In 2008, “Uncle Louie” Gregory decided that the world needed the Fat Boys again. Passionate and determined, to spotlight the Fat Boys’ music he discovered an entire new music industry from whence he came into “back in the day.” Louie entered the music industry as an aspiring artist at the time when he many of his would-be clients reigned supreme.

From the very start of his career, the man has intricately created companies, Uncle Louie, LLC and Uncle Louie Music Group whom have represented some of the top “Who’s Who” in classic Hip Hop. Calling himself “the CEO of the old school,” Uncle Louie has maintained business relationships and clients extending from the Fat Boys, Kurtis Blow, Special Ed, Dana Dane, Eric B., Das EFX, Onyx, and J.J. Fad, and others

Louie’s strategic social media planning and progressive outside of the box business savvy thinking has established his brand while celebrating and spotlighting Hip Hop at its best in 2011. On Twitter alone he has reached well over a 80,000 plus followers, and helped bring ’80s and ’90s Rap royalty to the digital age. He is the owner of the Fat Boys trademark and has clothing lines featured in Urban Outfitter, Hot Topix, Spencer Gifts, and JC Penney.   

Outside of Hip Hop, Louie works with athletes and celebrities such as Chuck Knoblauch, Frank Trigg, LaVar Arrington, and Bill Goldberg. On December 2, Louie will co-produce The Platinum Legends of Hip Hop and R&B in Raleigh, North Carolina. There, many of Louie’s clients and associates will take the stage in what the creators hope will be an ongoing tour opportunity. The man who’s keeping crowds chanting and fans following for many of Hip Hop’s greatest spoke to HipHopDX about his methodology and reasons for keeping the culture flag waving.

HipHopDX:  You’ve been in the music industry for years and have seen a lot. Share with us how you pushed your way through.  

Uncle Louie: It’s funny because when I wanted to be in the music business, I wanted to rap. Back in the day I was the man, best freestyler, best beat-boxer, but fortunately I grew out of that. [Laughs] I can remember having competitions and beat-boxing and finally taking it to the next level. I got to record [in a studio] and get a record deal. Eventually, I crossed paths with Mark Morales, better known as Prince Markie Dee [of The Fat Boys]. I got in the studio with Mark and he taught me, as far as being in the studio, production, and music. Mark taught me everything I knew. He later advised me to have a skill that I can fall back on. I didn’t want to accept that, because all I wanted to do is rap.  

DX: Of course, but now you’re a key deal-maker for old school Hip Hop acts… 

Uncle Louie: Yeah…By taking what I knew from music obviously was making money. I started to take my money and establish businesses, which gave me an advantage over the people who were not smart with their money. When the music stuff slowed down I had something to fall back on.  

But on the flip side of the coin, now picture me, I was very lucky, I had Prince Markie Dee on one shoulder and Eric B. on the other shoulder giving me advice. Eric B. has been my mentor since I was 16 years old. Whether I want to accept his advice or not, he tells me the truth, “This is what you need to do, don’t sell your self short.”

DX: You were surrounded by legendary people. You learned a lot, how did you apply what you learned to the Uncle Louie brand? What compelled you to involve yourself in the various services you provide artists which ranges from management to security?

Uncle Louie: Eric B. & Rakim they are legends in Hip Hop and legends in their own right. To me, I’d love to put it on the record, Eric B. was behind Eric B. & Rakim and [historians and media] feel that Rakim [deserves] all the shine. Granted, [Rakim] is a dope emcee, but without Eric B. there is no Eric B. & Rakim; which it’s evident post Eric B. & Rakim because Rakim can’t sell more than 20,000 records. Eric had a vision with Eric B. & Rakim. He needed a “Rakim.” What Eric had was a business plan; he followed it through and made a brand. That’s what Eric taught me have a plan, a clear idea of what you want to do, and don’t compromise it.  

So I asked myself, “What can I give to these guys?” My first reaction was, “Nothing.” Then I realized my gift is being able to come up with a concept that will best accomplish what everyone wants and how to tie in today’s technology to work towards our goal. Now these guys came up in the old school. I worked with Kurtis Blow, Special Ed, Dana Dane, Das EFX, Onyx, Fat Boys, Eric B., so many of these guys. But what they are missing is what comes natural to people of today and that’s technology.  

