"Try Again" (2000) Romeo Must Die soundtrack
Hot 100 peak: #1
Overall score: 9.45 High score: 10 (11x)/Low score: 7 (1x)
Arguably Aaliyah's definitive song, this Timbaland-produced dance cut has an interesting legacy: It is the first track to ever top the Hot 100 solely on the basis of radio airplay. Serving as the lead single for the soundtrack to Romeo Must Die (Aaliyah's first starring role in a film), it was the singer's only #1 hit. "Try Again" remains one of the standouts of Aaliyah's catalog, having been mentioned by Rolling Stone, Pitchfork and VH1 as one of the greatest songs of the 2000s. It also earned a Grammy nomination for Best Female R&B Vocal Performance and won two VMAs. Though voters awarded "Try Again" only two scores under a 9, it wasn't enough to overtake the even more beloved track that topped our countdown.
"Are You That Somebody?" (1998) Dr. Dolittle soundtrack
Hot 100 peak: #21
Overall score: 9.63 High score: 10 (13x)/Low score: 8 (1x)
When you think of Aaliyah, what comes to mind? Probably her epic creative relationship with Timbaland, the tragic plane crash that took her life...and that damn baby cooing! Taken from electronic musicians Perrey and Kingsley's 1966 experimental track "Countdown at 6," the instantly distinctive sound helped form the groundbreaking sonic playground for this tale of an unexpected pregnancy. Upon its initial release, "Are You That Somebody?" was a huge breakthrough for Aaliyah, earning her first Grammy nomination (for Best Female R&B Vocal Performance) and becoming her first single to cross over to the top ten on pop radio. (In the middle of its chart run, Billboard changed its rules to allow airplay-only songs on the Hot 100, where it then peaked at #21.) Easily the most critically acclaimed entry in this rate—having been singled out by Blender, Spin, The Village Voice, Pitchfork and Rolling Stone on various best-of lists—it was perhaps only appropriate that "Somebody" would emerge as the winner. And with just one voter rating the track less than a 9, it had this countdown in the bag.