Producer: Timbaland, Timberlake, Danja
Album: FutureSex/LoveSounds

After accomplishing the tricky transition from standout boy band talent to affable R&B heartthrob at the beginning of the 2000s, Justin Timberlake crossed another important cultural boundary with his sophomore album and its standout single "My Love": the division between pop music and art.

Produced entirely by Timbaland and his mysterious protege, DanjaHandz, FutureSex/LoveSounds proved that hip-hop no longer had a monopoly on urban music innovation. The aggressive house-pop lead single "SexyBack" was perhaps too ahead of its time for R&B fans, but the floating, trance-tinged follow-up, "My Love," marked the beginning of black radio's impending flirtation with electronic dance music.

The most unexpected reaction to "My Love" came from the historically pop-averse white hipster world. Pitchfork named it the best song of the year, and the Hollertronix message board community ravenously embraced the song when it leaked to the internet in the summer of 2006. The obscure phrase "Atlantic Records for T.I. Clearance"—the label voiceover that watermarked the original MP3 leak— even inspired a t-shirt and multiple D.I.Y. remixes. Six years later, it's hard to imagine the current avant-garde R&B scene existing without Timberlake's genre-conflating success.