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.
Before I get into today’s column, please allow me a quick moment for self-promotion. In this column, I’ve mentioned a few times that I’ve written a book. I now have the green-light to properly announce some things about The Number Ones: Twenty Chart-Topping Hits That Reveal The History Of Pop Music. This is a completely original book, with nothing reprinted from the column, but it’s definitely intended as a sort of period piece. I picked 20 songs that serve as fulcrum points in chart history — songs that either changed things or signaled that things had already changed. Here’s the promotional copy:
Beloved music critic Tom Breihan’s fascinating narrative of the story of popular music through the lens of twenty game-changing number one singles from throughout the history of the Billboard Hot 100, inspired by the author’s ongoing Stereogum column.
When Tom Breihan launched his column in early 2018, “The Number Ones” — a space in which he has been writing about every #1 hit in the history of the Billboard Hot 100, in chronological order — he figured he’d post capsule-size reviews for each song. But as he dug in, he realized there was so much more to uncover. The column expanded to full-on essays, in which Breihan unpacks the history of each track, its place in the culture at the time, its legacy (or lack thereof), and, of course, the song itself. The column has taken on a life of its own, sparking online debate, attracting constant readers, and occasionally death threats from, say, the guy who wrote “Tie A Yellow Ribbon Round the Ole Oak Tree.”
The Billboard Hot 100 began in 1958, and after four years of the column, Breihan is still in the mid-‘90s, with decades of music and years of posting to come. But readers will no longer have to wait for Breihan’s brilliant synthesis of what the history of number ones has meant to music and our culture. In The Number Ones, he writes about twenty game-changing #1s throughout chart history, revealing remarkably fluid and connected story of music that is as entertaining as it is enlightening. He marks the greatest pop artists of all time, from the Brill Building songwriters to the Beatles and the Beach Boys; from Motown to Michael Jackson, Prince, and Mariah Carey; and from the social media revolution and the Korean pop system. Breihan also ponders great artists who have never hit the top spot, like Bob Dylan, Bruce Springsteen, and James Brown. Breihan illuminates what makes the indelible ear candy across the decades, leaving readers to wonder what could possibly happen next.
I didn’t write that copy, by the way. I would never refer to myself as a “beloved music critic,” though I definitely appreciate the sentiment. You can pre-order the book here.
OK. I’m done with the self-promotional stuff. Here’s the column itself.
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At this particular point in the grand arc of history, the story of Will Smith looks something like a Greek tragedy. Picture it: Teenage rap phenom emerges and displays wild amounts of charisma. Within five years, he’s a sitcom leading man. Within 10, he’s the biggest movie star in the world. He keeps making rap music, almost for fun, and his doofy little side-hustle songs become global hits. The man’s movie career goes through peaks and dips, and he learns to adjust his persona for a changing world, mugging on talk shows and Instagram and TikTok. For him, celebrity is a problem to be solved, and charm is a science to be perfected.
The whole time, this man longs for acceptance from the Hollywood community — a nebulous yearning that takes tangible physical shape in the form of an Oscar. Will Smith gets nominated a few times, but he never quite feels like he belongs. After decades, he finally gets there, swinging into another Oscar race as the frontrunner for Best Actor. Mere minutes before he finally gets that Oscar, Smith goes through what I guess you’d have to call a violent emotional breakdown. He smacks a comedian in the face in front of the world, then goes back to sit in his seat and continues yelling at the comedian. In his rap career, Smith had studiously avoided cussing, to the point where his clean language was almost a gimmick. In his biggest and weirdest moment, the TV censors have to make the whole thing silent because he’s screaming about how Chris Rock should keep Smith’s wife’s name out of Rock’s fucking mouth.
For decades, Will Smith carefully and painstakingly crafted and maintained his public image. When he was on the precipice of some final triumph, the man just lost it. The conversation surrounding the slap was overheated and ridiculous, and it immediately revealed which commentators have ever been smacked in the face and which have not. For those who have never been smacked in the face: I am happy for you. You have grown up in loving homes and breezed your way past potentially violent pitfalls, and that’s great. But perhaps you have lost sight of the fact that people get smacked in the face every day, and that it’s not necessarily that big a deal. (Sometimes, it is a big deal, especially when it’s part of a larger pattern. Sometimes, it’s just some shit that happens.) If you’re wondering why a SWAT team didn’t charge into the Dolby Theatre to handcuff Will Smith, I would beg you to consider the possibility that you don’t know shit about shit.
