Album: One in a Million (1996)

You can't argue with the pairing of Aaliyah and Timbaland. Her irregular R&B vocals, marked by subtlety and restraint rather than tremendous range and insane melisma, suited the jittery beats produced by the Norfolk, VA native. "Heartbroken" isn't one of their most famous or noteworthy collaborations, but it still trembles and knocks in all the right ways.

On the ballad, from the back-half of One in a Million, Timbaland's drums fill out the space surrounding the low, shifting two-tone synth hum that serves as the song's backbone. "What made you go and run this game on me?" Aaliyah sings. She's tired of being the more loving one in a lousy relationship. She's tired of having her heart broken. The la-la-las that float around the chorus are some of the sweetest syllables she ever sang. —Ross Scarano