Remembering the Princess of R&B: 20 of Aaliyah’s best pop culture moments ever

The late R&B icon left us too soon but served up countless iconic moments. Two decades since her tragic death, let's celebrate her stunning legacy

Since the release of her breakthrough track ‘One In A Million’ in 1996, Aaliyah has held a place as one of pop’s biggest icons. In the years since her untimely death in a plane crash at 22, her legacy has only grown. Before her sudden passing, the Princess of R&B was making all the right moves. As the 20th anniversary of her death soon upon us (on August 20), and as her classic debut album ‘One In A Million’ finally arrives on streaming services today (August 20), we explore some of the star’s best pop culture moments.

Reaching for the stars

At just 10 years old, Aaliyah made her debut on TV singing ‘My Funny Valentine’, from the musical Babes In Arms, on the popular child’s talent show Star Search. Of course, Aaliyah wowed the crowd with her stunning vocals, but unfortunately the young star didn’t win. But she was still very chipper about her performance: “It was an incredible experience – me and [Ed] McMahon and just being on the Star Search stage because it was a show that I really looked up to.”

Romeo Must Die

As a multi-hyphenate of the ‘90s, Aaliyah did it all – she was a singer, fashion icon, model and had her own makeup line. In 2000’s Romeo Must Die, she added another string to her bow as an actor. The film was meant to incorporate elements of popular Hong Kong martial arts movies like Enter The Dragon into a modern American crime film. Although that concept didn’t quite come to fruition, Romeo Must Die will live on as Aaliyah’s acting debut and the reason she created her most popular track of all-time, ‘Try Again’. Speaking of which…

‘Try Again’

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Aaliyah’s stellar discography helped catapult Missy Elliott and Timbaland to producer stardom, and ‘Try Again’ was the song that truly made the latter rap’s go-to beat creator for years to come. With its fuzzy chords in the background doing their thing while the bassline zips around, ‘Try Again’ has stood the test of time not only because of how great it sounds, but also because of its music video, which quickly became a classic. In it, Aaliyah wore one of her most iconic outfits: the glittery bra with a matching choker. The look has been adopted so much for Halloween that you can even find specific costumes recreating the ‘Try Again’ ‘fit online. A ton of celebrities have recreated it themselves – like Kim Kardashian, who got some backlash for donning a similar outfit in 2017.

The 1996 Tommy Hilfiger campaign

Before she gave the world her most recognisable look, Aaliyah was known for wearing oversized menswear, and international fashion brand Tommy Hilfiger took their chance to capitalise on that. The brand styled the then-teenager in oversized jeans, men’s boxers, and bold logo-ed tube tops, and Aaliyah made Tommy Hilfiger cool for the girls while furthering the brand’s status in hip-hop alongside the likes of Fubu and Rocawear. To this day, when you see a woman rocking Tommy Hilfiger – especially a celeb – it immediately recalls the famous campaign Aaliyah did in the ‘90s.

When she looked just like Veronica Lake

Coming onto the music scene as a laid-back tomboy, Aaliyah often wore headscarves and bandanas with dark shades. Towards the end of her career, though, she took off those accessories and reinvented her aesthetic. After the whole girl-next-door look that she stuck with for some time, she came out with her iconic side fringe that was adopted by the likes of Rihanna and more later on in the ‘00s. Her hair always covered her left eye in homage to her favourite mid-century film star Veronica Lake — not Lisa “Left Eye” Lopes, as many might mistakenly think. After her death, the side swoop became a staple hairstyle of the ‘00s and still lives on today.

‘Are You That Somebody?’

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Although she never released the song on any albums of her own – it instead featured on the soundtrack for the Eddie Murphy remake of Dr. Dolittle – ‘Are You That Somebody?’ pushed the boundaries when it came to dance breaks in music videos. Until that time, dance breaks were usually reserved for boybands like *NSync and the Backstreet Boys, but Aaliyah claimed it for R&B stars too. ‘Are You That Somebody?’ truly solidified the star as a dazzling talent to watch. The song also gave us a return of the dream pairing of her and Timbaland, encompassing everything we loved about both of them — Aaliyah’s soprano vocals and Timbaland’s idiosyncratic production style — and earning the duo their first Grammy nomination.

Snaking around

Aaliyah has so many monumental music videos, including the one for ‘One In A Million’ which is her most iconic single. From the snakes to the infamous car shot of her laying on the back of a Ford Mustang and and the cameos made by other Blackground Records (was record label, which owned by her uncle Barry Hankerson) signees, it is a culture capsule of just how great the fashion, musicians, and themes of ‘90s R&B culture were.

Her award-winning

Aaliyah had (shockingly) only won two awards before she passed, and they were both for her being the visual trendsetter she was. In 2000, the then 21-year-old won two MTV Video Music Awards for Best Female and Best Video all for the aforementioned, record-breaking single ‘Try Again’. These two awards further prove just how much of a visual genius Aaliyah was as well as a musical one. Her makeup artist Eric Ferrel and various stylists created timeless looks to pop in front of the extravagant backdrops of perfect videos directed by legendary music video-turn-film director Hype Williams.

Singing for royalty

In 1998, Aaliyah was up for an Academy Award for Best Original Song – but she sadly didn’t win. The popular remake of the film Anastasia had been released with a beautiful, serene soundtrack, including a track from the pop princess herself: ‘Journey To The Past’. Since she was a nominee, the Academy asked the then 19-year-old Aaliyah to perform the stunning ballad at the 70th Academy Awards ceremony. This made Aaliyah the youngest performer at the Oscars until Billie Eilish did it in February 2020, aged 18.