The past few months in Will Smith discourse have been rough, and it’s hard to even imagine what will become of Smith’s career when he returns to the public eye. (He will return to the public eye, right?) In the context of “Gettin’ Jiggy Wit It,” Will Smith’s first #1 hit, the whole situation becomes even more strange. At one point in history, Will Smith seemed like he had everything figured out. He was the king of popular culture, and a chart-topping hit was light work — a thing to do in between blockbuster films. The man glided effortlessly through the world. His new joint hit, and the world just couldn’t sit. We had to get jiggy wit it.
Will Smith was my first favorite rapper. He was probably a lot of people’s first favorite rapper — especially people like me, relatively comfortable white folks who were kids in the ’80s. In the late-’80s moment when rap music was first becoming a widespread cultural phenomenon, Will Smith made himself a gateway drug. He told silly stories, and you didn’t need to decipher any slanguistics to understand what he was saying. His videos were bright and vivid, and his persona was fun-loving and deeply unthreatening. He presented rap music as something with no barrier to entry — wholesome family entertainment, almost.
If you were paying attention to the music, Smith’s sitcom stardom wasn’t a surprise. If you were paying attention to his sitcom, Smith’s movie stardom wasn’t a surprise. The man had the kind of generational charisma that could easily be transferred from one art form to another. Rap was merely his first vehicle. He made it look easy, the way he made everything look easy.
In West Philadelphia, Willard Carroll Smith II was born and raised. (When Will Smith was born, the #1 song in America was Jeannie C. Riley’s “Harper Valley PTA,” so maybe it’s appropriate that gossip followed this man for his whole adult life.) Smith’s family wasn’t rich, but it was upright and stable. His parents stayed together. His father had served in the Air Force, and his mother had graduated from Carnegie Mellon. When Smith started writing raps as a little kid, his grandmother discovered his notebook and left a note on it, admonishing him to express himself without using filthy language. Smith never cussed in his music again.
One night in 1985, a teenage Will Smith went to a house party on his block. The evening’s entertainment was DJ Jazzy Jeff, a local turntable wizard a few years older than Smith. Jeff was already developing a local reputation, and that night, his hypeman didn’t show up at the party until late. On the spur of the moment, Smith got up onstage and rapped while Jeff scratched records, and the two immediately locked into an easy chemistry. They knew that they had an act.
In 1986, DJ Jazzy Jeff & The Fresh Prince released their debut single “Girls Ain’t Nothing But Trouble” on the local Philadelphia indie Word-Up. While Jeff scratched up the I Dream of Jeannie theme music, Will told self-deprecating stories of romantic misadventures — three different dates that ended in deep frustration. The first verse, in which Will gets hit with a false rape charge, has not aged terribly well. But this was the ’80s, when virtually every high-school comedy had at least 1 million rape jokes. In the context of its day, “Girls Ain’t Nothing But Trouble” was light and fluffy and approachable. Smith wasn’t Run-DMC; he was the guy who misses the Run-DMC show because his date takes too long getting ready. In the cartoonish video, Smith already looks like a sitcom star.
“Girls Ain’t Nothing But Trouble” arrived at a time when very few big rap records came from anywhere other than New York. The song still caught fire, ultimately reaching #57 on the Hot 100 during a period where rap barely ever charted. That single and the 1987 album Rock The House got DJ Jazzy Jeff & The Fresh Prince a deal with Jive Records. They went out on the road with Public Enemy and 2 Live Crew, which must’ve been a truly wild triple bill to witness, and Jive re-released Rock The House; it eventually went gold. At the time, every big rap act had a different sort of character, and these two found their niche. DJ Jazzy Jeff was a ridiculously skilled DJ, which won them respect. The Fresh Prince, meanwhile, was an approachable cornball entertainer, and that got them paid.
The duo broke out huge with the 1988 sophomore album He’s The DJ, I’m The Rapper. The big hit was “Parents Just Don’t Understand,” another sitcom-style story-song about everything going wrong for Will Smith. That song peaked at #12, and it made Jazzy Jeff and the Fresh Prince the winners of the first-ever rap Grammy. This seemed like classic Grammy bullshit: Institutional recognition for the cuddly pop version of the genre rather than its artistic bleeding edge. In solidarity with the other nominees, the duo boycotted the awards show because the rap award wasn’t part of the telecast.
