Rihanna
Back in 2006, Jay Z was skeptical about signing Rihanna to Def Jam because he was unsure if Rihanna would release another massive hit. It was a risky move for him because of the success of “Pon de Replay.” He said, “When a song is that big, it's hard for a new artist to come back from. I don't sign songs, I sign artists". However, she released several chart-topping singles, including “Umbrella,” with her then boss. The song talks about a platonic connection transforming into a romantic relationship, despite the stormy weather. The pop and R&B record won a Grammy award for Best Rap/Sung Collaboration. Jay worked with Rihanna again, but this time with Kanye West on the number one record, “Run This Town,” for his eleventh studio album, Blueprint 3. The single received two Grammys for Best Rap Song and Best Rap/Sung Collaboration. As you can see, Jay Z makes excellent music with the Barbadian Princess.