In The Number Ones, I’m reviewing every single #1 single in the history of the Billboard Hot 100, starting with the chart’s beginning, in 1958, and working my way up into the present.
The coolest person in the world. In the last few years of her way-too-short life, that was Aaliyah. I can’t think of any other way to describe her. Aaliyah made futuristic brain-scramble music, and she did it on a huge stage, helping introduce wild and psychedelic new sounds to the mainstream. But Aaliyah never made a big deal about the way that she updated the pop-music vocabulary. Instead, she found ways to float effortlessly over non-Euclidian alien soundscapes, making them sound as natural as a shrug or a sigh.
Aaliyah could sing, and she could sing in ways that most of her ’90s R&B peers never even attempted. While the rest of the R&B landscape was locked in a melisma arms race, everyone competing to see who could sing the most notes, Aaliyah flattened her delivery out into a pillowy glide. There was never any sweat in her sound. Instead, her voice was an ethereal flicker that fully internalized the twists and turns of the strange new tracks that she chose.
Aaliyah had the best taste in collaborators. When Missy Elliott and Timbaland’s sci-fi space-bleeps first filtered into mainstream R&B, Aaliyah was the first major star to take notice, to build that approach into what she was already doing. Aaliyah was much, much younger than Missy or Tim, but she was also far more famous, and her embrace of those sounds is probably the single greatest factor in those sounds flourishing across the pop charts. As a musician, Aaliyah was hugely consequential. She could see the future, and she helped shape it, even though she’d never get a chance to live there.
Aaliyah’s cool went far beyond her power as a musician. She was beautiful enough to stop your heart, and she did interesting things with her beauty, carrying it with a sense of adventurous poise. The people who worked with Aaliyah have always remarked on her lack of ego, her collaborative verve. She seemed to enjoy her fame, even though she’d been exploited in every way that a person could be exploited. When Aaliyah died, she’d already left a deep impact on pop music, and she was standing on the precipice of movie stardom, too. There’s no telling what she could’ve become if she hadn’t boarded that overloaded plane in 2001.
In her brief recording career, Aaliyah left behind a generous handful of outright classics, songs that rewired the circuitry of popular music. In that time, though, Aaliyah only reached #1 on the Hot 100 once. That lone chart-topper isn’t necessarily Aaliyah’s best song, or her most revolutionary, even though it’s great. This column can’t hope to do more than hint at Aaliyah’s importance, but we can at least talk about how that #1 hit was a total banger.
Aaliyah Haughton was about my age, and that’s one of the many reasons that her death hit me hard. But I can’t claim that I ever identified with Aaliyah. She always seemed to belong to another reality — one more adult and sophisticated than anything I could imagine. In Aaliyah’s life, at least one shadowy force took advantage of that false sense of adulthood. When she got famous, though, Aaliyah was really just a kid.
Aaliyah Haughton was born in Brooklyn and mostly raised in Detroit. (The Bee Gees’ “Too Much Heaven” was the #1 song in America on the day of Aaliyah’s birth.) Aaliyah’s family had connections to the entertainment business; her uncle Barry Hankerson had once been married to former Number Ones artist Gladys Knight. Aaliyah’s mother sent her to singing lessons when she was a kid. Some nights, young Aaliyah would sing on the same stages as Gladys Knight. In 1989, a 10-year-old Aaliyah sang “My Funny Valentine” on Star Search, and she already seemed fully self-possessed. Like so many of her fellow future superstars, she didn’t win Star Search.
When Aaliyah was 12, her uncle Barry Hankerson launched his Blackground Entertainment label and signed a distribution deal with Jive Records. He signed Aaliyah almost immediately. At the time, Hankerson was R. Kelly’s manager, and he introduced a very young Aaliyah to Kelly. When she was 14, Aaliyah recorded her debut album Age Ain’t Nothing But A Number. Kelly produced the album, and he wrote almost every song. Given what we now know about R. Kelly, everything about that situation is absolutely horrific, right down to the album’s title. Kelly was all over the album’s lead single, the #5 hit “Back And Forth.” Kelly also produced Aaliyah’s cover of the Isley Brothers’ “At Your Best (You Are Love),” which made it to #6. (For obvious reasons, I’m not going to rate the Kelly productions or put the videos in this post. That Isleys cover is legit beautiful, though.)
