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. Book Bonus Beat: The Number Ones: Twenty Chart-Topping Hits That Reveal the History of Pop Music.
2014 was a silly time. That entire summer, the hottest star in all of pop music was Iggy Azalea, a white Australian woman who rapped in a Black American accent. For a few months, this lady cranked out hit after hit, and people got into sincere debates over whether she was a flagrant appropriator or just a living indicator that rap had gone global. After a few months, the world took a deep breath, stepped back, and decided that the Iggy Azalea experiment was over. It was an interesting time to be alive.
During her brief and flummoxing reign, Iggy Azalea popped up on three big, buoyant top-10 hits — always over a bouncy and clubby beat, always next to a different female pop singer. Iggy had been working hard to appeal to rap’s core fanbase, and she’d cultivated relationships with some of the genre’s biggest names. But the only person who seemed to believe that Iggy had any rap credibility was Iggy herself. Her try-hard intensity was a fun little gimmick, a novelty, until it became so actively embarrassing that all those rap figures stepped away from her. More than two decades after Vanilla Ice topped the Hot 100, we had another goofy white rapper who followed basically the same trajectory.
“Fancy,” the biggest of those Iggy Azalea hits, uses her strange determination as a comedic bit. It works OK, especially when paired with a sticky beat and an extremely catchy chorus. The song’s (great) video made Iggy out to be a sort of screwball bombshell. If you were feeling charitable, you could choose to look at the entire Iggy Azalea experiment as a piece of self-aware comedy, at least until Iggy herself erased any chance of that.
The Iggy Azalea persona worked until it didn’t. When it worked, Iggy Azalea’s success seemed like a sign that corporate forces were trying to turn rap into something disposable and unrecognizable, and maybe they were. But the moment passed, and now the whole thing just looks absolutely ridiculous. Iggy Azalea doesn’t come off great in this story, but neither does the country that sent “Fancy” to #1. We just keep doing shit like this. We’ve done it a bunch of times, and we’ll probably do it again. We could be doing it right now. Jack Harlow has probably been around too long and earned too much respect to meet that fate. A decade from now, though, maybe we’ll look at Harlow the way we look at Iggy now. I hope not, for Jack Harlow’s sake. I wouldn’t want that for anyone.
From a certain perspective — one that pointedly and probably purposefully ignores the way race works in America — you could frame Iggy Azalea’s big chart moment as an underdog triumph, a testament to the power of the human spirit. Iggy Azalea wasn’t a nepo baby. She didn’t come from a rich family, and she had to make her own connections. Again and again, Iggy bet on herself, trusting her own talent and magnetism to reach places that no white Australian woman had ever been. She caught a lot of lucky breaks, but she wouldn’t have gotten anywhere without a deranged sense of confidence. If all of us believed in ourselves as much as Iggy Azalea did, the world would be even more chaotic than it is today.
Amethyst Amelia Kelly — what a name! — was born in Sydney, but she mostly grew up in a New South Wales town called Mullumbimby. (I’m not making the word “Mullumbimby” up. That’s what it’s called. When Iggy Ig was born, Madonna’s “Vogue” was the #1 song in both America and Australia.) Iggy’s parents were both working-class hippies. Her father was an artist, and her mother worked in housekeeping. As a kid, Iggy fell in love with rap music and tried to teach herself to rap. Along with a couple of friends, she started a kiddie rap group, but she got fed up when the other two wouldn’t take it seriously. Why would they? Why would three kids in New South Wales possibly think that they could make it as rappers?
But that’s how Iggy Azalea felt. She was going to move to America and become a rapper, and nobody could stop her. She dropped out of high school and went to work with her mother, cleaning hotel rooms and saving money. In a great Jezebel story called “The Making And Unmaking Of Iggy Azalea” — one that you now have to read on message boards because Jezebel’s former owners are dumber than dirt — Clover Hope found all sorts of illuminating quotes from Iggy, like this one: “I just knew I wanted to go to America and be a rapper and have a ponytail and a leopardskin jacket that went down to my feet, and, like, 20 white, fluffy dogs on one leash.” It’s the sort of thing that you say when you understand the glamor of rap and not the context behind it. I get it. I’m a clueless white person who loves rap, too. But when you’re a clueless white person who loves rap, it’s incumbent on you to become slightly less clueless.
Before she turned 16, Iggy Azalea bought a one-way ticket to Miami, telling her parents that she was just going on vacation. My parents would’ve lost their shit if 15-year-old me attempted to go on vacation in a foreign land, but maybe Australian hippie parents are different. In Miami, Iggy lived as an illegal immigrant, crashing with a boyfriend and working under-the-table jobs. After a few months, she headed off to Houston, where she met Mr. Lee, a veteran rap producer who’d heard her music on MySpace. He recorded some demos with her and tried to mold her into a more natural rapper. That second part was hard going. Rap did not come naturally to Iggy Azalea.