That bit of protest did not hurt their commercial fortunes. He’s The DJ, I’m The Rapper went triple platinum, and another single, “A Nightmare On My Street,” reached #15. That was the one that hooked me. Rapping about getting killed by Freddy Krueger? Incredible. I couldn’t believe it. The Nightmare On Elm Street franchise didn’t approve Jeff and Prince’s song, but it made great use of the sampled score, and it was a whole lot better than the Fat Boys’ “Are You Ready For Freddy,” the rap song that appeared on the actual Nightmare 4 soundtrack.
The duo’s next album, 1989’s And In This Corner… flopped hard, and its single “I Think I Can Beat Mike Tyson,” peaked at #58. This was a disappointment for everyone except, I guess, me. Rapping about getting beat up by Mike Tyson? That was as good as the Freddy Krueger thing! I loved it! Will Smith had been spending money too freely, and he was found guilty of income tax evasion, with the IRS garnishing his income. At an Arsenio Hall taping, the music exec Benny Medina met Smith and pitched him an idea about a sitcom that would tell a fictionalized version of Medina’s own life story. Smith had never acted, and he was skeptical. But Quincy Jones was producing the show, and he convinced Smith to audition for NBC executives during a party at Jones’ house. NBC picked up The Fresh Prince Of Bel-Air, and the show debuted in September 1990.
The Fresh Prince Of Bel-Air was a big hit that stayed on the air for six seasons. Smith played a Philly street kid sent to live with rich relatives in California, and the show kept that fish-out-of-water premise intact throughout. Jazzy Jeff got a recurring role as Jazz, Will’s old neighborhood friend who keeps getting physically thrown out of the mansion by Uncle Phil. While the show was on, Smith kept making music with Jazzy Jeff. In 1991, the duo made the top 10 for the first and only time. On the richly funky “Summertime,” Smith slowed his flow and deepened his voice, doing his best to imitate Rakim. The song peaked at #4. (It’s an 8.)
Will Smith started taking small movie roles in the early ’90s. In 1995, just before Fresh Prince went into its final season, Smith and Martin Lawrence starred in the action-comedy Bad Boys, Michael Bay’s directorial debut. At that point, Smith wasn’t really rapping anymore; he and Jeff had released their last album Code Red in 1993. Bad Boys was a hit. In its wake, Smith and his manager sat down to figure out how to make Smith the biggest movie star in the world. They looked at a list of the highest-grossing films, broke down the elements that ran through them, and turned their script-selection process into something like an algorithm. That’s how Will Smith ended up in Independence Day, the biggest blockbuster of 1996.
After Independence Day, Smith teamed up with Tommy Lee Jones in Barry Sonnenfeld’s Men In Black, which would’ve been the biggest hit of 1997 if Titanic hadn’t come along and made more than twice as much. While working on Men In Black, the production duo known as the Trackmasters pitched an idea to Smith: He should record a song for the soundtrack where he rapped about the plot of the movie. When “Men In Black” came out, I remember being scandalized that Will Smith was using the rap name “Will Smith,” not calling himself the Fresh Prince anymore. My quibbles did not matter. “Men In Black” became a monster hit. It topped the Radio Songs chart for weeks, and it probably would’ve conquered the Hot 100 if it had been released as a single.
At that point, the Trackmasters were the ideal partners for Will Smith. Jean-Claude “Poke” Olivier and Samuel “Tone” Barnes came from Brooklyn, and they started producing rap records in 1989. Their style was bright and slick, with obvious samples mixed in with live instrumentation, and it matched the sound that Puff Daddy was looking for at Uptown Records and then at Bad Boy. The Trackmasters produced big hits for Biggie Smalls, Soul For Real, LL Cool J, and others. They also signed Nas to their Trackmasters Entertainment imprint, and they released his 1994 masterpiece Illmatic but didn’t produce anything on the album. They did however, produce a bunch of stuff on Nas’ slicker follow-up It Was Written, which had something to do with the chillier reception for that album. The Trackmasters made pop-rap, and their style worked best when they teamed up with a rapper who shared their instincts. Nobody had poppier instincts than Will Smith.
