How Diggy Simmons' Musical Hiatus Helped Inspire His Comeback

In 2012, Diggy Simmons seemed poised to be one of the rap game's next great torch-bearers. Having unleashed his debut album Unexpected Arrival after being named a 2011 XXL Freshman, the then-17-year-old had the skills of a certified rap technician and the pedigree of a rap legend. Six years later, Diggy has yet to release a sophomore project. Soon enough, that will change.

Recently, Diggy announced the coming of his as-of-yet-untitled sophomore LP. Its first single, "It Is What it Is," serves as a mission statement for a former child celebrity (and son of the legendary Rev. Run) who's successfully navigated the complications of in-born stardom by ridding himself of unrealistic expectations.

As a former star of the Run's House reality TV series, the rhyme prodigy grew up in front of our eyes à la Kendall or Kylie Jenner. While fame affords exposure and can help set the groundwork for early success, it can also help obscure the things that are most important. For Diggy, who started off his rap career recording his The First Flight mixtape in his bedroom closet nine years ago, his art was most important.

Taking a break from the logistics of plotting hit singles, strategic releases and everything else that accompanies rap stardom, Diggy used his time away from the music scene to re-evaluate his life and jump into other endeavors. During his time off, he's walked the runway for Dolce & Gabbana and jumped into the world of acting. And earlier this year, he landed a recurring role on ABC's Black-ish spinoff Grown-ish.

While fashion and acting are two fields in which he's been thriving, Diggy is now prepping to make his return to his first love. Speaking with XXL, the former Freshman discusses his new LP and his reasons for taking a break from dropping new music.

XXL: Let's talk about your new music. What song is your favorite?

Diggy Simmons: They switch. "It Is What it Is," though. I think that one makes me the happiest.

It feels like that one is your mission statement.

It is. Which is cool because it's the first record we're putting out. It's the mission statement. It feels right.

It's been six years since you dropped your last project? Why such a long wait to drop your next one?

I was really young. I feel like for any artist when they start it's not much to think about. You're not thinking about fans, labels [or] making hits. You're not thinking about any of that extra stuff; you're just thinking about the creative part. So after all of that extra stuff came after the creative part and you're super young, you're like, "Damn, I need that moment to just reel myself back in and find what's important." Find me. Me being a teenager, me being in my 20s, with that intention.

I'm figuring it out—figuring it out in front of people. And I'm an ultra perfectionist to the point where it pisses people around me off. [Laughs]. Like I said, "It Is What it Is." That's what I kinda had to say about myself. I can't be anymore or be any more [than I am]. I can't worry about what people think, 'cause you know, that was a layer of it. Me not living in what I wanted to do.

Not living in my purpose. And as an artist, you're like, "Damn, I wanna be out there. I wanna be competing. I wanna be out here with these guys. I know what I have to offer." So it feels good to come back and feel better—feel good.

Being a perfectionist must have made it hard to record a song called "It Is What it Is."

It's very hard. And I'm practicing it. It's not like it's perfected. Just saying, "You know, it is what it is." And I think there's a lot of people that kinda go through that. Just the overthinking and not just letting life be what it is and letting your best effort be what it is. So it's just kinda like that process of being like, "I just gotta give it everything and just go."

Overthinking things. Analysis paralysis.

Yeah. It hinders growth. And being able to say, "It's okay to bump my head. It's okay if it's not perfect." 'Cause there's perfection in that too. Like, things having quirks. That's also what I'm learning. Like, it's okay. So that's what it's been for me. I'm happy that I could even put that in the music. This means a lot to me, being able to finish the project. From not having music out for so long. Like, "Damn...it's here." I was able to reel myself in and just do it.

How did you reel yourself in? How did you put yourself in a position to make this project?

I just had to let my process and how I went about things be sort of like isolated from any insecurities, any fears, anything. Because, like, a layer that comes with it too—with any artist—is kinda like the perception of yourself and what are people gonna think. So it's like, I have to make the album that I wanna make and just do it.

I think it came with not doing it for so long. I'm tired of feeling like I'm not living in my purpose and being creative. Doing what I do, going on tour and going on stage and being Diggy. That's who I wanna be, that's what I wanna do. So it's a good feeling.

Right, you came into the game being naturally over-exposed. Being a Freshman, being on a reality TV show...

Yeah, that's the thing. It kinda all just happened. I'm thankful for the process of what happened, because that's my story. I did some of the coolest shit that you could do at that age. So yeah, like you said, Freshman and TV show and music. Basically a freestyle is what made everything kinda go crazy. You learn how to deal with things. That's a part of the experience as well. You learn how to deal with attention. You learn how to deal with people.

Don't want to say your success happened overnight, but...

It happened fast. Trust me, it happened fast.

Did you feel like your success came too easily at first?

No, not at all. I was like, "Oh, the thing I set out to do is happening." I didn't know how long it would take—I don't even think I was thinking about that. I think I was really enjoying making the music I made because it was me. I come from looking at Kanye and Pharrell and Lupe—that kind of lyricist-backpacker. So I was just happy I was making the music I want to make and I was being me. Especially being on Run's House, where it's your family and everyone's looking at you as maybe just a kid in the family. I was happy to be an individual. Getting the creative part out. And then it blew up.

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