Quietly, Skyzoo has assembled a near faultless catalog of quality Hip Hop releases. Critically acclaimed projects like his 2006 collaborative album with 9th Wonder, Cloud 9: The 3 Day High, or 2007’s “Corner Store Classic” mixtape, or The Salvation in 2009, or Live From The Tape Deck (with !llmind) all brim with lyrical ingenuity and contextual freshness. After eight years-plus, he sounds more fierce with each release, more focused with each bar—as if his life away from the mic only exists to fuel his craft. In any other era in Hip Hop history, Brooklyn’s Gregory Skyler Taylor could be a household name.

But in the Indie Era the field is crowded and the rules are opaque. Success is somehow both pervasive and elusive. A respectable Klout score isn’t the same as a respectable credit score. It’s the odd dichotomy of the modern independent grind. Between anecdotes on his go-to producer, !llmind, Kid ‘n Play, Demos and how Diddy deserves the credit for removing some of the sting from what it means to “crossover”—Skyzoo tangibly puts his career into perspective.

“I haven’t worked a real job in almost seven years,” he told HipHopDX in the greenroom of Manhattan’s S.O.B.’s nightclub following Celebrity B.L.A.P. producer showcase (February 11). “I’m definitely blessed to say that I wake up in the morning and just make music for a living, travel the world, get free clothes, get free gear, get paid to see the world, get paid to travel and take pictures in front of different monuments, different cities, and have fans.”

Skyzoo Explains His Chemistry With !llmind & Crossing Over

HipHopDX: I know it can be difficult being an independent artist—especially a talented independent artist—and with all the revenue streams and the way it works, it’s not just selling records anymore.

Skyzoo: Oh no, not at all. You get it. You definitely get how it goes.

DX: Second thing I want to say is thank you. I always talk about my first interview being 9th Wonder and Jean Grae at the Jeanius listening party at Fat Beats in 2009. Before I got the chance to talk to them, you were the first person I interviewed [that night]. I asked you about 9th Wonder. You described him as “your [DJ Toomp].” T.I. was working extensively with DJ Toomp then. 9th Wonder was your Toomp at that point in 2009. Who’s your Toomp now?

Skyzoo: This guy playing right here, !llmind. Hands down. I think, with !llmind—besides the fact that he lives up the block from me—literally, the same wavelength of wanting to be everything we were but become everything we can be within the music. As far as the growth; as far as the expansion; as far as being able to make the sound as big as it can become without losing the core and root. A lot of people try to expand and grow, but they lose what started them, or who their core or fan base is. Or some people just stay stagnant. They stay in a box, and they don’t really grow. Why can’t you do both?

I grew up in an era where you did both. You had your core and then you grew, and they grew with you. You grab more people along the way, and the line of people behind you just got bigger. I grew up on that side whether you’re talking about [The Notorious B.I.G], Jay-Z, Eminem, Nas or Andre 3000. I grew up in that era. So why can’t it still be like that? Not saying be old school, but just the same idea and same theory of taking what you have and making it bigger without losing where you came from. With that being said, !llmind, he gets it as far as keeping it rooted but trying to make it as big as it can be, and expanding, grow, and crossover without losing anything.

When people hear the word “crossover,” whether it’s underground or just deeply rooted Hip Hop artists, they get scared. Like, “Crossover? We’re about to lose them.” Why can’t you do that while remaining who you are and keeping y’all but getting more people to notice it? What it really means is getting more people to be on y’all side and agree with y’all being the fans. My Toomp is definitely !llmind at this point. That’s not to take away from 9th at all, it’s just where I want to go musically—the sound—and how I see it, he gets it before I even say it.

DX: Is that really the case anymore? Does crossover still have a negative connotation to it [as it did] when EPMD dropped the joint [“Crossover”]?

