You know that feeling when you see something from twenty years ago and it doesn't look "old," it just looks cool? That is the Aaliyah Try Again video in a nutshell. Honestly, if you dropped this visual on YouTube today for the first time, it would still trend within the hour. It’s got this weird, slick, industrial vibe that basically defined the start of the 2000s, and somehow, it hasn't aged a day.
Most people remember the song—that stuttering, glitchy Timbaland beat that literally changed how radio sounded. But the video? That was something else. It wasn't just a promo for a soundtrack; it was the moment Aaliyah transitioned from the "Princess of R&B" to a full-blown global icon.
The Mirror Room and That Hallway
Directed by Wayne Isham, the video kicks off in this trippy, darkened hall of mirrors. You've got Jet Li—Aaliyah’s co-star from Romeo Must Die—walking through like he’s in a high-stakes spy thriller. It's moody. It’s dark. It feels expensive.
The whole concept was to bridge the gap between the movie’s martial arts themes and the futuristic sound of the track. Timbaland is lurking in the shadows, beatboxing against the glass, and then Aaliyah appears. She’s not just "performing." She’s commanding the space.
There’s this specific technical detail that gets overlooked: the use of wirework. Because she had spent so much time training for her role in Romeo Must Die, she was actually a master of those Hong Kong-style stunts. In the video, she literally walks up a wall. No big deal, right? Except she makes it look like she’s just strolling down the street. It’s that effortless cool that nobody has quite been able to replicate since.
Why the Fashion Is Still All Over Your Feed
If you look at Pinterest or "Y2K fashion" mood boards today, you are going to see that crystal bra. Period.
Derek Lee, her longtime stylist, really outdid himself here. He basically grabbed a Dolce & Gabbana crystal-encrusted bra top and paired it with low-rise leather pants and a matching choker. It was a huge departure from the oversized Tommy Hilfiger and baggy jeans she was known for in the mid-90s.
✨ Don't miss: Why The Prince of Egypt is Still the Greatest Animated Movie Ever Made
Fun fact for the real nerds: the crystal bra actually offered so little coverage that they had to have a seamstress add extra rows of rhinestones at the last minute so she’d feel comfortable dancing in it. It worked. It became one of the most imitated looks in music history. You’ve seen everyone from Kim Kardashian to Normani pay homage to it because it’s basically the blueprint for "Space-Age Siren."
The Fatima Robinson Magic
You can’t talk about the Aaliyah Try Again video without mentioning Fatima Robinson. She’s the legendary choreographer who worked with Aaliyah on almost everything. The movement in "Try Again" is interesting because it’s not "busy."
It’s smooth.
It’s liquid.
It’s precise.
Instead of the hyper-energetic "booty shaking" that was starting to dominate music videos at the time, Fatima leaned into martial arts-inspired shapes. The hand movements, the way Aaliyah uses the cane at the very end—it all feels very deliberate. It was a nod to Black Greek fraternity step shows, which added this layer of cultural depth that most pop videos just don't have.
A Technical "Mistake" That Became History
While we’re talking about the video, we have to talk about how the song itself almost didn’t happen. Timbaland recently admitted that the main synth riff—that "wrr-wrr" sound—was actually a total mistake. He was just playing around with a keyboard and hit a weird rhythm by accident.
His engineer, Jimmy Douglass, caught it on the fly and told him to keep it.
Static Major wrote the lyrics.
Aaliyah recorded it.
The rest is history. It became the first song to reach number one on the Billboard Hot 100 based solely on radio airplay, without a physical single being released yet. That was unheard of back then. The video was the engine that drove that success, playing on a constant loop on MTV’s TRL and BET’s 106 & Park.
The Jet Li Cameo
It’s kinda wild to think about now, but having a martial arts legend like Jet Li in an R&B video was a massive crossover moment. He wasn’t just standing there; the video treated him like a co-star. The shadowboxing scenes in the mirrors mirrored the action of the film they were promoting, but it also made the video feel more like a short film than a commercial.
Why We Are Still Talking About It
Usually, music videos are disposable. They’re meant to sell a record and then fade away. But "Try Again" is a timestamp of a very specific era where R&B was becoming experimental. It was the "Matrix" era of music.
Aaliyah was only 21 when this came out. She won two MTV VMAs for it in 2000: Best Female Video and Best Video from a Film. When she accepted the award, she was already filming Queen of the Damned in Australia. She was at the absolute peak of her powers, and this video captures that lightning-in-a-bottle energy perfectly.
🔗 Read more: How He Loves Us: The Messy History of a Modern Worship Classic
If you want to really appreciate the craft of that era, go back and watch the 4K remasters or even the old behind-the-scenes "Making the Video" clips. You’ll see a young woman who was intensely involved in every frame, every outfit choice, and every eight-count of the dance.
Next Steps for the Super-Fan:
- Study the Choreography: If you’re a dancer, look for the "Try Again" breakdown on YouTube. The "cane" sequence at the end is a masterclass in prop work.
- Track the Evolution: Watch "One in a Million" and then "Try Again" back-to-back. You can see the exact moment she shifts from a teen star to a global force.
- Check the Credits: Look into the work of Wayne Isham and Fatima Robinson—they shaped the visual language of the entire early 2000s.