The 2000s File Feature
Try Again
Try Again: Aaliyah's Number One and the Sound of What Might Have Been The Princess of R the context around it is heavy. You can hold both of those things at …
01 The Story
Try Again: Aaliyah's Number One and the Sound of What Might Have Been
The Princess of R&B at Her Peak
There is a particular kind of weight that comes with listening to an artist who was clearly still ascending when they were taken. Aaliyah Dana Haughton, who recorded and performed simply as Aaliyah, was 21 years old when "Try Again" began its chart run in the spring of 2000. The music she was making at that point was among the most artistically adventurous in mainstream R&B, and "Try Again" was its clearest and most commercially successful expression. It reached number one on the Billboard Hot 100 on June 17, 2000, and it stayed there long enough to confirm that this was not a fluke but a genuine peak. She died in August 2001 in a plane crash in the Bahamas. The chart history of "Try Again" is now inseparable from that grief, but the song deserves to be understood first on its own musical and commercial terms, as the work of an artist at the height of her powers.
Aaliyah had been recording professionally since she was a teenager, releasing her debut album at 15 and her second album, One in a Million, at 17. That second album, produced primarily by Timbaland, established the sound she would pursue throughout her career: forward-thinking R&B that borrowed from electronic music, hip-hop production techniques, and international influences to create something that felt genuinely new rather than merely competent. "Try Again" arrived as the fullest realization of that sound.
The Timbaland Collaboration
"Try Again" was produced by Timbaland, who had been reshaping the sonic landscape of R&B and hip-hop since the mid-1990s through his work with both Aaliyah and Missy Elliott. The production on "Try Again" is a demonstration of everything Timbaland was capable of at the height of his creative powers: unconventional drum programming that defies easy categorization, synthesizer textures that feel simultaneously alien and contemporary, and a production philosophy that treats silence as an instrument with as much expressive potential as any other element. The beat breathes in ways that conventional R&B production of the era did not. The song appeared on the soundtrack to the film Romeo Must Die, which starred Aaliyah and helped provide commercial context for the track's rollout to radio and video platforms.
The Chart History: From Debut to the Summit
"Try Again" debuted on the Billboard Hot 100 on March 18, 2000, at position 59. Its climb was steady and purposeful, moving through the fifties, the forties, the thirties, the twenties, and the teens before reaching the summit in June. The song spent 32 weeks on the Hot 100, a remarkable run for any song and an extraordinary one for a track this sonically adventurous. The single was notably the first song in Billboard chart history to reach number one based entirely on airplay without a corresponding commercial single release, a distinction that reflects both the shifting economics of the music industry in 2000 and the genuine, extraordinary enthusiasm radio programmers and their listeners showed for the track. 156 million YouTube views confirm ongoing discovery and continued return visits from listeners who know the song well but keep coming back.
What the Song Revealed About Its Moment
In the commercial landscape of mid-2000, "Try Again" stood apart from most of what surrounded it on the charts. R&B was healthy and commercially diverse, but much of it operated within recognizable production conventions that Timbaland's work consistently defied. The beat he built for "Try Again" incorporated elements from electronic music, hip-hop, and sonic influences that resisted easy categorization, creating something that felt genuinely new rather than like a more polished version of what had come before. The fact that radio embraced it without hesitation suggested that the mainstream audience for R&B in 2000 had a considerably larger appetite for sonic innovation than the industry's more conservative voices gave it credit for. Aaliyah's vocal performance met the adventurous production with equivalent control, ease, and artistic confidence.
Legacy: A Number One That Carries Extra Weight
Every number-one record carries a kind of significance. Aaliyah's number one carries additional freight because of what came after: the loss of an artist who was clearly capable of even greater things, the career that ended before it reached its full potential, the catalog that stopped growing too soon. "Try Again" now functions simultaneously as evidence of her peak commercial achievement and as a kind of monument to potential that was never fully realized. The song itself is exhilarating; the context around it is heavy. You can hold both of those things at once. Press play and let her remind you what was possible when everything was still ahead.
"Try Again" — Aaliyah's singular moment on the 2000s charts.
02 Song Meaning
Try Again: Persistence, Desire, and Sonic Courage
The Simplicity of the Message
"Try Again" delivers its central theme in a form direct enough to feel almost self-evident: if something hasn't worked, if the connection hasn't been made yet, if the relationship hasn't found its footing on the first or second or third attempt, the answer is not to quit but to try again. The song treats persistence in love not as desperation but as wisdom, as the recognition that worthwhile things typically require effort and patience and the willingness to be uncomfortable in the service of something better. That is not a complicated idea, and the song does not pretend it is. What the song does instead is invest that straightforward idea with enough sonic and emotional richness that it feels profound rather than obvious, which is a considerably harder thing to achieve than it might appear.
Aaliyah's Vocal Approach
Aaliyah's vocal performance is absolutely central to the song's emotional meaning, not merely to its commercial appeal. She sings with a controlled breathiness that makes the earnestness in the lyrics feel intimate rather than declarative, close rather than performed. She is not belting the emotional content at the listener from a distance; she is sharing it with the listener at close range, in a register that implies genuine trust and genuine vulnerability. This approach was a signature of her collaborative work with Timbaland across her recording career, and on "Try Again" it reached its most refined expression. The understatement of the performance paradoxically intensifies its emotional impact, because it sounds more like truth than like a song about truth, which is the hardest distinction to achieve and the most meaningful when achieved.
Timbaland's Beat and What It Means
The production by Timbaland is not merely a frame for the lyrical and vocal content; it carries its own meaning that runs parallel to the lyrics and enriches them. The unconventional drum programming, the electronic textures, the deliberate spaces in the arrangement where conventional R&B production would fill in with additional layers of strings or backing vocals: all of these choices communicate something about the emotional territory the song is mapping. The sparse, slightly alien quality of the beat suggests that the emotional situation in the lyrics is not comfortable or familiar. Trying again, returning to something that didn't connect the first time, requires a particular kind of courage that the production's slightly unsettled sonic landscape mirrors with precision.
The Song as R&B Innovation
Reaching number one on the Hot 100 on June 17, 2000, and spending 32 weeks on the chart, "Try Again" represents the moment when Timbaland's sonic innovations became fully and undeniably mainstream without losing any of their experimental edge or their forward-looking quality. The song proved convincingly that the American audience for R&B radio was genuinely ready for something different from the production conventions of the era, that the appetite for innovation was larger than the industry's caution had assumed. In that sense its chart success is itself a kind of cultural statement about what listeners were actually ready for.
Persistence and Its Resonance
The theme of trying again speaks to something fundamental in human experience, which accounts for the song's sustained relevance across decades and demographic groups. Relationships that require effort, connections that take time to form properly, ambitions that demand repeated attempts before they yield: these are not experiences limited to any particular era or audience. 156 million YouTube views suggest that "Try Again" has found new audiences consistently since its release, each generation discovering in its elegant simplicity something that applies to their own specific version of not giving up on something worth having. Aaliyah delivered that message at the peak of her powers. The message is still being received and still being passed forward.
→ More from the 2000s File
View all 2000s hits →
Keep digging