Skyzoo: It’s totally different from that, but I think people—from a fan’s perspective—people still look at it from a certain way. Back then, the artists looked at it a certain way like you read all these stories. I remember reading these stories about Kid ‘n’ Play, MC Hammer and all these guys would have people getting on them. Artists would get on them for doing movies, cartoons, and doing toys. Kid ‘n’ Play would say, “Yo, we were the first ones doing the comic books, the cartoons. We almost had a toy before the deal fell through.” I remember reading all that, and how so many artists were against them. You turned the table five years later, those same artists were on it, whether it was Ice Cube, Ice T, whoever.

They were like, “It’s time to cash out” as well. I think from an artist’s standpoint, the word “crossover” doesn’t mean what it used to. Every artist is trying to get it. Any artist on the planet right now; the hottest underground or the most pop or anything in between—you offer them a Sprite deal, a McDonald’s deal, a Nike deal and they’re taking it. That’s where the game is at now. I think we’ve been mentally trained as artists to think that way.

I think it started with [Diddy]. I honestly think [Diddy] is where it started. I remember watching him in 1997 and seeing how he took things from here to there. It really went somewhere else. I remember getting up every morning, getting ready for summer school in 1997 and seeing [Diddy] just running TV, running VH1. I knew at 14, this was about to be something else. I saw it.

I think from an artist’s standpoint, the word crossover doesn’t mean what it did. From a fan’s standpoint, the people still look at it that way. Like, “You’re about to crossover. We’re about to lose you. You’re about to do something else.” I don’t think it should be looked at it that way.

As long as the artist keeps it somewhat within the same wavelength while still expanding, it’s just bringing more people to believe in what you believe in. That’s what the fans want when they complain about Hip Hop and where it’s at. You’re complaining because you want more people to see what you see and hear what you hear. When we go out there and grab them, what’s the problem? We’re doing that the way you want it.

DX: If [Diddy] offered you a deal today, would you take it?

Skyzoo: As long as my lawyer agrees with it. [Laughs.] I’ll go for anybody, but I’m still a huge fan of what [Diddy] has been able to do, even outside of the music. Even when the music ain’t clicking, he keeps someone else moving. My affinity for it isn’t like what it used to be back in the day, but I respect what he’s doing. I still admire who he is as a businessman; as an entrepreneur and someone who just had a vision for the culture. Someone who saw what Quincy [Jones] did way back and implement it back in the 90s and 2000s and keep it going.

Making “Speakers On Blast” & Skyzoo’s Role In “Demos” Documentary

DX: Is it fair to call “Speakers On Blast” your biggest hit?

Skyzoo: Absolutely. Without a doubt.

DX: What’s the story behind that? Where did you record that?

Skyzoo: That was at !llmind’s old crib before he moved a couple blocks away from me. He was a little deeper in [Bedford Stuyvesant, Brooklyn]. We were working on Live From the Tape Deck. I went to his crib one morning and he had this beat. He said, “I want to play you something. I made it two hours ago.” He was like, “I don’t really know. I was about to delete it.” Nobody knows the story. He was about to delete that beat. He played it and [starts making the beat with his mouth] and I was like, “What? Wait, wait. Bring that back.” We kept playing it and I was like, “Give me an hour. Let me work.”

We knocked it out. I had this idea for the hook. I was like, “Speakers on blast / Speakers, speakers on blast.” I don’t know how you do that with the machine, but whatever little buttons you got to press, do that. I’ll say it once and just hit the button and make it keep [starts repeating the hook].” That was him. The old Black Sheep. That was !llmind. He was like, “Yo, what if we put the Black Sheep joint on there? ‘Here they come, yo, here they come.’” We added that to it and that’s definitely my biggest record, hands down.

DX: What do you think made that record take off the way it did?

Skyzoo: The beat, the hook, all the ingredients that we look at nowadays as far as making a “hit,” whether it’s on radio or TV. I think it was a combination of things. Obviously, the beat. The beat was the star of the show on that one. Lyrically, I did what I did. I got busy but the beat was the star of the show, as it should’ve been.

