Label They Almost Signed To: Def Jam
Label They Ended Up Signing To: Young Money, Cash Money, Republic
Circa: 2005

It’s hard to envision Cash Money Records without Lil Wayne. But the rapper, who initially signed with Baby and Slim Williams New Orleans-based independent shop when was just 11 years old, almost left in in 2006. During Tha Carter II era, Wayne was reportedly in discussion with his idol Jay-Z’s Roc- A-Fella Records. According to Lil Wayne, Jay-Z expressed interest through a phone a call, but never provided an actual offer.

In a recent interview with Power 105’s Breakfast Club, Jay said that, after the conversation with Wayne, he’d called Baby to discuss the situation, but was immediately contacted by a lawyer demanding he put a halt to the proceedings. “I would rather lose that situation and do the right thing than the opposite,” Jay said. “’Cause I think I could have signed him and then told them after. But I did the right thing and I’m cool with that decision.”

Since then, Jay and Wayne have engaged in some low key beef-on-wax with tracks like “It’s Good,” “H.A.M.,” and most recently, “La Familia.” So it’s harder than ever to imagine them kissing on the mouth.