Flying Over New York Entertainment started and got founded in 1998 by a couple named Adam Smith and his soon to be wife, Rosanna who met and dated while at work aboard a luxury cruise ship "MV Royal Majesty". Adam Smith aka DJ Cool A.D. was a guest disc jockey contracted with "Gino Gambarto CEO of Ship Services International", while Rosanna was a bar waitress and aspiring bar manager from The Philippines. In June of 1997 Adam and Rosanna discovered they were going to become parents. At that point DJ Cool A.D. then began to work out a plan to keep his career progressive and be able to spend quality time with his family. It wasn't too long before they came up with the plan and started laying down the ground work for Flying Over New York Entertainment. While still on board the ship he started making contact with his friend DJ Psycho D and other business contacts he have made from the clubs and radio stations he has played.

In April 1998 Adam and Rosanna became proud parents of a baby boy, born in the Philippines. Adam received the word of his child's birth and took an emergency Flight back to New York City to start the ball rolling. The next day Flying Over New York Entertainment was born. DJ Psycho held it down on the 1's and 2's while Cool A.D. was working on 3 aspects of business. 1-Major promotion, 2-Trade marketing and 3-Obtaining business lincenses. The business was running well.

While the business started to grow it started obtaining more mobile parties (Weddings, Birthday Parties, and Bar/Bat mitzvahs). Adam had no real idea of what would be expected from prospective clients looking for a disc jockey for these types of events. It really through him for a loop when they would ask him what is his playlist. He remembers the first time that question was asked. Adam states "I was in the Flying Over New York Office with a client who was looking to hire us to do a wedding reception. The bride-to-be asked me: do I have my song list written out so that she could see if I covered her type of music? I was stumped because I am a radio station and night club DJ. I get boxes of music every day from record companies and pools. I replied to her we get every song that comes out and we have almost every song that ever came out. There is no way possible to get all of our music on a paper list. Of course you know that we didn't obtain that contract!!!!". Over the years people did realize that the DJ's at Flying Over New York Entertainment really did carry the largest selection of music anywhere.