Photo: Gage Skidmore / Wikimedia Commons (CC BY-SA 3.0)
Released in 2006 as the lead single from Timberlake's second solo album FutureSex/LoveSounds, "SexyBack" marked his full transformation from boy-band frontman to solo pop innovator. Produced by Timbaland, its distorted electronic sound was a sharp break from the smooth R&B of his debut.
The song debuted at No. 1 on the Billboard Hot 100 and stayed there for seven weeks, becoming one of the defining hits of the 2000s. It later won the Grammy for Best Dance Recording — proof that Timberlake's solo gamble had paid off.