S.K.Y Entertainment was established in the summer of 2002 as Skyline Entertainment with 8 artists and one producer, collectively known as the A- Team. During the summer of 2002 the A- Team built a recording booth and began to record music using Fruity Loops, Cool Edit and Acid Pro. In the process 2 Full Albums were recorded. A Labratz album and Black Jez’s From the Darkness to the Light (2002).

In 2003 S.K.Y picked up 3 new artists, Fireboy, Blaise B. and Plila. Fireboy’s effortless delivery, Blaise’s insightful pen, and Plila’s all around talent were the last pieces before S.K.Y Entertainment’s trek towards the music industry. In August 2003 the A- Team collaborated on We Got Now, a local smash on the North and South sides of Chicago. The A- Team followed that with 3 solo mixtapes and the classic Business First (winter 2004), that sold approx 3000 units. The A- Team ended the year performing at Chicago’s Unsigned Hype tour with, Lupe Fiasco, Boolumaster, Malik Yusef, Grimmyville, and Cap One.