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.
In February of 1989, on the night before his 20th birthday, Bobby Brown headlined Madison Square Garden. New Edition, the group that Brown had left a few years earlier, opened for him. Onstage at the Garden, Brown wore a red boxing robe with “King Of The Stage” stitched across the back. The night ended with Brown singing “My Prerogative,” the defiant anthem that had just spent a week at #1. Singing that song on that stage, Brown was not alone.
During “My Prerogative,” LL Cool J, Heavy D, and Run-DMC’s Run all came out and freestyled verses. Other rap figures like KRS-One and Eric B. stood onstage and watched. Teddy Riley, the young musician who’d just masterminded a whole R&B movement and who’d also essentially ghostwritten and ghost-produced “My Prerogative,” played a keyboard solo. Babyface and LA Reid, two more songwriters and producers who’d had a hand in putting together Brown’s massively successful album Don’t Be Cruel, also stood on that stage. If there’s any footage of that performance, I haven’t been able to find it. But the paper of record was there.
In a breathless New York Times review of Brown’s performance that night, Peter Watrous wrote, “The communal scene on stage mirrored the feeling in the audience; everybody seemed aware that this was a generation that had rewritten the rules of pop entertainment, and was justifiably proud of its achievement.” History would prove Watrous right. By those early months of 1989, rap music had already left a mark on a whole generation’s collective imagination. Rap songs wouldn’t start topping the Hot 100 for a while, but the rumblings were already there. “My Prerogative” isn’t a rap song, and Bobby Brown was not a rapper, though he did like to rap sometimes. But in a lot of ways, “My Prerogative” is really the first #1 rap hit — in spirit, if not, strictly speaking, in sound.
Bobby Brown’s childhood was as wild and violent as that of any rapper. Brown grew up in a Boston housing project, one of eight kids in a working-class family. (When Brown was born, the #1 song in America was Tommy James And The Shondells’ “Crimson And Clover.”) When Brown was three, his mother, a substitute teacher, took him to see James Brown (no relation). During an intermission, she pushed her extremely young son out onstage to dance, and she was impressed at what she saw. But Bobby Brown was not, at first, a stage kid. He was a street kid, and he had the scars to prove it.
As a kid, Bobby Brown would run around in the streets with his friends, stealing stuff. When Brown was 10, he caught a stray bullet in the knee during a block party. When he was 11, he was stabbed in the shoulder, and his friend Jimbo Flint was stabbed to death. (Don’t Be Cruel is dedicated to Flint’s memory.) Brown had things stacked against him, but he also had talent. After those stabbings, Brown got together with a group of local kids and formed a singing group. They called themselves New Edition, and they entered a talent competition sponsored by Maurice Starr, a musician who’d been a part of the electro group Jonzun Crew and who’d just started off what would turn out to be an unsuccessful solo career. (Maurice Starr’s highest-charting single, 1981’s “Dance To The Funky Groove,” peaked at #66.)
New Edition didn’t win that talent contest — a rap group did — but Maurice Starr started working with them anyway. In 1983, New Edition released their ebullient debut single “Candy Girl,” which Starr and his brother Michael Jonzun wrote and produced. The song sounded like post-disco Jackson 5, and it caught on big. “Candy Girl” peaked at #46 on the Hot 100, but it topped the R&B chart, and it also went to #1 in the UK. New Edition signed to MCA and cranked out a bunch of hits; 1984’s “Cool It Now,” their highest-charting single before Brown left, peaked at #4. (It’s a 7.)
New Edition more or less invented the boy-band model as we know it today. The group made breezy, uptempo dance-pop, but their music existed in conversation with the club music of the day; they did a lot of rapping on those early hits. The young singers started New Edition with no svengali. They all played roles within the group dynamic; Ralph Tresvant, for instance, was the focal point, while Bobby Brown was a classic bad-boy type. New Edition figured out those roles themselves.
The kids in New Edition were the ones who created New Edition, but that didn’t stop the older people around them from trying to take advantage of the boys. In 1984, New Edition fired Maurice Starr as their manager; he immediately turned around and assembled a bunch of cute white boys into New Kids On The Block, a soundalike group that will soon appear in this column. Pretty soon afterwards, Bobby Brown quit New Edition.
