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Skyzoo is a wordsmith. Talking to him is like talking to a cool, young English professor who could school you in rhymes as well as hyperboles. If he weren’t rapping he said he’d probably be taking my job, working as a journalist for some magazine. Dude mastered the English language in the early ’90s as a nine-year-old on the 18th floor of a high rise in Brooklyn’s Crown Heights, and “I break the microphone, and I break it in pieces, and I break the microphone in half,” was probably his first flow.

His critically acclaimed debut LP The Salvation was released in 2009 to reviews immediately calling it a hip-hop classic. In subsequent years, he’s been dropping mixtapes from New York on an independent label called Duck Down Records, working with artists like Wale, Lloyd Banks and Talib Kweli.  He’s been co-signed by the likes of Spike Lee, and he got a taste of A-list New York City life when he dated New York Yankees star player Derek Jeter’s sister for four years.

Skyzoo has been in the game quietly making noise for over 10 years – since Freestyle Friday on BET’s 106 & Park was making rap careers happen. But in a culture where designer label name-dropping and hashtag rap see greater results than storytellers and artists who are truer to the original essence of hip-hop, Skyzoo is still an underdog on the come up trying to reach a level of Jay-Z-like success.

After recently doing shows in South Africa and Europe, we got a chance to catch up with Sky just before he touches Australian soil for the first time. The Australian leg of the Dream Deferred Tour hits Melbourne and Sydney this weekend (24 May and 25 May, respectively). So, we figured we’d get into the head beneath the Yankees cap before we catch him live.

I hear you always write songs starting with the title. How does that help you write a dope song?

It tells me what to write about. I’ll be walking down the street and a bus goes by and there’s an ad that says something and I flip it. Perfect example, I have a record called First Generation Rich (FGR for short), which has kind of taken on a life of its own. Now, I have FGR hats because “first generation rich” really started picking up steam as a phrase and a slogan.  The way that came about was from watching an interview with Oprah Winfrey and Dwyane Wade. It was a term they brought up in the conversation: being first generation rich, being the first person in your family to make it, do something and have money. I literally watched the interview, and when they said it I was like “Oh, shit. There it is.” It’s weird but it works.

You’ve got a song called Spike Lee Was My Hero. Then, he makes an appearance in the video. How was it to actually meet your hero?

It was amazing. It was spoken into existence. I did the record and three weeks later my hero was tweeting me like, “Yo, I’m honored. Whatever you want to do, let’s do it.” Now Spike emails all the time. I hit him up on Twitter. And it’s like, “Dang I made my hero my homie.” It’s an honor, and I don’t take it lightly. His son heard the song and played it for him. Next thing he’s tweeting me and quoting lines on Twitter. The coolest thing about being in the game so long is the people you grew up on become the names in your phone.

If you weren’t rapping, what do you think you would be doing?

Probably something still in the arts or some sort of writing. Either journalist or EIC [editor in chief] of some newspaper or magazine. Maybe some type of English professor or teacher in school.

Are you still writing a book?

I’m working on that now. Hopefully, I’ll have it out by the end of the year. It’s a lyric book. It breaks down a bunch of my songs, the meanings behind them and the inspiration behind a lot of the things I say. A lot of people listen to my music and say it’s frisbees – it’s over ya head and you have to listen to it a lot to break it down and get it. So, this is a how-to guide. I might just publish it myself, let it bubble and then let [publishers] holla.

Do you ever feel pressure to dumb down and be less of a lyrical rapper?

If anything, I only feel pressure from myself to continue to be dope. I put more pressure on myself than anybody puts on me. As far as dumbing down and things like that. Yeah, you think about it because you think about the business aspect. You think about where you want to go in your career. And you think about the audience. But I know that the audience that I have, which is so varied and so different, love what I do, and they rock with me because I get busy. I don’t hold no punches. I get busy when it comes to the rhymes and the storytelling. To me, it’s just about balance. That’s with anything in life. If you’ve got balance, your life will be all right.

