Gillie Da Kid took a trip down memory lane during his sit-down with Shannon Sharpe on Club Shay Shay, opening up about pivotal moments in his career—from a near deal with 50 Cent to his experiences with Cash Money Records.
The Philadelphia rapper recalled being en route to meet with 50 Cent, who was interested in signing him, when a conversation between DJ Cosmic Kev and DJ Khaled took an unexpected turn. Khaled questioned whether Gillie was still beefing with Lil Wayne, a topic Gillie felt was irrelevant. He emphasized that he never starts problems but reacts aggressively when provoked. “Anybody I ever had an issue with, they started it,” he said, adding that when he retaliates, he doesn’t just throw jabs—he aims for a knockout.
Gillie also reflected on his early career, mentioning how he didn’t initially aspire to be a rapper. His original dream was to make it to the NBA, and he only started rapping in college for fun. However, a robbery incident led to his expulsion, and upon returning home, he realized his talent. His fourth-ever song, Love for Gilly, became a No. 1 hit on Philadelphia’s Power 99, putting him on the radar of major labels, including Def Jam, Atlantic, and Priority Records.
He eventually signed with Tony Draper’s Suave House Records, calling Draper “the realest CEO” he ever met. He recounted how Draper introduced him to the lifestyle of successful rappers, from luxury cars to immaculate mansions. But despite the success, another opportunity arose when Cash Money Records came calling.
Gillie detailed how his performance at a Cash Money show caught the attention of Birdman, who immediately offered him a deal. Still under contract with Suave House, Gillie ensured that Cash Money compensated Draper before signing. However, issues arose when Cash Money sought to acquire his publishing rights. While other artists on the label had their publishing controlled, Gillie stood firm, refusing to give it up. “The number they were offering and the number I wanted were two different things,” he explained. As a result, he found himself shelved by the label, ultimately leading to his departure.