There have always been conflicting reports as to why Bobby Brown left the group. Some of those stories say that he quit because he was jealous of Tresvant, who went on to a successful solo career of his own. (Tresvant’s highest-charting single, 1990’s “Sensitivity,” peaked at #4. It’s an 8.) Other stories say that Brown got fired because he kept breaking formation, ignoring the choreography to do his own raunchy dance moves. But Brown himself claimed that the money just wasn’t what it was supposed to be. Talking to SPIN‘s Barry Michael Cooper in 1988, Brown said, “The most I saw for all of the tours and all of the records we sold was $500 and a VCR.”
Bobby Brown went solo and signed his own MCA deal, and New Edition replaced him with Johnny Gill, another singer who would go on to solo success after New Edition’s 1990 breakup. (Gill’s highest-charting single, 1990’s “Rub You The Right Way,” peaked at #3. It’s a 9. Meanwhile, the other three members of New Edition went on to form Bell Biv DeVoe, and their two highest-charting singles, 1990’s “Poison” and “Do Me!,” both peaked at #3. “Poison” is a 9, and “Do Me!” is an 8.)
Bobby Brown’s 1986 solo debut King Of Stage was a relative flop, and it didn’t really separate him from his baby-pop-star New Edition persona. Lead single “Girlfriend” went to #1 on the R&B charts, but it peaked at #57 on the Hot 100. So Brown figured out that he needed to change his whole approach. In working on his sophomore LP Don’t Be Cruel, Brown tapped into the sound of new jack swing, the hard, percussive combination of dance, R&B, and rap that was only just becoming a commercial force. New jack swing was new and fierce and just slightly dangerous, and it turned out to be an ideal vehicle for Brown’s hard-strutting confidence.
Working on Don’t Be Cruel, Bobby Brown got together with a group of ascendant R&B producers and songwriters like Babyface, LA Reid, and, most importantly, Teddy Riley. The Harlem native Riley, just two years older than Bobby Brown, had already become the face of new jack swing; Barry Michael Cooper had coined the genre name in a 1987 Village Voice profile of Riley. Riley had formed the trio Guy, whose hard digital funk proved hugely influential, and he’d also produced for rappers like Doug E. Fresh and Kool Moe Dee. (Weirdly, Guy’s highest-charting single is the 1999 reunion song “Dancin’,” which peaked at #19.)
Initially, Riley wasn’t credited for songwriting or production on “My Prerogative” or on anything else from Don’t Be Cruel. Instead, Gene Griffin was credited as producer, and Bobby Brown and Griffin were listed as songwriters. Griffin was the guy who’d invested in Riley’s early production career, and he exploited the hell out of Riley for as long as he could. But Bobby Brown was always open about the fact that Riley and his Guy bandmate Aaron Hall had really written “My Prerogative” and that Riley had produced it. Brown even shouts Riley out multiple times on the song itself: “Yo, Teddy! Kick it like this!” (Aaron Hall’s highest-charting single as a solo artist, 1994’s “I Miss You,” peaked at #14. Teddy Riley will show up in this column again.)
Don’t Be Cruel is almost entirely devoted to new jack swing. Even when Riley wasn’t the one producing, Bobby Brown and his collaborators built on the blueprint that Riley had established: Hard beats, pleading vocals, tons of attitude. That worked beautifully on lead single “Don’t Be Cruel,” which became Brown’s first crossover solo hit, peaking at #8. (It’s a 10.) It worked even better on “My Prerogative.”
“My Prerogative” is an anthem. The song opens with the sound of screeching tires and with a clanging metal-on-metal drum barrage. When the groove locks in, it’s a beast. The drums wallop, and the synthetic bassline sounds like one of the monsters from Tremors burrowing up into a breakdancing circle. All the musical elements on “My Prerogative” — the little melodic synth-hooks bouncing around in the background, the vocoderized backup-singer robots on the outro, the sax-squawks, the Teddy Riley keyboard solo — exist to serve that groove. The “My Prerogative” beat is James Brown’s elemental funk updated for a digital age. It’s loud and harsh and mean, and it moves.