Did you really date Derek Jeter’s sister?

Yeah. Four years.

How’d you meet?

She was actually at one of my shows with Derek and Vanessa Manillo, Nick Lachey’s wife now. They all came to the show. I met Derek and Vanessa then met his sister, and we kept in touch from there, started dating and we actually were engaged. Derek was calling me his little brother. We would go around to restaurants or Yankee games. We went on vacation – me, Derek, her and a bunch of other athletes – and were hanging out with Michael Jordan taking pictures and smoking cigars. That didn’t even happen just once. Jordan’s the homie. I did it all. Then, we split. Things fall apart.

Why’d you choose the title A Dream Deferred for the new album?

A Dream Deferred was one of those poems we had to learn in the seventh grade, and it always stuck to me. It’s simple, but it hit hard. What happens to a dream deferred? What happens when you have these dreams of where you were gonna go, and none of it goes the way you predicted, hoped or imagined. What are you gonna do? Your dream is deferred. Now what? When I was writing the album, I was thinking about the things I was going through and where I was at in life, and it made the most sense to call it that.

How does this album differ from The Salvation?

I relate it to basketball. You can still get better with your jumper every day. People were calling The Salvation a classic off top, but I’m always going to continue to grow and expand from a lyrical and musical standpoint. No matter how many rings Jordan won, the day after the championship, he was in the gym shooting. That’s how I look at it. If I won a ring off The Salvation, I was still in the gym the next day shooting. The experiences on A Dream Deferred only took place in three years, but the difference is the maturity. I’m getting better as an MC regardless of how dope I am.

Every album is about new experiences, new things that go on in life as well as new sounds. Each album is going to sound different from the previous, and that’s the goal. I don’t think anybody should make an album that sounds like the last one because, if that’s the case, why make the new one?

Over the last 10 years, it seemed like New York wasn’t really running the rap game how it used to. But lately it seems like there’s a lot of talent coming out of there? Do you think you guys are coming back?

I still think we’re not running it at all. I still think we kind of disappeared. You have your A$APs and French Montanas. Maino’s been a staple on the radio, too. So we do have our artists waving the flag and continuing to represent us, but there’s not enough. Those are dope artists, and they’re doing incredibly well as far as making it pop. But it’s not like it was where we’re running it – but not even running it – where there’s a significant amount of us who are getting that shot. There are a lot of artists with talent who would have probably had a deal a year ago if they weren’t from New York. Labels are literally [passing up people because they’re from New York], but if they were from Chicago or L.A., their door would be getting kicked in.

You had a good run on 106 & Park’s Freestyle Friday back in the day, is that where you first started getting recognition?

I definitely got some notoriety, but the game was different back then. Yes, labels would drop everything at 6:45 and turn to BET to watch Freestyle Friday. But there weren’t blogs and Instagram and Twitter where you can really capitalise off of the moment. The only way to capitalise was getting a deal. You couldn’t be on Freestyle Friday then drop a mixtape to all the blogs the next day. People couldn’t follow you. The only way they could follow you was if they ran into you at the sneaker spot on the street or something. I always credit my notoriety to Cloud 9 with 9th Wonder after ‘06. He was giving me beats and telling people on the streets and in interviews “Sky is nice. Yeah, Sky. He get busy.” That’s when things really started getting crazy.

What’s your favorite song you’ve recorded so far?

Probably Langston’s Pen from an album I did called Live From The Tape Deck with Illmind. Because if someone said, “Who is Skyzoo? Where is he from? What is he about?” that would be the record you would play – kind of like a movie trailer for a movie. If you’ve got a film, and you need to get this two-minute trailer out to promote it, mine would be Langston’s Pen. It does a great job of saying what I’m about and what I stand tall for.

Skyzoo Australian tour May 2013
Fri May 24th @ The Laundry, Melbourne
Sat May 25th @ Oxford Art Factory (The Gallery Room), Sydney