Label They Almost Signed To: Roc-A-Fella
Label They Ended Up Signing To: N/A
Circa: 1999

Big L is a hero of underground rap. After putting out his debut album Lifestylez ov da Poor & Dangerous, Columbia Records dropped the Harlemite. Working with his own label, Flamboyant Entertainment, L caught the attention of Jay-Z and Dame Dash of Roc-A-Fella Records. According to Big L’s brother, Jay and Dame Dash courted L heavily. However, the signing was delayed as L would only sign if fellow Flamboyant Ent. artists like Herb McGruff would be signed as well. L's brother told Vibe that, "I think they would have worked something out, but L’s life got cut short." This possible partnership between two of hip-hop’s greats makes the “what if” questions surrounding L’s early passing all the more painful.