Album: Romeo Must Die Soundtrack (2000)

Aaliyah had been out of the spotlight for almost two years when “Try Again” dropped, broke records, and became the only No. 1 hit on the Billboard Hot 100 of her career. But “Try Again” was less about accolades, and more about her and Timbaland breaking boundaries again with a comeback single. Quoting Rakim’s “It’s been a long time/I shouldn’t have left you,” Timbaland kicks off the distorted, triumphant, acid-house-inspired track which served as the lead single off the Romeo Must Die: The Album soundtrack, which Aaliyah starred in.

“Try Again” was the first single to reach No. 1 on the Billboard Hot 100 based solely off the strenght of radio airplay, and solidified Aaliyah as one of the most successful pop stars in the world. But Aaliyah, and Timbaland both knew they wanted to do more than recreate the bubblegum pop records of that era, and utilized a mixture of hip-hop, early electronic dance music of the ‘00s, and R&B to create massive hits, like “Try Again.” The production itself was a look into what was to come for Timbaland over the next decade, as well. —Lauren Nostro