Discovered by Grammy award winner KayGee, rapper Rob Jackson first appeared in 2002 with a series of hit singles. Coming from Lexington, Kentucky, a state not normally known for much music presence in hip-hop. Rob changed the game and made history for Kentucky artists. Check out his full interview below and be sure to Follow Rob on his Instagram.
Interview:
Where are you from and how was life growing up? I was born and raised in Lexington,Ky. I had the average upbringing of most Black kids from the area that grew up in the 80’s and 90’s. Little money but lots of love and support. I always had a love for music as well as reading and writing. Those things combined probably led to my rap career.
Describe the feeling of having your first big hit single? It was an amazing feeling. Consider the struggle it was to break into the business back then coming from a place like Kentucky in the pre-internet with no youtube or soundcloud or anything like that. It was an amazing task just to be heard back then. I felt pride and sense of putting my city on the map because nobody from here had ever done that as an artist in hip hop. The entire state for that matter. I feel like a large part of the legacy that made it possible for the Jack Harlows and the other current artists from KY doing their thing.
How did the rap name come to be? I never came up with a rap name that I really felt comfortable with so I just decided to go with my real name. It wasn’t a popular choice at the time. There were very few rappers that had made the decision. I felt like it made me stand out at that point. It’s fairly common now tho.

Where does the inspiration come from for creating music? I was always a creative kid. In the late 80’s which is now considered the golden age of rap, I just fell in love with the art form. It was the dopest thing I had ever seen. So many different styles. So many super talented people. Even tho I didn’t see anybody that came from where I was from, I made a decision that was going to set out on a mission to make myself good enough to be among those guys that I looked up to one day. Fortunately I was able to do it.
What artists inspired you the most and who do you currently listen to? There was a long list of rappers and song writers that I admired and studied. People like Nas Biggie JayZ Scarface Redman Special ED Outkast UGK Sade Bill Withers Phil Collins and more. I studied them all for years to find out what I thought was dope about each one of them. Then I stole it! When you put all those borrowed attributes together at once it makes a totally new combination of skills and a unique style. That was my approach, It was very scientific. If you study my music and you know what to listen for you can hear all those influences.
How did Arista Records discover you and what was your relationship like with KayGee? A college friend of mine that happened to be from New Jersey dropped my demo off at his offices one time when he was home on break. His brother listened to it and brought it to his attention. I was already back forth to New York living in my car and battling people on the street. I was taking whatever label meetings I could get from just building my reputation on the streets of New York. KayGee had a label deal at Arista so brought me to LA Reid who was the president of the label at the time. We hit it off once he found out I was from Lexington. He was from Cincinnati and had been to Lexington many times. Him and the VP Mark Pitts( who used to be Bigge’s manager) decided to sign me and the rest is history.
Describe your experience with the music industry: The industry was much different than I expected. I found it was a lot less about talent than I would have guessed. It was more about relationships than anything. This is how being outsiders from KY put me and my team at a disadvantage. There was nobody from our area to link with or mentor us. We basically had to learn on the job. We figured out a lot of things and made some good relationships but it was much harder for us. We made some mistakes understandably. From a creative standpoint I found I was much more prepared to compete than the average rapper. The journey of being from Kentucky forced me to develop my craft to a different level and caused me to be more hungry and humble than others. When it came to actually making music I had an advantage. I was more prepared than most.

What kind of support do you get from your home town/state? Being the first artist to do what I was doing made it hard for the hometown to support the movement we were trying to create, They had never seen anyone make it before and didn’t really know how to get behind it. Don’t get me wrong there was much love and support at the street level. But we were trying to build a movement and put the infrastructure in place that would create a path for others to make it. Many of the other artists did not understand that process and it made it difficult. In my opinion that is part of the reason why it’s 20 yrs later and nobody else from the city has made that kind of impact at the industry level.
If you could collaborate with one single artist who would it be and why? I got to work with a lot of my favorite artists. UGK Ceelo Green Boyz to Men Pastor Troy Lil Jon Pink Freeway Lupe Fiasco Kanye Yo Gotti and the list goes on. I would love to work with Nas or Jay. Pac or Biggie. Any of those guys.
Favorite Artists of all time and why? I love too many artists for too many different reason to pick a favorite
What advice would you give to inspiring artists? Really just focus on the craft first. It might not seem like right now, but really knowing and understanding the science and the process of making quality music will carry you far. Also focus on relationship building and understanding what that really means in the business sense. It’s not a real relationship unless the interactions are mutually beneficial. It’s very important to learn to operate inside that mental space.
