Chief Keef was close to being Apple's first artist.
The article entitled, The Return of Chief Keef highlights Keef's rise to success, as well as his bumps along the way. Keef burst onto the scene with "Don't Like," a track that brought about a Kayne remix, and had every A&R in the industry focusing on Chicago's South Side. One of those executives was Larry Jackson, who at the time was executive vice president of A&R at Interscope. He flew to Englewood to meet with Chief Keef. Eventually Keef would sign and then be dropped by Interscope, only after the departure of Jimmy Lovine, who took Dr. Dre and Jackson with him to Apple Music. That's where things got interesting.
In 2015 Keef would sign with Greek billionaire Alki David’s FilmOn TV, but before that he could have been Apple's first artist. As Keef told XXL:
“This was before I ended up with Alki, messing with Dro,” referencing former manager Rovan “Dro” Manuel. “They were talking about taking me to Apple. This was before they did anybody with Apple Music. You know what Larry called me and said? He said, ‘You’re gonna be the first artist on Apple Music,’ and I turned it down. Because, you know… I don’ know. I just didn’t do it. But I would have been the first artist on Apple Music.”
Jackson also confirmed his intentions to sign Chief to Apple, “We had a conversation about it,” confirms Jackson, “but Keith has always been enigmatic, and I didn’t even expect him to leap at it. I didn’t feel slighted because I know he’s so enigmatic, and often times you think he’s gonna go right and he goes left.”
What a major deal that would have been for Sosa, but timing and circumstances of course are everything, and despite that Chief Keef is still an artist we always check for.