On Aug. 25, 2001, the music world found out the shattering news that Aaliyah, one of the brightest still-rising stars of the past decade of popular music, had died in a plane crash in the Bahamas. The public grief following the news sent her then-recently released self-titled third album — soon to be acclaimed as her masterpiece, and one of the century’s most essential R&B releases — to No. 1 of the Billboard 200 albums chart. In the 20 years since, Aaliyah has remained at the top of mind for further generations of music fans, critics and artists, as one of the most beloved artists of her generation.
Below, Billboard staffers share their thoughts and memories of the Princess of R&B — the impact that she left, the influence she still carries, and the way her songs endure to this day.
Which Aaliyah song do you remember being the first that really made an impression on you? What about it really caught your attention?
Katie Atkinson: Definitely “Are You That Somebody?” The very first thing I noticed was the baby crying and, like a lot of genius musical choices, I thought it was beyond weird at the time — but 20-plus years of Timbaland music later, it all makes sense. The music video made a big impression on me too, because of Aaliyah’s perfect style (no one combined the masculine and feminine better) and the choreography that I thought I could copy but never really came close.
Carl Lamarre: The first few songs that I loved from Aaliyah were probably the ones that lived on movie soundtracks, including “Are You That Somebody?” (1998’s Dr. Dolittle), “I Don’t Wanna” (1999’s Next Friday), along with “Try Again,” and “Come Back in One Piece” (2000’s Romeo Must Die). The one track that gravitated to me the most when I got older was “At Your Best (You Are Love).” I began understanding relationships, despite being a novice in that department. I wanted to cling to that same feeling she sang about so much that I played the song repeatedly while trying to fall asleep.
Jason Lipshutz: In the summer of 1998, Dr. Dolittle with Eddie Murphy was a very big deal if you were around the age of 10, and “Are You That Somebody?” was everywhere leading up to the movie before being featured within it. I remember watching the video for the brief shots of Murphy interacting with wacky talking animals… and then eventually watching it because the song itself ruled. I hadn’t been familiar with Aaliyah’s first two albums at that point, but “Are You That Somebody?” unlocked her as a rising pop figure for me, and I paid close attention to her following singles (and eventually went back to those first two albums).
Heran Mamo: Her cover of The Isley Brothers’ “At Your Best (You Are Love)” is so painstakingly beautiful, and her airy, a cappella “Let me know, let me know” coos take my beath away every time. With Drake and Frank Ocean respectively sampling and covering her twinkling version, among many other household R&B and hip-hop artists, Aaliyah was the positive, motivating force behind “At Your Best (You Are Love)” becoming a timeless, generation-spanning record.
Neena Rouhani: Aaliyah and I are both from Detroit, so her music was constantly spun on the R&B and hip-hop stations in the city my entire life. The track that gave me chills, even as a five-year-old in the back of my mom’s ‘99 Honda Civic, is “Are You That Somebody?” My mom used to call it “the song with the crying baby,” which to me speaks to just how iconic that Timbaland beat is. I later learned that the track was made in four hours flat, further cementing it as a classic in my eyes. Aaliyah’s melodies, vocal stacking, arrangement, all of it felt so ahead of its time. She was truly an original and “Are You That Somebody?” was a testament to that.
Andrew Unterberger: The first song of hers I loved was definitely “If Your Girl Only Knew,” with its casually flippant cool and brain-bending bass line. But the real lightning bolt was “One in a Million,” the MTV-conquering slow song built on minimal drums, cricket chirps (?) and Aaliyah’s disarmingly intimate vocals, lushly layered on the chorus and piercingly vulnerable on the bridge. I was still easily scandalized by overtly sexual songs at 10 years old, but this one was just innocent and emotional enough in its sensuality that it didn’t feel totally beyond my grasp — it just gave me, well, a really good feeling.
More than maybe any other pop star of her era, Aaliyah had a kind of mystique around her — one that made her seem both approachable and otherworldly at the same time. What was it about her persona, do you think, that made her stand out as such a singular presence at the time?
Katie Atkinson: I didn’t feel like I knew her like I did with Britney or Christina or other contemporary pop stars, but maybe that’s because of her introduction. Instead of seeing clips of tween Aaliyah on the Mickey Mouse Club with a bunch of future superstars, aside from one Star Search appearance as a 10-year-old, music fans saw her arriving at age 15 as a fully formed artist. We didn’t really see the origin story as much, so she remained an enigma.
Carl Lamarre: You never got the full scope of her. That was the gift and the curse of her mysterious aura. She gave you just enough for you to ponder on before diving back into reclusive mode. But when she was willing to shed those layers, boy, we were in for a treat. I still believe the final album Aaliyah was her breakthrough in that area and would have been the start of something special. She fully began realizing herself as a woman and who she was ultimately becoming.
