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Diggy Simmons — A Day in the Life

Diana Levine for AOL

“Life as a shorty shouldn’t be so rough,” Inspectah Deck raps on Wu-Tang Clan‘s 1993 hit “C.R.E.A.M.” Diggy Simmons, 17, didn’t face the same harsh realities of growing up “on the crime side” like the hip-hop veteran but the youthful rapper still experiences struggle and has a story to tell. Rap is based off that foundation, and as the genre evolves so does the definition of what constitutes a struggle.

For the New York native, who’s eagerly spreading the word about his debut album, Unexpected Arrival, which The BoomBox was witness to on March 19, his difficulty lies in being confronted with naysayers and skeptics challenging his lyrical abilities all because he grew up with a famous father, Rev. Run of Run-DMC, and lives an affluent lifestyle.

“The reason why people dismiss me is because everybody wants to hear about that story that started at the very bottom, nothing at all, and made it to the top,” Diggy tells The BoomBox. “My situation and where people may not see it, but will with the album, is that everybody has a story. As great as everybody else is, I’m a young dude and people may have not believed in me, but I surpassed everything that everybody was saying. Make your arrival in life special, no matter who says what.”

The day before his album officially released on March 20, he makes his arrival on time at New York City’s Hot 97 radio station, freshly dressed in a black Neil Barrett jacket and matching sneakers. At 10AM, the teen sits down with Cipha Sounds, Peter Rosenberg and Kay Foxx of The Cipha Sounds and Rosenberg show, as they get into his mind and try their best to get the entertainer to divulge juicy gossip.

Kay Foxx compared him to a “young Kanye West” and tried to see if he’d falter when asked if his brother Jo Jo, who was once trying his own hand at a rap career, supported Unexpected Arrival. “He liked it,” Diggy replies. Ever the comedian, Cipha touched on his “hatred” for the rapper’s “silver spoon” upbringing. “My motive was to never follow in my dad’s footsteps,” Diggy states. Before heading out to his pre-taped performance at BET’s “106 & Park,” Peter Rosenberg gave the “Two Up” creator a wealth of praise for crafting a solid album and Diggy recorded some drops for a radio promo. “I don’t think I can say this — the b-i-… word,” he explains of the expletive. “I don’t use that language.”

An hour later, Diggy is welcomed to CBS studios in midtown Manhattan — where BET headquarters sits — by a sea of screaming girls, who have lined up outside the building for a taping of “106 & Park.” Graciously waving, he throws a smile in their direction and enters the building to meet with hosts Rosci and Terrence J. Hearts were melted on that pavement.


Watch A Day in the Life of Diggy Simmons

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Videography by Elizabeth Bruneau & Diana Levine, Production by Elizabeth Bruneau

Inside a spacious dressing room, Diggy is greeted by his friend and DJ Spin King. There’s no time to play around here; there’s a show to do and Diggy’s steering the operation. Guidelines on how he and his record-spinning co-pilot will interact onstage for the “106 & Park” crowd are discussed, a soundcheck follows and a wardrobe change is executed before he grabs the mic.

“He’s very [critical] of his work,” Spin King shares of Diggy’s career practices. “Not saying he’s never satisfied, but he makes sure that everything is the way he wants it to be. He’ll practice over and over. We went from rehearsal from 1PM to 11PM [yesterday]. Straight rehearsal. He really puts his heart and effort for his Jetsetters.”

Tracks from Unexpected Arrival are what Diggy rhymes through at “106 & Park,” as he hits “Tom Edison,” “88,” “Two Up,” “Do It Like You” featuring an assist from crooner Jeremih and “4 Letter Word,” among others. His spirit never breaks — though he sweats a bit in his designer snakeskin-decorated jacket — his momentum is strong and the audience is engaged. For a 17-year-old who left school in the 9th grade to be taught at home by his former nanny — she has a teaching degree — this is a byproduct of determination and a dream fulfilled.