R. Kelly was a huge part of Aaliyah’s whole public image at the beginning of her career. She was presented as Kelly’s protege and as a younger take on the Mary J. Blige archetype. She wore baggy clothes and kept her eyes hidden behind sunglasses, and she remained a figure of mystery and fascination. But while she radiated that cool, Aaliyah was also the victim of some serious crimes. R. Kelly secretly married Aaliyah in 1994, when she was 15. Kelly’s underlings had given her a fake birth certificate that claimed she was three years older. Later, Vibe published the marriage certificate, but Kelly and Aaliyah both denied the story. A few months later, Aaliyah’s family had the marriage annulled. Aaliyah never associated with Kelly again, and she never spoke of her relationship with him, either in public or private. I can’t even imagine what she went through.
After detaching herself from Kelly, Aaliyah moved from Jive to Atlantic, and she found some new collaborators. Timbaland and Missy Elliott were just starting to break through in the R&B world after working for Jodeci member Devante Swing’s Swing Mob label. Their sounds were wild and otherworldly, and Aaliyah understood them right away. Missy and Tim became Aaliyah’s main collaborators when she made her 1996 sophomore album One In A Million. They co-wrote lead single “If Your Girl Only Knew,” and Tim produced it. “If Your Girl Only Knew” is one of the funkiest, headiest hits of the ’90s, and it peaked at #11. (You ever heard the Rahzel human-beatbox version? It’s so good.)
Just like Aaliyah’s first album, One In A Million went double platinum. One In A Million also established that Timbaland and Missy Elliott’s way-out sound had serious commercial potential, and it helped introduce a whole new herky-jerk electronic take on R&B that marked a near-complete break from everything that had come before. But the biggest chart hit on One In A Million was one of the few songs that didn’t have Missy and Tim’s fingerprints. Aaliyah took the pretty-but-pedestrian Diane Warren ballad “The One I Gave My Heart To” to #9. (It’s a 6.)
Diane Warren-type ballads might’ve still ruled the charts in the mid-’90s, but Aaliyah wasn’t very interested in chasing that formula. Instead, she fully entrenched herself into Missy and Timbaland’s whole future-funk circle. Aaliyah appeared on tracks from Missy and from associated acts like Ginuwine and Playa. In 1998, Aaliyah teamed up with Timbaland for “Are You That Somebody?,” a track from the Dr. Doolittle soundtrack. “Are You That Somebody?” was never commercially released as a single, so it only made the Hot 100 at the very end of 1998, when Billboard changed its rules. By that point, “Are You That Somebody?” still got enough radio play that the song reached #21 on the Hot 100, but that doesn’t give any indication of its impact.
“Are You That Somebody?” was a seismic track, a pop game-changer. The song’s stop-start syncopation sounded like a transmission from another galaxy. Tim filled the track with strange effects, like sampled baby coos and mouth-clicks that went beyond human beatboxing, into proto-ASMR territory. Aaliyah just levitated over all of it, broadcasting an unflappable sense of ease. The song was everywhere, and it made the world feel like a cooler place to live in the summer of 1998. I think I’m still processing it.
I’ve got a book coming out later this year, and when I had to get an author photo taken, I got the idea into my head that I wanted to pose with a falcon. I had other ideas — a flaming sword, a non-Photoshopped explosion behind me –but the falcon was the one that really stuck. I researched falconries near me and everything, but virtually everyone in my life convinced me that I should let the idea go and take a normal picture instead. After I dropped falcon idea, I figured out where I’d gotten it. It was the “Are You That Somebody?” video.
After the twin triumphs of One In A Million and “Are You That Somebody?,” Aaliyah landed her first movie role. The big-deal producer Joel Silver was looking for a way to turn Jet Li, the great Chinese martial artist, into a Hollywood star. I was all about this. Jet Li was the man. By the time Li made his Hollywood debut as the villain in 1998’s Lethal Weapon 4, I was already a fan. Back when Hong Kong movies weren’t quite so easy to find in America, I’d rented a VHS copy of Fist Of Legend from my local Chinese grocery store. Jet Li was worth that extra effort. This guy moved like a liquid knife, and I couldn’t wait to see what he could do with a serious budget behind him. And you know what? He did pretty well! Li put in his best work in Asian movies, but he had a nice little run in Hollywood. The One? Unleashed? Motherfucking Cradle 2 The Grave? Good times at the movies. That run really started with Romeo Must Die.