Jason Lipshutz: Something about Aaliyah’s vocal affectation helped her strike that balance, an ethereal quality that she knew how to apply both to yearning verses and accessible choruses. She sounded perpetually invested in her craft but also valuing mystery, as if she understood how to immerse herself into popular R&B without giving too much of herself away to the general public. That’s a line that only a select few artists have ever been able to successfully walk, but I’d count Aaliyah among them.
Heran Mamo: Her charisma. Her side-swept bangs and sweet soprano voice gave Aaliyah the girl-next-door innocence while her era-defining street style gave her an enviable edge, validating the “Are You That Somebody?” line about the juxtaposition of her personality, “Sometimes I’m goody-goody/ Right now, I’m naughty naughty.”
Neena Rouhani: Aaliyah was inexplicably irresistible. She could place you in a trance with what seemed like little to no effort, which I think was the beauty of her persona. It felt so authentic, so entirely her own. She was just balanced in a way that I don’t know if anyone else has achieved, though they’ve tried. She was feminine yet edgy, unattainable yet relatable, graceful yet tough. She served as a bridge between so many qualities that are often divided and contrasted, which is why you had to love her.
Andrew Unterberger: I think it was that combination of musical intimacy — her songs just felt close, in a way few R&B artists of her era managed or even attempted — and personal distance, where she was always kept somewhat at a remove in her videos and appearances, almost hidden behind sunglasses and eyepatches and her own hair. And there also just seemed to be a general kindness to her, a gentleness and a humility that made her sound friendly and warm even when she was singing kiss-off songs. From stories you heard at the time and after the fact, it seems like nearly every man she ever met fell in love with her — so clearly the impression was genuine.
Aaliyah was a striking and influential presence in the world of fashion as well as music. When you think of Aaliyah, which look of hers appears most immediately in your mind’s eye?
Katie Atkinson: All of the looks from the “Are You That Somebody?” video. To me, she’s permanently in those half-pigtails with swooped bangs wearing baggy pants and a midriff-baring top.
Carl Lamarre: Of course, there were a few things: The sunglasses look that Aaliyah mastered at the early stages of her career. Then, I always return to her wearing the Tommy Hilfiger crop top or the Brick Layers jersey she wore at the 1996 MTV Rock N’ Jock Celebrity Basketball Game as unique, eye-popping looks for me. Those were iconic looks that still receive the Halloween treatment when it comes to costumes.
Jason Lipshutz: When I think of Aaliyah, I think of Aaliyah – the cover of her self-titled third LP, released just weeks before her death. In front of a red background, Aaliyah stands with her shirt clinging to her body and curls meeting her shoulders, her face and posture exhibiting boundless confidence. It’s a simple, elegant look that matches the straightforward statement of the album title and her final LP as a whole.
Heran Mamo: Without a doubt her head-to-toe Tommy Hilfiger look from the 1996 campaign that later served as key inspiration for the women’s line. Aaliyah effortlessly arrived in style at the intersection of baggy tomboy swagger and midriff-revealing sexiness with the logo-bearing bandeau, boxers and jeans set. And like every trend setter, she had millions flocking to her every Halloween with vintage copycat looks. Yara Shahidi even paid homage to Aaliyah’s Hilfiger look in an episode of grown-ish last year that was aptly titled “Age Ain’t Nothing But a Number.”
Neena Rouhani: This is so hard because there are so many, so I might cheat a little here. There was one outfit she wore to an MTV red carpet, which was this asymmetrical black leather spaghetti strap top paired with blue jeans and a bedazzled belt. I’ve always been obsessed with that outfit and I’d absolutely wear it today. My favorite music video look from her was when she had green makeup, blue-grey cargos, belly chain and that swoop in “Are You That Somebody?” That might be my halloween look this year. When it comes to her red carpet looks, that yellow and black Roberto Cavalli dress was untouchable.
Andrew Unterberger: Gotta be her with the swoop bangs and the bird in the “Are You That Somebody” video. It was probably a reference to the Dr. Dolittle soundtrack the song came from — as well as to Aaliyah’s opening line, “Boy, I’ve been watching you like a hawk in the sky” — but it also seemed totally normal that Aaliyah would be a natural born falconer, among her many other skills.
The film world also was beckoning to Aaliyah at the time of her death — she scored starring roles in Romeo Must Die and Queen of the Damned, and had countless hit videos from movie soundtracks. Do you think she would’ve become a true film star, or would it have ultimately taken a backseat to her music career?
Katie Atkinson: She could’ve done anything she wanted. When Aaliyah died, the tide was really turning from artists having to choose between music or acting to being able to dominate in both (see: Jennifer Lopez). So much of her appeal as a music star was her videos, so it was a natural progression for her to be onscreen.