After “Men In Black,” Smith teamed up with the Trackmasters to record a whole album. Big Willie Style, Will Smith’s first solo LP, is a profoundly goofy take on the Puff Daddy model. The sounds are bright and flashy, and the samples are obvious. But Will Smith, who’d still been making rap music as the Fresh Prince four years earlier, didn’t really rap like a ’90s rapper. Instead, he had a kind of game-show host vibe — a kind of smooth self-mockery, delivered in the form of sharply enunciated humblebrags. Smith complained about player haters, just like Puffy, but he kept everything rated G. He would talk about women swooning in his presence, but most of his romantic boasts were directed at fellow movie star Jada Pinkett, who became Will Smith’s second wife a few weeks before the release of his single “Gettin’ Jiggy Wit It.”
The Trackmasters produced “Gettin’ Jiggy Wit It” with help from L.E.S., a Queensbridge beatmaker who’d come up with Nas and who’d produced the Illmatic track “Life’s A Bitch.” The “Gettin’ Jiggy Wit It” beat mostly came from the busy bass-popping groove that Chic’s Nile Rodgers and Bernard Edwards had concocted for Sister Sledge’s 1979 disco single “He’s The Greatest Dancer.” (“He’s The Greatest Dancer” peaked at #9. It’s an 8. Sister Sledge’s highest-charting single, 1979’s “We Are Family,” peaked at #2. It’s another 8.) Puff Daddy and his associates had just sampled another Rodgers/Edwards track on Biggie Smalls’ “Mo Money Mo Problems,” so “Gettin’ Jiggy Wit It” became the second single with a Bernard Edwards songwriting credit to reach #1 after Edwards’ 1996 death.
But then, there were a lot of songwriting credits to divide up on “Gettin’ Jiggy Wit It.” The na-na-na bit on the chorus came from “Sang And Dance,” a track that funk greats the Bar-Kays released in 1970. (The Bar-Kays’ highest-charting single, 1967’s “Soul Finger,” peaked at #17.) The Bar-Kays and their collaborator David Porter all got songwriting credits on “Gettin’ Jiggy Wit It.” So did Sugar Hill Records co-founder Joe Robinson, who’d given himself full credit on Spoonie Gee and the Treacherous Three’s great 1980 single “Love Rap.” (I don’t know how that works; “Love Rap” didn’t even come out on Sugar Hill.) Smith quoted the “from south to the west to the east to the north” bit from “Love Rap,” and that was apparently enough for Smith to give away another credit.
The rumor was always that Nas ghost-wrote Will Smith’s “Gettin’ Jiggy Wit It” lyrics. I never put much stock in that, since none of the song’s lyrics sound anything like the sort of thing that Nas would ever say. Nas later clarified that he was in the studio when Smith was working on the song, and he fed Smith a couple of lines, but Will Smith wrote the whole thing himself. I don’t doubt that. The line about the cigar — “Right from Cuba-Cuba, I just bite it/ It’s for the look, I don’t light it” — is irredeemable cheeseball shit. It’s pure Will Smith.
In Fred Bronson’s Billboard Book Of Number 1 Hits, Poke tells the story of how “Gettin’ Jiggy Wit It” came to be. He says the duo played the beat for Smith and he asked what it was called: “I said we should call it ‘Gettin’ Jiggy Wit It,’ and I started doing this cute dance. Everybody was laughing, and we didn’t know what to make of it. But once Will wrote the lyrics, Tone and I thought this might be the one. It was magical.”
The term “jiggy” was some Brooklyn rap shit. It meant fly to the point of flashiness, and it showed up on a bunch of Bad Boy hits. (The Lox have always seemed hugely embarrassed about their Rod Stewart flip “If You Think I’m Jiggy.”) Smith has talked about how he liked how that word flipped the racist slur “jigaboo,” adapting it and using it for empowering ends. Maybe he really was thinking about that, but the word jiggy was already in circulation. Today, when people talk about the period of Bad Boy dominance, those who don’t use the “shiny suit” term call it the jiggy era.