I like Romeo Must Die. It’s a total Saturday-afternoon cable movie, not a canonical classic, but it’s fun. The story goes for a vague Shakespearean thing about a romance unfolding during a war between Black and Chinese gangs in Oakland. The romance itself isn’t really the point, though. Instead, it’s all goofy, energetic setpieces. The Polish cinematographer Andrzej Bartkowiak, making his directorial debut, established a cartoony, hyperactive style that he’d use on a few more action flicks. His next two movies, Exit Wounds and Cradle 2 The Grave, both starred DMX, who popped so hard in a tiny Romeo Must Die supporting role that he briefly became a bankable action star who could get his rap protege Drag-On cast in supporting roles.
Aaliyah is the romantic lead in Romeo Must Die, even though she and Jet Li have absolutely zero chemistry and never even kiss. I don’t even mind. That’s fine. Aaliyah still comes off as a total natural onscreen. She’s got charm and presence. She’s a movie star. When she was cast, part of the calculus was probably the idea that Aaliyah would be all over the soundtrack, that the soundtrack would help sell the movie. That’s what happened. Romeo Must Die was a solid hit, more than tripling its $25 million budget. The soundtrack album went platinum, and Aaliyah’s “Try Again” went all the way to #1.
Aaliyah served as executive producer on the Romeo Must Die soundtrack. She included four of her own songs, as well as tracks from friends and peers — Timbaland & Magoo, Ginuwine, Playa, Destiny’s Child. Lead single “Try Again” came from Timbaland and another of his regular collaborators, the Kentucky-born songwriter Stephen “Static Major” Garrett. Like Tim, Static had come up through Devante Swing’s Swing Mob camp. He’d co-written Tim’s first big hit, Ginuwine’s 1996 classic “Pony.” (“Pony” peaked at #6. It’s a 10.) Static also led Playa, an R&B trio that recorded one album for Def Jam. (Playa’s highest-charting single, the 1998 Timbaland production “Cheers 2 U,” peaked at #38. Static Major will eventually appear in this column — posthumously, as a guest singer. He died after suffering respiratory arrest in a Louisville hospital in 2008. He was 33.)
Static Major and Timbaland wrote “Try Again,” and Timbaland produced it. Static’s original lyrical idea was that “Try Again” should be about the importance of persistence. But Barry Hankerson, still managing Aaliyah, told him that it had to be a love song, so Static reworked the lyrics. You can kind of tell. The chorus, presumably unchanged, riffs on the old cliché about trying again if at first you don’t succeed. The verses make vague allusions to some kind of romantic situation, and they’re a little slapdash. Aaliyah still sells them. Her narrator is into somebody, but she’s not willing to give in to her feelings fully. She wants this other person to keep courting her, but she won’t commit to anything: “This ain’t a yes, this ain’t a no/ Just do your thing, we’ll see how we go.” Maybe she’s stringing this other person along. Maybe she just hasn’t made up her mind yet. Either way, it seems totally plausible that this other person would want to keep trying.
On a song like “Try Again,” though, the lyrics are entirely secondary. It’s the sound that hooks you. When Timbaland made the “Try Again” track, he was in a whole other zone, seemingly reinventing his style from one song to the next. On the “Try Again” intro, Tim lays out his intentions: “It’s been a long time; we shouldn’t have left you without a dope beat to step to.” With that line, Tim paraphrases something that rap god Rakim had said on Eric B. & Rakim’s 1987 single “I Know You Got Soul.” (Eric B. & Rakim’s only charting Hot 100 single, 1992’s “Juice (Know The Ledge),” peaked at #96. They also guested on Jody Watley’s 1989 hit “Friends,” which peaked at #9. That’s an 8.) With that quote, Timbaland paid tribute to a rap elder, and he also made sure to point out the dopeness of his own beat.