Carl Lamarre: I believe she and Tupac would have been perennial film stars had their lives not been cut short. The potential was there, and she was beginning to find her groove. I still consider Romeo Must Die to be one of my favorite films. Her chemistry with martial arts pro Jet Li was perfect despite their differences in backgrounds.
Jason Lipshutz: It’s hard to say, since her roles in Romeo Must Die and Queen of the Damned suggested a true talent in front of the camera but one which was still raw considering her age and experience. Yet Aaliyah was signed on to star in the two Matrix sequels, the Sparkle remake and Honey prior to her death, so she certainly would have gotten a legitimate opportunity to become a big-screen star if that was the route she wanted to pursue.
Heran Mamo: She was destined to have a successful film career that complemented her musical career, because Aaliyah was the full package. The natural born leader not only had the regal titular role in Queen of the Damned, but she also co-produced the Top R&B/Hip-Hop Albums-topping soundtrack for the box office hit Romeo Must Die, which she provided four songs for (including her first and only Hot 100 No. 1 “Try Again”). Aaliyah could have had a similar trajectory as Jennifer Hudson or Mary J. Blige by balancing music and movies, vying for both Grammys and Oscars and extending the global reach of her undeniable on-screen charm while also flexing her producer muscles on more film soundtracks.
Andrew Unterberger: It’s a little tough to say, because neither of the two films she appeared in — Romeo or Queen — were particularly strong starring vehicles, and she had some particularly leaden co-leads to work with. But watching the more casual early scenes of Romeo, you do get that scene whenever Aaliyah’s around and interacting with her co-stars: There’s just something about her. That kind of undefinable magnetism is usually the most important ingredient in any recipe for film stardom, so I would’ve bet on her getting there sooner than later, particularly with some better movies.
Aaliyah’s catalogue was largely unavailable on services for the first decade of the streaming era — what kind of impact do you think that had on her legacy? Has it put a ceiling on her contemporary impact, or has her music’s scarcity just made it seem more sacred?
Katie Atkinson: It has to have had a huge impact on new fans being able to find her. Of course, you can always find the music you’re looking for somewhere, but potential Aaliyah fans are missing out on that passive discovery that a streaming playlist provides. I should hope the now-parents or cool aunts and uncles are pointing young music fans in the right direction, but her catalog finally making its way to streaming will allow for people to stumble on her genius accidentally.
Carl Lamarre: I’m leaning on the latter mainly because it goes back to her mystique. It further heightened the mystery of her legacy, especially for a younger generation yearning to understand the brilliance and reverence behind her catalog.
Jason Lipshutz: As streaming has become ubiquitous, catalogs that are not easily available have become a rarity — a frustration for those who cannot easily press play on their favorite artists, but a special occasion when those projects do eventually arrive on streaming platforms, as One in a Million did last week. It’s impossible to say how much Aaliyah’s catalog being off of streaming platforms has either hurt her legacy or contributed to her aura, but now that One in a Million is widely available, hopefully a ton of unfamiliar listeners can stumble into its greatness head-first.
Heran Mamo: Access to Aaliyah’s music was enshrined prior to its historical arrival on streaming services. Unlike last year’s vinyl boom, owning a physical copy of Aaliyah’s music wasn’t just “cool” or “vintage” — it was quintessential for consumption. The palpable records, CDs and cassette tapes made her fans feel that much closer to Baby Girl, holding onto her legacy for an eternity that’s heard in her music. That intimacy won’t die out once her discography is fully made available for streaming: It will distinguish the OGs from the newbies, the younger generation of R&B and hip-hop lovers who are around the same age as Aaliyah at the time of her death and can freely comb through her catalog and shuffle it amongst their favorite artists, who probably directly or indirectly introduced this group of listeners to Aaliyah because of her influence.
Neena Rouhani: I certainly don’t think it stifled her influence in the R&B/hip-hop world. People really clung onto the music of hers that they had access to over the last two decades. And even beyond the music, her persona and style are evident in so many celebrities that came after her. It proves that the stop on her music didn’t prevent the masses from being influenced by her in other ways. It was sad, to say the least, that many of us grew up without ever hearing most of her deep cuts. It would’ve been nice to see a ’90s Aaliyah track go viral more easily on TikTok, but luckily that can happen now.
Andrew Unterberger: It is kind of fitting that Aaliyah, unknowable superstar, would be the one iconic pop artist still missing from streaming services all these years later, isn’t it? I think it definitely helped with the aura of these songs to be kept off streaming — it’s hard for songs to retain their mystery after being cycled through a million throwback and workout playlists — but it also helps their impact now for them to finally be joining the party, giving fans specific occasion to celebrate her all over again and probably enticing a share of new listeners in the process.
