s something that we explore on the album a lot.

If it were in your control, 10 years from now, what would you want people to say about the Diggy legacy?

I’d want people to be inspired and take away from it all of the themes and experiences that I went through, and I’d want people to say that I helped them. Hopefully, the things that I needed help through, that I put in the music, and the things that I’ve had struggles with can help people get through theirs. That’s really it, honestly.

So, what’s one question you wish you were asked more often?

Oh! More often… I wouldn’t say just interviewers, but I guess just more conversations about how people are feeling. Not just for me, but in general. Just sitting down and talking to people one-on-one about what’s really going on with each other could help people more.

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