When I got back heavy in the entertainment industry, two to three years ago, MySpace was the new thing. I remember I had basically begged and pleaded with Kool Rock Ski and Prince Markie Dee for the Fat Boys to get back together; the world needs them. I met with all of these labels and resented them.  

The record labels were saying to me, “How many friends do they have on MySpace and how many views do they have on YouTube?” I said, “Yo! Who cares, it’s the Fat Boys. Haven’t you seen Disorderlies? Don’t you have this t-shirt?” So me, in my head, “What the hell is MySpace or YouTube?”

To us, if we wanted to sell records, we put out the records. So I made sure to learn all of those sites, by the time I did that, it was over.  By the time I learned MySpace, Twitter pops up. It was a wrap after that.  

So in the process a lot of these guys began to know who I was. People who knew me before found me again and people who heard of me got to know me. I just used that celebrity to promote my clients.  

DX: You’re passionate about Hip Hop and the artists whom shaped it. How do you feel about Hip Hop now?

Uncle Louie: I realize when you hear old school, you think of old school Hip Hop. Hip Hop doesn’t respect their roots. But old school is more than that, it’s a feeling, it’s a gap of time, it encompasses everything.  Do you know what Hip Hop is missing?  

Hip Hop is missing a message. I think that it’s disrespectful when promoters want to pay old school acts like the Fat Boys, which have made their money in the past, $3,000 or less, while they will easily will sell thousands of tickets and make well above what they paid them [acts]. It’s crazy.    

I worked with J.J. Fad and saw some of the same things. Everyone knows who Fergie is, but do they realize that her song “Fergalicious” was an interpolation J.J. Fad’s, “Supersonic.” You would think since she made $30,000,000 off that song. You would think that she would have looked out for those girls. Doesn’t work that way; I think that she paid them like $15,000. If I made that much money off someone else’s hard work, I might have to send you a card or something. [Laughs] At the end of the day, I want to do what’s right. That’s greed, to me that’s greed if you don’t care about the people who put you in that position. I don’t want to preach too much.  

DX: Yeah, that’s something that has been happening and continues to happen a lot. A quick side note, what’s with you and ?uestlove; you guys seem to go back and forth on Twitter. 

Uncle Louie:  I go back and forth, on Twitter, fighting, with ?uestlove. I think he is disrespectful. He had the 25th anniversary of Eric B. & Rakim’s Paid In Full and he didn’t even invite Eric B. How can you do that? You know? And oh, by the way it’s only been 24 years; next year will be 25 years. You can quote me. I don’t care for ?uest. He’s a dick. It’s people like him that take advantage of the situation. How can you celebrate Eric B. & Rakim and not invite [both of] them to the celebration?

DX: So to you, in your perspective, who do you think in present-day Hip Hop now embodies Hip Hop?

Uncle Louie: Wow! Diddy comes to mind. I’ve always loved what he’s done to reinvent himself, which is hard to do. I like what’s he’s done as whole; the same for Jay-Z. He epitomizes the success of a Hip Hop artist to me: the ability to reinvent yourself in the entertainment industry is what makes you successful.  

DX:  Whom do you feel is unfairly treated, as far as legacies go in Hip Hop?

Uncle Louie: It’s funny I talk to Vanilla Ice on regular basis and over the years he has to be the most hated on, but that guy is such a gentleman when you talk to him. He is playing shows all the time. To me that’s awesome.  

DX: What are you looking forward to working on now?

Uncle Louie: Right now, I’m working with [wrestler] Bill Goldberg. He reached out to me and we started just working. I’m also preparing to launch several projects with Cowboy Troy, of CMT, that will bridge Hip Hop and Country music. We’re gonna take 12 Hip Hop classics and perform them with a live band; with the fiddle and all the trimmings. It’s going to give the Country fans who don’t know Hip Hop the chance to hear these classics. Imagine how many more people that haven’t heard some of the Hip Hop classics we’ve heard. They will get a chance to hear them in their favorite genre, Country. It’s going to be great and they’re going to love it! I’m planning on setting up a tour in [Las] Vegas for this project and bring some of the legends to come along with us. I’m thinking outside of the box.

Purchase tickets to December 2’s The Platinum Legends of Hip Hop & R&B in Raleigh, North Carolina.