When she worked with Mr. Lee, Iggy Azalea wasn’t Iggy Azalea yet. She went by the name Regal, but she already rapped in a strange and stilted blaccent. When asked about that voice, she said that she picked a lot of things up by living in the South, but she still talked like an Australian person. The rap voice was all affectation. Mr. Lee introduced Iggy to her first serious boyfriend, a former Christian rapper who was significantly older and who signed Iggy to a management contract that was later ruled invalid. Together, they moved to Atlanta and then broke up messily.
In Atlanta, Iggy Azalea met Backbone, one of the lesser-known members of the Dungeon Family, arguably the greatest rap crew that has ever existed. Backbone helped school Iggy in how to rap, and he continued to say nice things about her years later. Soon afterward, Iggy came into contact with Polow Da Don, a producer whose work has been in this column a few times. For a while, Iggy lived in Polow’s LA house as he tried to develop her as an artist. But Polow wanted Iggy to become a pop star, and she saw herself as a hardcore street-rapper. They went their separate ways.
In the early ’10s, people in the music industry were already looking at Iggy Azalea as a potential star. She was pretty and charismatic, and she obviously loved rap music, but there was such strange dissonance in her persona. People figured — correctly, it turned out — that there was money to be made. During that stretch, Iggy stopped calling herself Regal and adapted the Iggy Azalea stage name. It’s her porn star name. You remember the porn star name thing? Your first name is your childhood pet, and your last name is the street where you grew up? That’s how she got to “Iggy Azalea.” (My porn-star name is Winston Rossiter. I think that’s pretty good.)
In 2011, Iggy Azalea released a mixtape called Ignorant Art. The tape had guest appearances from credible West Coast rappers like YG and Problem, and it also had a minor viral hit called “Pu$$y.” In the video, Iggy struck poses in Black LA neighborhoods, looking like she’d teleported in from another planet. That was the whole appeal: She didn’t belong, but there she was. Soon afterward, she started working with T.I., someone who’s already been in this column a bunch of times. For a minute, Iggy was supposed to be part of T.I.’s Grand Hustle label, but she’d already signed a bunch of contracts, and her label situation was too complicated for that to work out. Still, she made a bunch of tracks with T.I., and he served as executive producer of her 2012 EP Glory. T.I.’s cosign was hugely important to Iggy’s career; it helped people see her as something other than a cartoon character.
In 2012, Iggy Azalea appeared on the same XXL Freshman 10 cover as Macklemore, someone who’s already been in this column a couple of times. Right around then, she was dating fellow up-and-coming rapper A$AP Rocky. I vividly remember her promising that she was making an album optimistically titled The New Classic and posting a photo with two album titles tattooed on her fingers: her own record and Rocky’s LIVE.LOVE.A$AP. After they broke up, she had the A$AP part of the tattoo crossed out. (Rocky’s highest-charting lead-artist single, the 2012 Drake/Kendrick Lamar/2 Chainz collab “Fuckin’ Problems,” peaked at #8. It’s a 9, both as a song and as a time capsule. As a guest on G-Eazy’s “No Limit,” Rocky also made it as high as #4 in 2017. That one is an 8.)
Iggy Azalea’s ascent wasn’t terribly smooth. Her album was pushed back for literal years before it finally came out. She happened to come up around the same time as Azealia Banks, who took exception to her name and general existence. Banks got into online wars with a whole lot of people, but it still became news when she told Iggy to kill herself. And then there was the whole flap around “D.R.U.G.S.,” the mixtape track where Iggy literally rapped the line “I’m a runaway slave master” — quite possibly the worst thing that a white rapper could say. The Clover Hope Jezebel piece infers that the line came from a Black ghostwriter, who just didn’t think before giving it to her.
Whenever anyone would confront Iggy Azalea about general ignorance, she’d scoff and dismiss it. She was working hard, she had other artists behind her, and she wasn’t going to let it bother her. Iggy knew that her success was unlikely, especially in a male-dominated genre like rap, and she took her come-up as a sign that she was doing things right. There wasn’t a whole lot of self-examination happening. This made her very funny. My favorite Iggy Azalea internet moment is the one where she went viral for rapping literal gibberish. She was trying to perform “D.R.U.G.S.,” the “runaway slave master” song, but you couldn’t tell. That shit was gold.
