Home Music 5 Insane Behind-the-Scenes Facts About Aaliyah’s ‘Try Again’ That Will Blow Your Mind

5 Insane Behind-the-Scenes Facts About Aaliyah’s ‘Try Again’ That Will Blow Your Mind

by Zaria Davis
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Exactly 25 years ago, on March 21, 2000, the world was forever changed when Aaliyah unleashed Try Again, a track that didn’t just top charts. It rewired the entire soundscape of R&B, hip-hop, and pop, solidifying her place as an untouchable force in music history.

The song wasn’t merely a radio hit. It was an atmospheric, futuristic anthem that broke records, bent genres, and introduced the world to an unstoppable, visionary Aaliyah who was light-years ahead of her peers.

Today, to honor its silver anniversary, we are cracking open five jaw-dropping, rarely-discussed facts about this classic. Get ready. These are the stories behind the song that prove Aaliyah was truly one in a million.


1. The Beat That Changed the Game Was an Accident

Let’s start with the bombshell. One of the most iconic beats in pop culture history almost didn’t exist. The glitchy, hypnotic, ahead-of-its-time rhythm on Try Again wasn’t meticulously planned by Timbaland. It was born out of pure, happy chaos.

Timbaland admitted that while he was casually experimenting with a keyboard in the studio, he stumbled upon an offbeat sound that immediately caught the ear of engineer Jimmy Douglass. It was an accident. A beautiful, unpredictable accident. Douglass told Timbaland to stop and replay the strange loop. That quirky mistake ended up being the very foundation of the entire track.

Yes, the very DNA of Try Again came from a random keyboard slip-up. Proof that sometimes, history is made when you least expect it.


2. Billboard Had No Choice But To Bow Down

Here’s the fact that still leaves people shook two decades later. Try Again became the first song in Billboard Hot 100 history to reach number one based entirely on radio airplay. No CD singles, no physical sales, no downloads. This was before Spotify, before iTunes dominance, before YouTube streams.

People weren’t buying Try Again. They didn’t have to. Radio stations simply could not stop spinning it. The demand was deafening. Aaliyah’s voice was everywhere, from car stereos to corner stores to club speakers. It forced Billboard to confront a new reality. Airplay alone was enough to make a song number one.

Aaliyah did not need sales figures. She had cultural dominance, and the charts bent to her will.


3. The Original Lyrics Had Zero To Do With Love

Everyone associates Try Again with romantic persistence, thanks to its legendary hook. But what if I told you that wasn’t the original plan?

Timbaland and the production team originally crafted Try Again as a self-help empowerment anthem, encouraging people to get back up when life knocked them down. It was more motivational speech than love story. However, when the song was selected to appear in Aaliyah’s film Romeo Must Die, Hollywood executives pushed for lyrical adjustments to fit the film’s romantic subplot.

The bones of the track remained, but the verses were subtly rewritten to reflect themes of love and seduction. What we now hear as a sultry ballad was once meant to be a universal call for resilience.

Aaliyah could’ve been giving you self-improvement realness. Instead, she gave you both.


4. The Crystal Bra Look Cost Thousands

Let’s talk fashion. The Try Again music video, directed by Wayne Isham, is remembered for its slick, futuristic aesthetic. But the real showstopper? Aaliyah’s shimmering, jaw-dropping crystal bra top and matching choker.

That custom piece was not some off-the-rack accessory. It was a hand-selected Dolce & Gabbana masterpiece, sourced by her stylist Derek Lee to level up her signature streetwear look. The outfit merged baggy pants, metallic shine, and red-hot glamour into something instantly iconic.

Reports suggest that ensemble cost thousands. But no price tag could ever measure up to the cultural currency Aaliyah created by wearing it.


5. A Million-Dollar Video Inspired by Bruce Lee

The production of the Try Again video was nothing short of legendary. Behind the scenes, Isham and Aaliyah collaborated on a concept inspired directly by Bruce Lee’s classic film Enter the Dragon. You remember the hall of mirrors? That wasn’t a coincidence.

The entire video was an ode to martial arts cinema, fused with cyberpunk aesthetics and cutting-edge choreography. Executing that vision didn’t come cheap. The budget ballooned to a reported $1 million, an astronomical sum for the year 2000.

Aaliyah’s co-star Jet Li visited the set during filming and was blown away by her precise, high-energy performance. Watching the video, it’s easy to see why. Aaliyah moved like a warrior, a dancer, and a goddess all at once.

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Aaliyah’s Legacy: Still Untouchable

Twenty-five years later, Try Again stands as a masterclass in innovation, artistry, and sheer cultural impact. Aaliyah didn’t just release a hit song. She changed the entire landscape — from how music was charted to how music videos were conceptualized to how style itself was defined.

Every element of Try Again, from accidental beats to million-dollar visuals, was a testament to her visionary brilliance. No gimmicks. No fluff. Just timeless influence.

She told us, “If at first you don’t succeed, dust yourself off and try again.” But truthfully? Aaliyah never needed a second try.


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