Album: Dr. Dolittle Soundtrack (1998)

Aaliyah's oeuvre was an exercise in self-awareness. Her first two albums carefully toed the line between adolescence and adulthood, displaying a woman exploring the terrain of love, trust, and lust; one who exuded a playful innocence while hinting at a more sultry side. Her crowning achievement, a collaboration between her, Timbaland, and Static Major, "Are You That Somebody," would capture all of that perfectly. "Sometimes I'm goody goody, right now I'm naughty naughty," she sang in her light breeze of a voice.

No one producer working in the '90s pushed R&B to its limits quite like Timbaland. Here, he honed in on his patented eccentricities and delivered a claptrap of a beat with stuttering guitar licks and percussion consisting of deft beatboxing. There's also a sample of a baby (taken from Perrey and Kingsley's "Countdown at 6") that manages to worm its way into your head. It all sounds like too much for one person, let alone someone as vocally demur as Aaliyah, to tackle. But she fares more than well, pacing herself perfectly along with the clicks and ticks; licks and infant laughs.

To many, Aaliyah was nothing more than a vessel for her producers. But here, on this track that managed to only hit No. 21 on the Hot 100, she was every bit a part of the process as her masterful producers and songwriters. It was Aaliyah her most self-aware-as an artist and an individual. It was Aaliyah at her most Aaliyah. —Damien Scott