While she was becoming more and more online-famous, Iggy shuffled from label to label before ending up on Def Jam. She recorded most of her album — she really did call it The New Classic — with a production trio called the Invisible Men. Two of the three Invisible Men, Jason Pebworth and George Astasio, had been members of Orson, a band that started out in California but had most of their success in the UK. (Orson’s 2006 single “No Tomorrow” was a UK #1.) The third Invisible Man was Jon Shave, who’d been a member of Xenomania, the production crew behind some very fun British dance-pop hits from groups like Sugababes and Girls Aloud. The Invisible Men started out making tracks for UK stars like Girls Aloud and Jessie J. I’m not quite clear on how they became Iggy Azalea’s main collaborators, but that’s what happened.
Iggy Azalea’s Invisible Men-produced 2013 single “Work” didn’t reach the Hot 100 until she was already famous; it eventually peaked at #54. Follow-up “Bounce” didn’t go anywhere. But then came “Fancy,” the song that became Iggy Azalea’s breakout. “Fancy” took a while to reach its final form. An early, unfinished version of “Fancy,” then known as “Leave It,” leaked in 2013. The Invisible Men co-produced the beat with Kurtis McKenzie, another British producer who was known as the Arcade at the time. When the track leaked, though, people thought it was a DJ Mustard beat. You could understand their confusion.
DJ Mustard, a giant of LA rap, emerged in the early ’10s with a distinctive, immediately recognizable style. Mustard beats were fast, propulsive, and minimal. They used snaps, chants, one-finger keyboard riffs, and a whole lot of negative space. I loved that sound. Mustard essentially defined the sound of fast-rising California artists like YG and Ty Dolla $ign, and he made big hits with people like Tyga and Jeremih. (Mustard only just produced his first Hot 100 chart-topper; that’s going to be a fun column.) The “Leave It” beat was a straight-up ripoff of the DJ Mustard sound. When it took off, Mustard was pissed off, and he was right to be. It’s a pretty good Mustard bite, though. That bouncy, minimal bassline goes hard.
“Leave It” didn’t get a proper release after it leaked. Instead, the Invisible Men figured out that the song would sound better with another artist on it. Without consulting Iggy Azalea, they brought it to Charli XCX, an even younger singer who was starting to have a moment of her own. This was the right decision, and now we get to talk about Charli XCX.
Charlotte Emma Aitchison, the British daughter of a Scottish father and an Indian mother, was born in Cambridge and grew up in Essex. (When Charli was born, Boyz II Men’s “End Of The Road” was the #1 song in America. In the UK, it was Jimmy Nail’s “Ain’t No Doubt,” a song I’d never heard of until this moment.) As a kid, Charli loved pop music, and she started recording songs and posting them online when she was 14. Within a few years, her parents started driving her to the raves and warehouse parties where she’d been booked to perform. She chose Charli XCX as her stage name because it was her handle on MSN Messenger.
At 18, Charli moved to London, dropped out of art school, and signed with Asylum. Her 2013 debut album True Romance was a great piece of vibed-out, indie-adjacent pop music, and it got a lot of attention on websites like this one, but it didn’t cross over to the mainstream. Instead, Charli’s big breakout moment was a song that she gave away. At a songwriting session with the Swedish producers Patrik Berger and Style Of Eye, Charli co-wrote a dizzy, bratty electro anthem called “I Love It,” but she didn’t think that it fit with her style. Berger gave the song to Swedish duo Icona Pop, and it became an international smash for them. (Over here, “I Love It” peaked at #7. It’s a 10.) Charli is credited as a featured guest on “I Love It,” but only because the Icona Pop members sang over the still-audible vocals from her demo.
Maybe “I Love It” was the reason that the Invisible Men brought their unfinished Iggy Azalea track to Charli XCX. This was a good decision on their part. Charli liked the idea of making a girl-power anthem, and there’s a deliriously bratty energy to the hook she wrote for the song that would become “Fancy.” Iggy’s rapping on the track is brittle and studied, but Charli, singing in a sneery and exaggerated British accent, practically spills over with unforced personality. She almost shouts the chorus, giving the song a riotous sense of glee that it never would’ve otherwise had. Her bridge on the track is fucking great: “Trash the hotel! Let’s get drunk on the minibar!” That part alone probably raises the song’s score by one point.