Tim actually hadn’t made anyone wait a long time without a dope beat to step to. He was making dope beats all the time in the late ’90s and early ’00s. But if Tim wanted to draw attention to what he’d done on “Try Again,” then fair enough. The “Try Again” beat is something special. It starts out with echoed-out hi-hats coming in from all sides, as extremely synthetic strings and horns recall the burnished-steel gleam of Brad Fiedel’s Terminator score. The drums come in from odd angles — some sounds seemingly played backwards, others hitting at irregular intervals. Tim layers his own murmured, echoing hypeman vocals all over the beat, making himself a part of his own textured track. When the beat kicks in, it’s driven by the same kind of wriggling 909 bassline that drove so many Detroit techno and acid house classics.
There are sonic ideas all over “Try Again”: ghostly wandering sitars, eerie synth whistles, Tim doing the “vicky-vicky” DJ-scratch imitation that he always loved so much. Given all that, you’d think that “Try Again” was a domineering dancefloor track, but that’s not really what it is. Instead, “Try Again” is all insinuating atmosphere. It winds and wafts its way through the air like incense smoke. Timbaland and Aaliyah’s vocals are narcotically understated. Aaliyah breezes through Tim’s sound effects. She’s an island of self-assurance in all that nervous rhythmic play. She’s fully locked in with Timbaland; I love the blithe ease of her “you don’t wanna throw it all away” bit.
The other night, I got high, threw “Try Again” on in my headphones, and took my dogs out for a walk. It might’ve been the highlight of my week. “Try Again” casts a spell. It wiggles and worms and darts and hiccups. Sometimes, the track sounds like it’s breathing, with all sorts of gasps and sighs from both Tim and Aaliyah showing up everywhere. But the groove never dominates the melody. Instead, melody and groove support each other, blurring into one another until it’s hard to tell where one ends and the other begins. “Try Again” doesn’t really have a bridge, and it repeats its chorus a whole lot of times. In most cases, that would come across as lazy songwriting. With “Try Again,” it’s different. Every new chorus repetition is just an invitation to bask in that sonic world for a few seconds longer. It’s a strange, striking, beautiful song. I loved it in 2000, and I love it now.
Wayne Isham, the veteran glam-rock director, made the “Try Again” video. Nothing much happens in the clip. There’s a room full of mirrors and floating platforms, and Jet Li and Aaliyah dance with each other via Hong Kong wire-work. But Aaliyah, rocking an extremely sparkly bra/choker situation, brings her strange angular star power to every frame she’s in. She’d come a long way from the baggy leather jeans and skullies that she’d been rocking a few years earlier. Here, her swagger comes across as pure glamor.
When “Try Again” reached #1, it became a significant pop-chart first. At the time, “Try Again” hadn’t come out commercially as a single. Billboard had always used a combination of single sales and airplay to figure out the Hot 100. Through most of the ’90s, the magazine wouldn’t list songs that weren’t available as singles. Even after that rule changed, songs that weren’t singles were at a distinct chart disadvantage. “Try Again” still broke through to become the first-ever airplay-only #1 hit. (After the song reached the top, Virgin pressed up a vinyl single.)
More importantly, though, “Try Again” is the first Timbaland production to reach #1. Tim had made plenty of hits, but his imitators, producers like Rodney Jerkins and Kevin “She’kspere” Briggs, had broken through on the Hot 100 first. (Those Timbaland ripoffs were mostly pretty great, too. That’s just how cool that sound was.) “Try Again” proved that Timbaland wasn’t just a sonic pioneer; he was also a guy capable of making the biggest song in the country. Timbaland will appear in this column again, both as producer and lead artist. But “Try Again” was the only #1 hit from Tim’s true heyday as both a craftsman and an experimentalist.
Aaliyah wouldn’t get a chance to repeat what she’d done with “Try Again.” After Romeo Must Die, she flew to Australia to film her second movie, the vampire flick Queen Of The Damned. While working on the movie, she also recorded her third album, the self-titled LP that came out in July 2001. As far as I’m concerned, that album is Aaliyah’s masterpiece. It’s even spacier and slinkier than her past records, and it sounds more grown, more confident. Timbaland only produced three of the tracks on Aaliyah, but the feeling of those Aaliyah/Tim collabs is all over the LP.
The first single from Aaliyah, the Timbaland collab “We Need A Resolution,” peaked at #59 — pretty sad, considering that it’s an amazing song. Second single “More Than A Woman” did better, reaching #25. By the time that happened, though, Aaliyah was no longer with us. In August 2001, Aaliyah flew to the Bahamas to film her “Rock The Boat” video with director Hype Williams. When she flew back to Florida, the small private plane was overloaded with passengers and equipment, and the pilot was later found to have alcohol and cocaine in his system. Just after takeoff, the plane crashed, killing all nine people on board. Aaliyah, the coolest person in the world, was dead at 22.
