Date: May 2008

The first single from Tha Carter III, “Lollipop,” catapulted Wayne to unprecedented pop star status. The song featured Wayne singing in Auto-Tune and went on to win a Grammy for Best Rap Song in February 2009.

To capitalize on its success, ‘Ye jumped on the official remix alongside Wayne’s new set of bars. In the end, the pair delivered another hot record, with Kanye acknowledging his need to rap well to keep up with a then on-fire Lil Wayne ("You ain't finna murder me like everybody else").