Lollipop by Lil Wayne feat. Static Major (2008)

Lil Wayne's first number one, the biggest song from Tha Carter III, the album that made him the most famous rapper alive in 2008, is a slow, Auto-Tuned request that a woman treat him like a "lollipop". That is the metaphor, the hook is the metaphor and the song is the hook. It spent five weeks at number one and won the Grammy for Best Rap Song, which means the Recording Academy, in evening wear, handed a trophy to a lollipop.

Static Major, who co-wrote it and sings the hook, died of complications from a medical procedure a few months before it reached number one and never saw it become a hit. That gives the record an unexpectedly sad afterlife for something this playful, and it is one of the reasons Wayne has kept performing it for so long.

Its other afterlife is a lineage. 50 Cent had offered the same "lollipop" in Candy Shop three years earlier; Flo Rida would swap it for a "whistle" four years later. Three sweets, one idea, and Lollipop is the version that proved the idea could win a Grammy without the actual word being spoken once, a landmark moment for the confectionery-industrial complex.