86. Aaliyah, 'Try Again'
It's hard to believe there was ever a time when people complained that Timbaland wasn't making enough records. But Tim made a grandiose re-entry here, quoting Rakim: "It's been a long time/I shouldn't have left you." Aaliyah's chiller-than-chill vocals make it still seem painful that this brilliant R&B princess died so young — yet managed to make so much unforgettable music in her time.