Bobby Brown is completely at home on “My Prerogative.” For Brown, the song was his chance to slap back at anyone gossiping about his exit from New Edition. But “My Prerogative” is about more than that. At a time when news outlets treated young Black men almost exclusively as demonic forces, Brown used the song to give a giant omnidirectional fuck-you. Bobby Brown doesn’t need permission. He makes his own decisions. They say he’s crazy, but he really doesn’t care; that’s his prerogative. They say he’s nasty, but he doesn’t give a damn. Getting girls is how he lives.
“My Prerogative” is really a song about haters, a subject that would become all too common on the charts in the years ahead. Brown doesn’t rap more than a couple of lines on “My Prerogative,” but he carries himself the way a rapper would. He demands to know why they won’t just let him live. He says that he’ll spend his money however he wants. He talks his shit, and he talks it with his whole chest. Even when he’s falsetto-howling, Brown emits total self-possessed arrogance. He sounds like he does not give a fuck about you. It’s inspiring. There’s no retort to “My Prerogative.” Even with the hindsight of decades, with all the wreckage that has come out of Bobby Brown’s personal life, that shit resonates.
The “My Prerogative” video helped, too. The whole clip is built around a club performance, and it’s plainly obvious that the people with the instruments onstage are not playing those instruments on the song. But Brown is all boundless charisma, stepping into and out of the choreography and shamelessly flirting with anyone in his orbit. “My Prerogative” is a physical song, a song built for dancing, and one thing that Bobby Brown can do is dance. The crowd of extras is plainly extremely amped to see him, and he’s just as excited to perform for them. He knows he’s having a moment. (“My Prerogative” video director Alek Keshishian would go on to make Truth Or Dare and With Honors.)
With “My Prerogative,” Bobby Brown fully tapped into the zeitgeist. It’s one of those songs that makes everything else on the charts look timid and boring, and it’s also a crucial bridge between the smoothed-out R&B of the ’80s and the revolutions to come. Brown was a star before “My Prerogative” hit #1, and Don’t Be Cruel was double platinum. But “My Prerogative” attached a rocket to Brown. It’s the hardest song on Don’t Be Cruel, and it’s also the biggest hit. The LP went platinum seven times over, and Billboard named it the biggest-selling album of 1989.
More hits followed. Brown released five singles from Don’t Be Cruel, and all of them went top-10. (“Roni” and “Every Little Step” both peaked at #3. “Roni” is a 7, and “Every Little Step” is a 9. “Rock Wit’cha” peaked at #7. It’s a 6.) While the Don’t Be Cruel album cycle was still happening, Bobby Brown also released “On Our Own,” the single from the Ghostbusters II soundtrack, and that one got as high as #2. (It’s a 9.)
Four months after “My Prerogative” hit #1, Bobby Brown met Whitney Houston at the Soul Train Awards, and they got married three years later. After that, a lot of fucked-up stuff happened, and we’ll get into that soon enough. “My Prerogative” would prove to be Bobby Brown’s only #1 hit as a lead artist. But we’ll see Brown in this column again in a different capacity, and we’ll pick his story up there.
GRADE: 10/10
BONUS BEATS: Here’s Nice & Smooth interpolating the “My Prerogative” hook on their Partridge Family-sampling 1991 classic “Hip Hop Junkies”:
(Nice & Smooth’s highest-charting single, 1991’s “Sometimes I Rhyme Slow,” peaked at #44.)
BONUS BONUS BEATS: Here’s Britney Spears’ video for her not-great 2004 tabloid-bait cover of “My Prerogative”:
(Britney Spears will eventually appear in this column.)
BONUS BONUS BONUS BEATS: Here’s LeBron James singing an experimental atonal rendition of “My Prerogative” while hosting the 2007 ESPYs:
BONUS BONUS BONUS BONUS BEATS: Here’s the baffling moment in the 2007 film Wild Hogs where past Number Ones artist John Travolta sings “My Prerogative”:
BONUS BONUS BONUS BONUS BONUS BEATS: Here’s Natalie Portman singing a bit of “My Prerogative” in her 2018 SNL Digital Short “Natalie’s Rap 2.0”:
(The Lonely Island’s highest-charting single, the 2010 Akon collab “I Just Had Sex,” peaked at #30.)
THE 10S: Michael Jackson’s spartan dancefloor freakout “Smooth Criminal” peaked at #7 behind “My Prerogative.” It leaves the bloodstains on the carpet, and it’s a 10.