“Gettin’ Jiggy Wit It” is a full on Puff Daddy swagger-jack, even though Will Smith raps nothing like Puff Daddy. He’s a whole lot more energetic than Puffy, but he’s also almost painfully eager to please. The track is more cluttered than what Smith had been making with Jazzy Jeff. (Jeff came in to do the song’s hyperactive record-scratches, which is nice.) If anything, Smith’s rapping on the song calls back to rap’s origins, when rappers were just supposed to fill up space and shout out the DJ. His lyrics are mostly generic party chatter and good-life boasts. I thought it was dumb when Smith bragged about having floor seats to the Lakers instead of the Sixers, and then I though it was even dumber when he rhymed “Philly” with “don’t be silly.” The whole thing annoyed me.
Maybe the problem was that I’d developed an attachment to the Fresh Prince. I knew what he could do, and this was not it. Will Smith knew how to do braggadocious party-rap; he’d made “Brand New Funk.” This was something else. This was a movie star making tinny, joyless watered-down Bad Boy stuff. I couldn’t get into it. Smith’s charm was still palpable, and it went a long way. That Sister Sledge groove was good, too. But the song grated on me. In a weird sort of way, it helped me appreciate what Puff Daddy had been doing. The “Jiggy” video even looked like a cheesier Bad Boy clip. Smith shot it with Hype Williams on the Vegas strip, using the different casino themes to go for Egyptian and Hawaiian kitsch. The little dance and the fisheye lens were fun, though.
I have been rooting for Will Smith for the vast majority of my life, even when he was an oppressively dominant overdog whose cultural footprint was inescapable. I’m rooting for Will Smith now, even after the Oscar slap has made him the subject of way too much online handwringing. But “Gettin’ Jiggy Wit It” has always sounded thoroughly pointless to me. Even with all that charm on display, the song is just swaggerless carnival barking with no clear reason to exist. Smith doesn’t express anything on the song. It feels less like a song and more like a brand extension — a lazy victory lap for a guy who’d won in virtually every way that a guy can win.
In his 2021 memoir, Smith writes that “Gettin’ Jiggy Wit It” was slow to take off but that its fortunes changed after Jerry Seinfeld said something about getting jiggy on a 1998 episode of Seinfeld. A week later, Stuart Scott was yelling about getting jiggy over basketball highlights on SportsCenter. I don’t know about all that. Will Smith was on a wild winning streak, and he says so himself in his book: “So much shit was going absolutely perfectly in my amazing life that, well, I was legitimately embarrassed.” Something tells me that “Jiggy” was doing just fine without Seinfeld’s help.
The success of Big Willie Style was practically assured. The biggest movie star in the world had made his name as a rapper, and then he’d put out a rap record with no cussing at a time when that could be considered a selling point. Big Willie Style sold 9 million copies in the US alone. The next two singles didn’t make the top 10, but they were definitely everywhere. “Just The Two Of Us” had Will Smith flipping the Bill Withers/Grover Washington song of the same name to rap heartfelt messages to his son Trey, the previous-marriage kid who did not grow up to be a famous weirdo. It peaked at #20. After that, “Miami” had Smith using the Whispers’ “And The Beat Goes On” to rap about a city where the heat is on, all night, everyday, to the break of dawn. It peaked at #17.
As the Big Willie Style album cycle died down, Will Smith got back to the lucrative business of movie stardom. In November of 1998, Smith starred alongside Gene Hackman in the Tony Scott thriller Enemy Of The State, the first serious-ish role of his dominant era. Enemy Of The State wasn’t a four-quadrant smash on the level of Independence Day or Men In Black, but it still took in $250 million at the global box office. Smith wasn’t done with music yet, though. We’ll see him in this column again.
GRADE: 4/10
BONUS BEATS: Here’s the strange spectacle of Phish covering “Gettin’ Jiggy Wit It” at a 1998 show:
BONUS BONUS BEATS: Here’s Will Smith himself happily rapping along with “Gettin Jiggy Wit It” at an Oscars afterparty, while holding the Oscar he’d just won, on what might turn out to be the most professionally consequential night of his career:
(Please no jokes about how “Gettin Jiggy Wit It” slaps. It’s been done, and anyway the song does not slap.)
THE 10S: Wyclef Jean’s elegiac, symphonic drug-trafficker lament “Gone Till November” peaked at #7 behind “Gettin Jiggy Wit It.” It makes a hearse out of ya Rolls Royce, and it’s a 10.