One of the songs he performs, which he wrote and both raps and sings on — much like his biggest hip-hop influence Kanye West — is a personal favorite for him. “I wouldn’t say I’m afraid to do things,” admits Diggy, who’s also a fan of bands Arctic Monkeys and Passion Pit. “I just always want things to sound like I envision them. So sometimes I’ll hold back. That’s something during the process I’ve gotten out of. When I was doing ’4 Letter Word,’ I was like, timid, singing and stuff. [The people in the studio] were like, ‘Yo, you sound so good. What’s your problem? Get in the booth!’ ‘Cause i was doing melodies for a singer to do. I like to write my hooks too even if a singer’s gonna be on it. They were like, ‘You do that.’ I got in the booth and it sounded great. Before I hit puberty I could sing too. But once I hit that stage I was like ‘I ain’t messing with it.’ This song is amazing.”

After chopping it up with Rosci and Terrence J, Diggy heads to Highline Ballroom for another soundcheck. Yes, the young Simmons is putting on two shows in one day — this concert will be an exclusive showcase of his Unexpected Arrival material with some added gems. Girls and their parents have been lined up since 8:30AM — it’s now 4:30PM — to hold a spot so once the doors open, they can stand firm at the front of the stage. Diggy takes time out to sign copies of his album for fans and a young lady even gives him a heart-shaped balloon with her name on it.

See Photos of Diggy Simmon’s Day in the Life
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During some downtime, the gifted lyricist addresses a topic his Jetsetters have been inquiring about: Is he dissing singer Bobby Brown on Unexpected Arrival? “I’m a fan,” he admits with a smile. “On ‘The Reign’ I say, ‘Can you stand the reign? New Edition-post Bobby,’ which means I was playing off the fact that the song is called ‘The Reign’ and it’s gonna be a long time before I touch the ground. That’s what I was talking about in that song. On ’88′ was a reference: ‘I’m only two years in and a couple of months/ Yeah, the road was Bobby Brown, it had a couple of bumps.’ I wasn’t referring to Bobby Brown’s life. More so, something that people from the ’80s would know what I’m talking about. I was talking about how my life is bumpy. Something that Bobby Brown was about.”

Soundcheck is done at Highline, a return trip to BET “106 & Park” is made for a live surprise visit around 6PM and along the way, while driving in a turtle-top van, Diggy witnesses an interracial couple canoodling on a New York City street corner. “Look at that couple!” he exclaims. “That’s sweet.” Inquiring minds and his female Jetsetters are surely eager to know if Diggy has a girlfriend, and from his reaction to the PDA on the sidewalk, he’s in search of the perfect one to be by his side.

“A girl that can be herself around me,” the rhymer says of what he looks for in a partner. “I don’t want her to put on a front for me. I want to know all of her. I want to be able to do the same thing with her. Its about compatibility and feeling like we’re best friends before anything.”

Back at Highline Ballroom, his show — hosted by Hot 97′s Angie Martinez — gets underway. He takes the stage at 8:30PM to booming applause, girls thrusting posters decorated with his face in the air and the support of his family — dad Rev. Run, mom, grandparents, siblings and more are in the audience. Diggy moves through songs like “Special Occasion,” “Copy, Paste,” “4 Letter Word,” “88″ and “Two Up” for the packed crowd, throwing out “I love you” to his Jetsetters when the moment arrives. A look into the endearing faces of his fans proves the feeling is reciprocated.

With a debut LP out for mass consumption, there’s already talk of what’s next for the rap upstart. New ventures will come organically. Right now, Diggy Simmons is focused on his hip-hop responsibility.

“I’m really proud of my album,” he shares. “I hope I can get Best Hip-Hop Album at the Grammys or even Best Album. I hope I can get Best everything at every awards show. God-willing I can break boundaries for hip-hop. That’s one of my biggest things — besides wanting people to aspire to be what they want to be and get out of that thing that they can’t do something just ’cause people may not believe in them. Besides that fact, I want people to know that their talent starts inside of them, before people believe in them. My biggest thing is to do that for hip-hop.”

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