DX: I was a big fan of the “Frisbees” video.

Skyzoo: Appreciate it. That was my man, Derek Pike. That was his complete idea. He came to me and he was like, “Remember the Nike commercial when they were dribbling, and passing, and bringing it back, and it came flying—what if we did that?” We spent the whole day at Williamsburg just throwing the frisbee around and having somebody catch it on the side and throw it back. It was cool.

DX: You seem to be the face of the Demos documentary that’s coming out. Is that a fair way to describe it? I’ve seen two trailers now. There’s one show with you performing at [onetime Brooklyn venue] Southpaw, and the way the documentary is framed, it feels more about the success of the independent artists than it does around the type of demo [tapes].

Skyzoo: No, that’s exactly what it’s about. It’s about being an indie artist in 2012-2013, and being successful—how to achieve it, how to maintain it and not let it slip away. That’s what it’s about. It’s not really about how to get on. I think Demos came from the idea of just getting your foot into the door, but it’s not really a “how to get on” film. It’s more so why being an indie artist makes sense, why you shouldn’t be afraid of it, and why everybody’s doing it. Things like that and just the ins and outs of it—whether it’s reaping the benefits of more money on the dollar, or the other side of it where it takes those dollars to get in and it takes you being your own machine, and it takes you having your own Rolodex and picking up the phone and kicking it with people like you or other different media outlets. That’s what it’s really about. It’s about how to survive as an indie artist and do it well.

DX: Do you feel successful as an indie artist?

Skyzoo: Definitely. I’m not content. I don’t feel like this is it. I don’t feel like I’ve done so much where I can just sit back and chill, but I’m definitely successful. I haven’t worked a real job in almost seven years. With that being said, I’m definitely blessed to say that I wake up in the morning and just make music for a living, travel the world, get free clothes, get free gear, get paid to see the world, get paid to travel and take pictures in front of different monuments, different cities, and have fans. More so than anything, get paid to tell stories and share what I know and where I’m from, and what I’m about with people who’ve never stepped foot in my area or my environment. Hearing people come up to me everyday and singing the praise—I don’t take it lightly. As much as it happens—whether it’s on Twitter, or on the street—I don’t take it lightly at all. Everytime somebody says it, it means the world. From the greatest writer of our generation to favorite emcee over the past five years, to your writing helped me get through this, that and the third. I don’t take any of it lightly. It means something to me.

DX: Share a few words on Band Practice the series.

Skyzoo: The Band Practice series was a way for me to continue to promote [my recent show at MIST Harlem] and give fans new music at the same time, as opposed to just putting a flyer up on the site everyday. It was really about being able to get fans new music and giving them the sense of getting excited; to freestyle over Jazz compositions and Jazz beats and records that are Jazz samples and they flip or replay it. That was really the idea behind it. It was something I’ve wanted to do for a while—rhyming over Jazz. I was looking over Miles Davis records to rhyme over, but his records got a little too much [starts clapping]… I’ve always wanted to rhyme over straight Jazz records. I took a Jahlil Beats joint, “Range, Rover, Rhythm”—which was synths, 808s and bass—and I added a lot of trumpet to it.

A lot of people doing reviews on [A Dream Deferred] thought the trumpet on the hook was a sample. That was my man OJ who came to !llmind’s crib and played “Trouble.” I wrote the section with him. I said, “When you do it, go [starts humming the melody].” We wrote the whole melody together. I’ve been incorporating Jazz for a little while now because I’m a Jazz head. With the Band Practice series, it was a way for me to just dumb out on straight Jazz records. It was just a way for me to get busy and not cater to the beat or not rhyme about stuff that Jazz artists may want me to rhyme about. I still rhyme about the same things I want to rhyme about but make it fit and make it work. The Band Practice series is dope. 

RELATED: Skyzoo f. Talib Kweli “Spike Lee Was My Hero” [VIDEO]