Remember That Time I Got to Interview Diggy Simmons? Yeah. THAT HAPPENED.

Daniel “Diggy” Simmons… is cooler than you.

Look, I mean that in the best way possible. He probably wouldn’t even want me to say that, that’s how cool he is. But you’ve just gotta face facts.

His sneaker line comes out in a month. He dresses better than anyone I know. His second mixtape, ‘Airborne’, drops on July 29th. He’s already been nominated for MTV’s “Hottest Breakthrough MC of 2010″ for his first and other works. Works supported by the likes of Kanye and Nas.

And he’s 15 years old.

picture: @diggy_simmons's twitter background

And believe me, after talking to him for just ten minutes, it doesn’t have anything to do with his father’s success, other than the fact that he was raised in a musical environment and supported by his family to become the driven, friendly, humble, gracious, and ambitious person that he is.

Diggy’s got “it”… you know what I mean. That thing where you just know that someone will be able to accomplish whatever they want to in life, and they’re going to make you love them while they do it.

I’ve transcribed the interview here for those of you reading at work, etc., but try to listen to the audio if you can. Writing can’t capture this kid’s personality.

Okay, y’all, bear with me at the beginning… YES I WAS NERVOUS. Jerks.

L: As a blogger and prospective Twitter Jockey for MTV, one of my favorite things about you is definitely how engaged you are with your fans on the internet. And I hear you’re pretty tight with Justin Bieber, who’s also really active online. What do you think about the way social media now allows artists to connect with their public?

D: I think it’s great, because a lot of the time, I mean, you look at- shoot- years back, the only real source for even hip hop, was just like, allhiphop.com, and now you’ve got all these blogs and ways to get involved you know, as the news occurs. Before it was just radio, which is hard, and now with Facebook, Twitter- you can be like your own publisher.

L: Absolutely, and you can have a real conversation with your fans, actually talk to them.

Oh yeah, I answer and tweet back my fans, DM them, and different things, so I think it’s great, especially when I can interact with the people that go hard for me. It’s mind-boggling to me that somebody like, takes out their day, for me. So it’s great.

L: The very first thing Twitter said when I told them I was interviewing you was: “Ask him about fashion!” You’ve become something of a style icon, and your posts about fashion on your blog are so inspiring. I know you’ve started your own sneaker line, “Chivalrous Culture”, releasing the first shoes this fall, is that right?

D: Yes, the shoes are coming out this fall, like around August/September- it’s going great.

L: So what’s your next move in the fashion world?

D: I wouldn’t mind doing some collaborations, you know, with different brands that I like. And obviously, one day, you know I already have it in mind- I’m always thinking- a clothing brand I’d like to do of mine.

L: And I can’t wait to see it. So, I read that you used Garage Band and a MacBook to produce your first tracks, which I LOVE, and you’ve said in an interview that you want fans to recognize you for your lyrics, rather than mistaking you for a “bubblegum, kiddie-bop” rapper. It seems like you really know what’s important to you as an artist- there’s no tricks, just a real person with real talent. Where does that confidence, that drive, come from?

D: I mean, I don’t know, a lot of people always ask “What is that ambition, what is it in you that’s made you always know what you wanted to do?” I mean, I don’t know. I think it’s just something that me just being young- from sketching when I was like, in the third grade, to having a sneaker line now, you know, always knowing what I wanted and what was the intention.

L: Speaking of that drive, your second mixtape, ‘Airborne’ is going to drop on July 29, 2010. How has it evolved from your first one, ‘The First Flight’? What’s different? [Get a taste of 'Airborne' here.]

D: All across the board. Lyrically, the production- it’s just bigger, it’s very album-esque.

(Aaaand my TWO cameras somehow both cut out for a minute, so make sure you go give it a listen. You won’t be sorry.)

L: You’re one of MTV’s candidates for “Hottest Breakthrough MC of 2010″. You’ve been around the music industry all your life, but only in it yourself less than a year- this be quite a ride. How did you feel when you first heard that?

D: When I first heard it… I was in the car on my way to a photo shoot, and I saw it, you know, the other names pop up, and I’m just happy to be next to these dudes that have been on the grind, and, you know, shoot- it’s just been like, a happy year for me! And it’s great to be next to people who’ve been on the grind for years. It’s only been half a year- you know, the grind- so I’ve been going hard.

L: A lot of people recognize you, I’m sure, from Run’s House, and have preconceived notions about who you are, but through the internet you’ve had the opportunity to connect with them about your point of view on all different issues- music, fashion, pop culture- and you know, has that allowed you to say, “Hey, I’m not just that 10 year old kid from a TV show, I’ve got my own identity.” How has that allowed you to separate yourself from your family, and your brother, who I’m sure you’ve been compared to?

D: Of course it’s harder, but that’s, you know, that’s something you do right here, in interviews, and through your music. You let people know, “Hey, this is just me, I’m here by myself, I’m grinding on my own.” And, you know, that’s just really how you let people know that- of course there’s gonna be the people that doubt you at first, cause there are tons of people that go, “Oh, he’s a rapper now?” Because of course there are a lot of people that are aspiring producers, and on every corner there’s an aspiring rapper, so of course to some people it must be annoying. But the people that have been supporting me, just, you know, thank you.

L: Press was buzzing after your Atlantic deal [for The First Flight] that [older brother] JoJo was jealous. We both know that’s crazy, there’s only love in the Simmons family. But is there a chance the two of you might collaborate in the future?

D: Oh, yeah, for sure. It could most definitely happen, I mean, we have done tracks a while ago that we probably wouldn’t put out, because I’ve progressed since, but, shoot, it could most definitely happen.

L: Maybe we could get the whole family in there?

D: [laughing] I don’t know about that, maybe on some ad libs or something!

Make sure to check out Diggy’s blog, Life of the Jet Setter, for sneak peeks at ‘Airborne’ as well as his fresh perspective on music, fashion and more.

You can follow him on twitter @diggy_simmons, and you can download his first mixtape, ‘The First Flight’, right here.

This kid’s going up fast… you don’t want to miss it.