Aaliyah did a lot in those 22 years. She managed to put her past with R. Kelly completely behind her, reinventing herself and reworking the sound of commercial R&B in the process. She could’ve done so much more. At the time of her death, Aaliyah was in a happy grown-up relationship with Roc-A-Fella Records co-founder Dame Dash. She’d also started to film her scenes in The Matrix Reloaded. (Nona Gaye replaced her in the movie.) Given everything she’d already done, it’s possible to imagine Aaliyah going on to become some combination of Beyoncé and Sade. We’ll never know.
Aaliyah’s death fucked me up. It fucked a lot of people up. Missy, Timbaland, and Aaliyah’s other peers paid her constant tribute for years. The self-titled album went double platinum, and “Rock The Boat” peaked at #14. Aaliyah would go on to land one posthumous top-10 hit after the release of her 2002 compilation I Care 4 U. “Miss You,” a song that didn’t make the cut for the self-titled album, peaked at #3. (It’s a 7.) I’ve always found DMX’s intro to the “Miss You” video tremendously moving.
There’s been all kinds of intra-family drama over Aaliyah’s music after her death. Drake, a guy with a prominent Aaliyah tattoo, was supposedly going to produce a posthumous album at one point; it never happened. For a long time, Aaliyah’s music wasn’t on streaming services; her records finally showed up with a whole lot of ballyhoo last year. This past December saw the release of “Poison,” a posthumous collaboration with the Weeknd. The track used Aaliyah vocals that clearly weren’t intended for release, and it pissed a lot of fans off. The song didn’t chart. (Drake and the Weeknd will both appear in this column many times.) Apparently, there’s a full posthumous album ready to go, but nobody has any idea if or when it will come out.
But all the chaos surrounding Aaliyah’s estate hasn’t marred her legacy one bit. When she was alive, Aaliyah operated on a whole different level. She seemed to see colors that nobody else could, and her music anticipated a fully digital pop landscape in ways that her peers couldn’t have imagined. She was the future. Even now that she’s more than 20 years gone, she might still be the coolest person in the world.
BONUS BEATS: Here’s dancehall great Bounty Killer interpolating the “Try Again” melody on his 2001 track “Proceed”:
(Bounty Killer’s highest-charting single as lead artist is the 1998 Mobb Deep/Big Noyd collab “Deadly Zone,” which peaked at #78. As a guest, Bounty Killer appeared on No Doubt’s 2001 hit “Hey Baby,” which peaked at #5. It’s a 7.)
BONUS BONUS BEATS: George Michael, a man who’s appeared in this column a bunch of times, sampled the wormy “Try Again” synth-bass on his 2002 single “Freeek!” Here’s the video:
BONUS BONUS BONUS BEATS: Here’s James Blake sampling “Try Again” to disorienting effect on his 2010 track “I’ll Stay”:
(James Blake doesn’t have any Hot 100 hits as lead artist, but he got to #21 when he participated in the Kendrick Lamar/Jay Rock/Future collab “King’s Dead.”)
BONUS BONUS BONUS BONUS BEATS: Here’s YG flipping Timbaland’s “been a long time” line, which itself was a Rakim flip, on 2016’s “Been A Long Time,” a DJ Mustard track that also features Ty Dolla $ign:
(DJ Mustard’s highest-charting single, the 2019 Roddy Ricch collab “Ballin’,” peaked at #11. YG’s highest-charting single as lead artist is the 2018 2 Chainz/Big Sean/Nicki Minaj collab “Big Bank,” which peaked at #16. YG also guested on Jeremih’s 2014 track “Don’t Tell ‘Em,” a Mustard production that peaked at #6. It’s a 10. As lead artist, Ty Dolla $ign’s highest-charting single is the 2014 B.o.B. collab “Paranoid,” which peaked at #29. As a guest, Ty Dolla $ign will eventually appear in this column.)
The Number Ones: Twenty Chart-Topping Hits That Reveal The History Of Pop Music is out 11/15 via Hachette Books. You can pre-order it here.