Label: Roc-A-Fella/Def Jam/Jive
Key Track: "Green Light"

The ill-fated collaborative album from these two legends is understandably overlooked, but we'll say it—this would be considered a classic if video of R. Kelly (or a guy that looks a lot like him, in a house that looks a lot like his) peeing on teens hadn't leaked weeks before the LP's release. 

As the album began to leak, R. Kelly's alleged underage sex tape was serviced to the media, causing Jay Z to disown the project.