3. Lil Wayne f/ Static Major "Lollipop" (2008)
Producer: Deezle, Jim Jonsin
Album: Tha Carter III
Label: Cash Money, Universal Motown
Love it or hate it, "Lollipop" is Wayne fully unhinged, yet somehow able to fit into a pop song formula. It's one of the strangest and most abrasive ballads to ever hit the airwaves, with all empty space and drug addled Auto-Tune mumbles. That it's Wayne's biggest hit is an oddly appropriate contradiction.
Here is a scrappy troll of a gangsta rapper turned into a sex icon, singing passionately with a singing voice that would be atrocious had it landed in anyone else's body. But he sells it on presence and persona. And, yes, today you aren't going to ride around with your homies listening to "Lollipop," not just for any implications but because the song is dangerously played out.
So consider instead the very slept-on remix, which keeps the beat and the Auto-Tunage, but runs three strong verses of actual rapping through it all. Kanye makes a big show about how he's not going to let Wayne murder him on this track. 'Ye sounds great, playing the scrappy underdog position where he's most comfortable, but none of that stops Wayne from still basically murdering him with the verses that follow.