In its final form, “Fancy” is a ridiculous song, but it seems to be ridiculous on purpose. When Iggy Azalea starts the song off by saying, “First things first, I’m the realest,” is she joking? Is she inviting us to consider what it means to be the realest? Or does she just have no idea? She probably has no idea. That’s fine! Some songs arrive at irony through authorial intent, and some just get there by accident. On “Fancy,” Iggy says, “I’m still in the Murda Bizness/ I can hold you down like I’m giving lessons in physics” — a convoluted-ass punchline that doesn’t even land. She borrows a Nas line about bringing ’88 back. She uses an unfortunate R-slur to describe her flow. She almost certainly has no idea what she’s saying, but the song’s bounce is infectious enough that you could have fun with it anyway.
That’s the thing with Iggy Azalea: Even on her best songs, she’s always the worst element. Her rapping is just genuinely unpleasant. You can hear her trying to bluff her way into this image of herself that she’s visualized, the one with the leopard jacket and the 20 fluffy dogs, but that person doesn’t exist. Instead, we hear Iggy doing a dress-up approximation, effortfully broadcasting some misguided idea of glamor. It’s clumsy and awkward and halfassed, and it doesn’t work.
But Iggy does have energy, and when the song is constructed just right around that energy, she does her best to get out of its way. On “Fancy,” she’s got this stupid-fun street-urchin Charli XCX chorus and this catchy fake DJ Mustard beat, and the blips and bloops and singsong hooks do all the things that Iggy herself can’t do. The catchiest Iggy Azalea part of “Fancy” isn’t anything that Iggy herself does; it’s the bit at the end where the producers sample two unrelated bits from Iggy’s verses — “who dat, who dat,” “I-G-G-Y” — and mix them together.
You can never tell with these things, but I’m pretty sure the main reason that “Fancy” caught fire was the video. Director X, one of history’s greatest rap-video auteurs, had the bright idea to turn the clip into a Clueless homage, with Iggy Azalea dressed up just like Alicia Silverstone’s Cher Horowitz character. The imagery fit the song beautifully, and it minimized the weird racial undertones that came with every other Iggy clip. Instead of trying to play catchup to other rappers, Iggy got to act like a cartoon character in a world that was bright and sunny to the point of being fantastical.
The “Fancy” video delights in his own frivolity, and the Clueless flashback arrived right on time for the 20-year nostalgia cycle. The video became a phenomenon, and it’s got more than a billion views now. Alicia Silverstone herself got in on the action a couple of years later, breaking out the Cher costume to do “Fancy” on Lip-Sync Battle. Clueless, by the way, is a really good movie. I kind of wish I was watching it right now, not writing about “Fancy.”
“Fancy” raced up the charts and kicked off the summer of Iggy Azalea. The week that it reached #1, Iggy happened to have a verse on the #2 song in America, so she sort of had the top two spots at the same time. (More on that below.) Later that summer, Iggy made it to #3 with “Black Widow,” a track that Katy Perry co-wrote and Stargate produced. Before blowing up, Iggy opened for the British singer Rita Ora on tour, and Ora sang the hook on “Black Widow.” Once again, Iggy Azalea was the worst part of an otherwise-impeccable pop song. (It’s a 6. Rita Ora’s highest-charting lead-artist single, 2012’s “How We Do (Party),” peaked at #62.)
For a minute, Iggy Azalea was a major star, and lots of people weren’t sure how to feel about that. The “Fancy” single eventually went platinum nine times over. The New Classic, not a big seller at first, went platinum in 2016. But the Iggy bubble popped quickly, and she hasn’t been back in the top 10 since “Black Widow.” Later in 2014, she released “Beg For It,” a song that fit her formula perfectly — Invisible Men production, Charli XCX co-writer credit, hook from Swedish singer MØ — but it only made it to #27.
For a while, Iggy Azalea did guest verses on singles from pop stars looking for comebacks. She teamed up with Britney Spears on “Pretty Girls,” a song about being pretty girls, and with Jennifer Lopez on “Booty,” a song about having nice butts. Both of those sweaty hit attempts fell short, with “Pretty Girls” topping out at #29 and “Booty” stalling at #18. In the meantime, Iggy continued to display a profound lack of self-awareness. At one point, someone posted a photo of Iggy and Macklemore, captioning it “the king and queen of rap.” That one went viral for all the unfortunate reasons that you’d imagine.
Iggy Azalea’s hits dried up quickly. A planned tour was cancelled. A second album never got off the ground. In 2015, Iggy got engaged to Lakers player Nick Young, but the engagement ended when one of Young’s teammates leaked a locker-room video where he bragged about cheating on her. In 2016, Iggy went back to Australia and served as a judge on her homeland’s version of The X Factor for a season. After a bunch of label issues, Iggy finally parted ways with Def Jam and released her sophomore album independently in 2019. It was called In My Defense, and you can tell things aren’t going well when that’s the title of your second album. Lead single “Sally Walker” peaked at #62, and Iggy hasn’t been back on the Hot 100 since.