Rocking the boat

The ‘Rock The Boat’ music video has become a part of one of the many conspiracies surrounding Aaliyah, with it being her last music video made before her death.  However, it is actually another record-breaking music video for the pop princess. With a fluttery island vibe, the posthumously released music video shows the young 22-year-old dancing near the seas in the Caribbean. Only weeks after her death, the music video was plastered on BET’s behind-the-scenes music show Access Granted, breaking the record for the most views the show had ever had.

That cover of Elle magazine

The August 1999 issue of Elle is cherished in the hearts of many fans of ’90s hip-hop. Thanks to that edition of the magazine, we got to see Aaliyah giggling side-by-side with a few of her sisters in music. Appearing on the cover with her longtime friend and labelmate Missy Elliott – as well as two of the most prolific female rappers of the time, Lil Kim and Da Brat – this issue of Elle immortalised the greatness of not only our favourite R&B star of the ‘90s, but also the golden age of hip-hop’s female empowerment moment.

Those iconic snaps of her with Damon Dash and Jay-Z

Before her untimely death, Aaliyah was reportedly “thinking of marrying” the hot-head Roc-A-Fella co-founder Damon Dash, At the time, Dash was managing the hottest rapper in the world in Jay-Z, while becoming the most revered music industry man out there. So, with her boyfriend being Jay’s manager, Aaliyah was great friends with today’s rap billionaire. Even Damon said Jay-Z tried hard to get Aaliyah to be his love, but Dash won her heart. And the pictures taken of Aaliyah and her Roc-A-Fella babe, as well as with the main man Jay, have become iconic themselves.

Ghetto Goth meets industrial rock

In an interview with MTV while on a press run for her film debut, Aaliyah dropped the bomb that she “loves rock” and wanted to dabble in it too. (Remember: this was before the internet broke down genre boundaries.) And who better to explore rock with than Nine Inch Nails frontman Trent Reznor? Aaliyah said they’d “met at the MTV VMA Awards and talked for a while and have talked on the phone a few times.” She added: “He’s a really nice person and extremely talented, so maybe we’ll be able to collaborate. I think our sounds would really mesh well, so I’ll bring a little something to the table, he’ll bring something, and we’ll see how it works.” Unfortunately, this never came to fruition, and we can only imagine what might have.

Queen of the Damned

This 2002 flick wasn’t the greatest movie ever made, but Aaliyah, as ancestral vampire Akasha, lifted its gothic horror to new heights with star power alone. Yes: she really got her teeth into the role.

Being interviewed by Beyoncé at the MTV Movie Awards 2000

Many Beyoncé and Aaliyah fans see this interview, which resurfaced on Twitter last year,  as a passing of the torch between the then-Queen of Pop to our current Queen Bey. At the time, Beyoncé was branching away from her other Destiny’s Child stars to make a name for herself as a solo artist, three years she paraded into our lives with ‘Crazy In Love’. This interview is still one for the history books, no matter how short and spontaneous it might have been.

A most modern kerfuffle

This pop culture moment came from beyond the grave. In 2013, when he was a middling rapper on his way to superstardom, Drake wanted to take Aaliyah’s unreleased tracks and compile a brand new record for the deceased star. But, of course, when you’re tampering with the Princess of R&B’s music, her fans are going to enter into a frenzy. This was also around the time when Chris Brown had used never-heard-before vocals from Aaliyah for the underperforming ‘Don’t Think They Know’. Although both thought they were paying homage to a legend, it caused a kerfuffle because fans claimed they’d taken her rough leftovers and used them for their own personal gains. Chris Brown managed to release ‘Don’t Think They Know’, but good thing Timbaland talked Drake out of his project.

Performing alongside Gladys Knight at only 11

A famous entertainment lawyer and manager, Hankerson was also married to the soul icon Gladys Knight, and he used that connection to help further his niece’s professional path. As well as making pop-up performances on Star Search when she was nine, the future R&B icon also performed with her celebrated step-aunt for five nights in Las Vegas at the age of 11. Regardless of where the opportunity came from, that’s not a bad start.

From one video star to another 

In 2019, Aaliyah’s best friend and industry superstar Missy Elliott was honoured for her innovation when it comes to music videos. At the MTV VMA Awards that year, Cardi B awarded her with the Video Vanguard Award, which is the highest award you could possibly get. However, when accepting her award, the moment was quite bittersweet, considering her biggest inspiration, Aaliyah, wasn’t there to celebrate the honour with her. This teary and heartfelt moment was beautiful to watch.

Aaliyah

The star’s third and final studio album, release just over a month before her death, secured her legacy, becoming one of the biggest and most influential R&B records ever, shifting more than 13 million copies. All of her records were amazing, of course, and here was her crowning glory.

And now her music can be heard all over the world

You can already hear the majority of Aaliyah’s singles on the web, bie it through YouTube or compilation albums that managed to get the rights to her huge hits. But most of her discography has remained in physical copies – until now. 20 years after her tragic death, the whole world can finally listen to her second body of work ‘One In A Million’; the very album that catapulted the start from a teen pop bopper to a fully-fledged star.

With the rest to follow, this is amazing news: Aaliyah’s music – which is what she devoted her life to – can finally get the recognition it deserves. All hail the Princess of R&B.

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