Title(s): Birdman - Co-founder of Cash Money Records
Lil Wayne - CEO of Young Money Entertainment
Artists They Worked With: Lil Wayne, Juvenile, Mannie Fresh, Drake, Nicki Minaj, Tyga

Cash Money and Young Money represent two virtual generations of hip-hop talent. It stands to reason that the men behind each imprint — Bryan “Baby” Williams and Dwayne “Lil Wayne” Carter regard each other as “father and son.”

After making some local noise in New Orleans for several years, Cash Money charged onto the national hip-hop scene in 1998 as the result of a huge, unprecedented pressing and distribution deal with Universal Music Group, brokered by Rap Coalition founder Wendy Day, who also helped launch deals for Master P’s No Limit Records, Eminem, and Twista. The first superstar of the Cash Money stable was Juvenile, followed closely by other artists like B.G. (who with Juvenile comprised Hot Boyz), Lil Wayne, and Big Tymers.

As Lil Wayne aged and ascended, Baby gave him an imprint and ostensible executive power. Whomever you believe spearheaded the creation of the roster—Baby or Wayne—it’s incontestable that Young Money broke Cash Money out of its exclusively Southern style with the signing of Toronto-based rapper Drake and New York native Nikki Minaj.