Aaliyah’s music was often cited as being ahead of its time — to the point where 20-30 years later, we still might not have totally caught up. What song of hers still sounds the most like the future to you?
Katie Atkinson: I think it’s a tie for me between two Timbaland productions on her final album: “More Than a Woman” and “We Need a Resolution.” The syncopated beats with their unexpected little sonic flourishes throughout are still jarring 20 years later, but the most impressive part is how Aaliyah’s voice manages to cut through the glitch to steal the focus of each song. Anyone else singing along to these beats could easily get swallowed up by them.
Carl Lamarre: I remember watching “More Than a Woman” as a 12-year-old and thinking she was way ahead of the curve with that video. I sonically believe that song and “Try Again” were also beyond our time. I think they would have had the same flair and pop as they did over 20 years ago.
Jason Lipshutz: When it came out, “Are You That Somebody?” sounded like the future of popular R&B… and nearly a quarter-century later, it still sounds remarkably fresh, a vision of pop too cool to fully comprehend in one listen. Part of that has to be credited to Timbaland’s production, which would later inform so much of popular music, but Aaliyah’s ability to synthesize that sonic bed and create her own vision turned “Are You That Somebody?” from a cool beat into a classic.
Heran Mamo: “Are You That Somebody?” has gone down in history as one of Aaliyah’s most forward-thinking hits. From Timbaland’s beat-boxing ad-libs and twitchy drum programming to the infamous sample of a baby cooing to Aaliyah’s swift then stretched out vocals, the R&B-meets-avant-funk track walked so Destiny’s Child and later Beyoncé on her own could run. While love and breakup songs are hardly original concepts, Aaliyah’s songs became an exception to the rule by way of their production that virtually no one else had heard of before in the ‘90s but became all the rave on the mainstream charts in the ‘00s, ’10s and now the ‘20s.
Andrew Unterberger: There is no song from the 20th century I’m more sure would absolutely light the pop world (and the larger internet) on fire if released today than “Are You That Somebody.” Maybe some of Timbaland’s rap interstitials are showing their years by now, but everything also about the song — the beat, the melody, the lyrics, the structure, the video, those baby wails — is still mind-blowing. It’s one of the few ’90s songs for which there’s absolutely no contemporary analog.
Few artists from her era are as cited by current artists as an influence or inspiration — and perhaps fewer still are sampled, interpolated and covered as frequently. Do you think Aaliyah is the most important R&B artist of the last 25 years?
Katie Atkinson: I think the answer to this question has to be yes, because if you look at other potential options — Beyoncé, namely — you have to wonder whether Bey or Destiny’s Child would have even existed if it weren’t for Aaliyah’s influence. On top of that, Aaliyah wasn’t afforded the opportunity for her music to evolve alongside Beyoncé and other would-be contemporaries for the past two decades. When you realize her musical impact was made entirely over seven years, it just makes you wonder how much more she would have been capable of and just how much she accomplished in such a short time.
Carl Lamarre: You know what? When you sit back and think about it, there are so many reasons why she is. Artists a la Normani, Ciara, Tinashe, and Tink all share different entry starting points as R&B artists but maintained Aaliyah’s principles through music and choreography. Even from a sampling standpoint, Drake’s 2010 “Unforgettable” utilized “At Your Best,” while today’s R&B acts like Blxst (“Be Alone”) and Nija (“Ease My Mind”) recently tapped into the Aaliyah well and struck gold on their respective records. It’s incredible that despite her music not being on streaming services for so long, she still found a way to be a trailblazer for different generations in multiple genres.
Jason Lipshutz: It’s Aaliyah, Mary J. Blige and Usher in some order for me, as artists who could all utilize sky-high ambition to impact mainstream music, sell millions of albums while still telling very human stories. When we look back on the past quarter-century of R&B music, those names are all indispensable.
Heran Mamo: Yes, and the 325 Aaliyah samples according to WhoSampled are numerical proof of that. Lyrically and melodically embedded in the DNA of modern R&B/hip-hop is Aaliyah’s supple soprano vocals, Timbaland and Missy Elliott’s signature bouncy, rhythmic production and the late Static Major’s emotion-saturated songwriting.
Andrew Unterberger: Plenty of artists have a claim — Mary J. Blige, D’Angelo, Usher, maybe TLC if you want to stretch the timeline a bit — but Aaliyah remains the absolute gold standard. She’s perhaps the biggest reason why you no longer have to be a powerhouse belter to be an R&B superstar: You just have to be melodic, thoughtful, and make people want to know more about you. Outside of perhaps the boys in Silk Sonic, you’d be hard pressed to find a major figure in R&B from the past 10 years who you couldn’t trace back to Aaliyah in some way — and there’s little indication of that changing anytime over the next 10, either.
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