The Single: "Lollipop"
The Album: 2008's Tha Carter III
The Reaction: This was a risk for Wayne. At the time, he was on top of the rap world and this was, well, not really a rap song. It was pop-driven and featured Wayne setting his sights on the top of the Billboard charts. But, somewhat surprisingly, it was a hit. Credit Static Major for doing his thing on this and Jim Jonsin for the solid production effort.