Producer: Jim Jonsin, Deezle
Album: Tha Carter III

On “Don't Die,” a cut off Lil Wayne and Baby's Like Father, Like Sonalbum, Wayne declared, “And just think, I'm one sell out record away from being famous.” That sell out record was “Lollipop.”

After months of auto-tune experimentation on mixtapes, the hip-hop world knew that Weezy was going to come with something different on Tha Carter III. He didn't disappoint with the album's lead single, a naughty electro anthem designed for crossover success.

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.

After this broke down the "rappers aren't allowed to sing" barrier, a slew of creatively hungry MCs tried their hand at crooning. Still, no one can make an R&B record like the best rapper alive.