In 2019 or 2020, Iggy Azalea became a mom, having a baby with Playboi Carti, an Atlanta rapper whose whole vibe does not exactly scream “attentive boyfriend and father.” The relationship didn’t last, and she claimed that Carti refused to spend time with the kid or to sign his birth certificate. (Carti’s highest-charting lead-artist single, 2017’s “Magnolia,” peaked at #29. As a guest, Carti will eventually appear in this column.) Earlier this year, Iggy tweeted some stuff about how she’s retiring from music. Rapper retirements don’t generally stick, and I could imagine Iggy making some kind of comeback down the road, but I can’t see her becoming a star again. She was a brief aberration, and now she’s a cautionary tale. It happens.
Just like Iggy Azalea, Charli XCX scored another big hit in the immediate aftermath of “Fancy.” A week after “Fancy” reached #1, Charli released “Boom Clap,” a dizzy love song that she made for the soundtrack of the movie The Fault In Our Stars. It became the biggest hit of Charli’s career, at least among the tracks where she’s the lead artist, and it reached #8. (It’s an 8.)
Charli released her sophomore album Sucker in 2014. It’s a clear bid for mainstream pop stardom that goes for the anarchic glee of “I Love It” and mostly gets there. I really like that album, but it bricked pretty hard. Lead single “Break The Rules” peaked at #91, and then Charli didn’t make another Hot 100 appearance for almost a decade. (She finally got back on the big chart last year, when “Speed Drive,” her song for the Barbie soundtrack, peaked at #73.)
From there, Charli could’ve readjusted her style, chasing whatever was left of the fractured mainstream pop zeitgeist. Instead, she zagged into experimental maximalism, working with deconstructionist producers like A. G. Cook and the late SOPHIE, making wild and jagged club bugouts like “Vroom Vroom” and misty synth meditations like “White Mercedes.” Those songs were destined for cult-favorite status, and they were never, ever going to crack the pop charts. Instead, as Robyn went inactive for years at a time, Charli assumed her leftfield weird-pop throne. For the most part, Charli has stayed in that zone ever since, and she’s built a truly great career.
Every once in a while, Charli flirts with the mainstream. She opened Taylor Swift’s Reputation stadium tour in 2018, and she tried for something a little more straightforward on Crash, a really great 2022 album that she’s already kinda-sorta disowned. “Good Ones,” that LP’s lead single, is something that I need to hear at least once a week. That song is just amazing. Charli has also maintained a presumably-lucrative sideline co-writing tracks for her more-famous pop peers. In 2015, for instance, Charli was partly responsible for “Same Old Love,” a #5 hit for Selena Gomez. (It’s a 7. Gomez will eventually appear in this column.) In that capacity, Charli XCX will actually appear in this column again.
In recent years, the pop charts have become a little more open to the weirder, more jagged seams-shown sounds that Charli XCX has helped to popularize. It’s possible that Charli will get another big pop-chart moment, but she doesn’t need one. Charli’s new album Brat comes out next week, and I can’t wait to hear it. Later this year, she’s touring American arenas with Troye Sivan and Shygirl, and I would very much like to go to one of those shows. Charli is doing great. Some weirdos, like Iggy Azalea, were never meant for long-term careers in the public eye. Other weirdos, like Charli XCX, were built to last.
GRADE: 5/10
BONUS BEATS: “Weird Al” Yankovic parodied “Fancy” with “Handy,” a fixing-stuff song from his 2014 album Mandatory Fun. Since that’s the most recent Weird Al album, I think that this might be the last time I get to drop one of his parodies into the Bonus Beats section. I could definitely be forgetting something, but that’s too bad! Here’s the “Handy” video:
(One more time, with feeling: “Weird Al” Yankovic’s highest-charting single, 2006’s “White & Nerdy,” peaked at #9. It’s a 7.)
BONUS BONUS BEATS: Here’s Killers frontman Brandon Flowers playing the “Fancy” hook while drummer Ronnie Vannucci Jr. does a funny little dance at the 2014 V Festival in London:
(The Killers’ highest-charting single, “Mr. Brightside,” peaked at #10 in 2005. It’s a 10.)
BONUS BONUS BONUS BEATS: Here’s Gary Oldman having fun reciting the “Fancy” lyrics on British radio in 2014:
BONUS BONUS BONUS BONUS BEATS: The producers of Jidenna’s extremely fun 2015 single “Classic Man” ripped off the “Fancy” beat even more blatantly than the producers of “Fancy” ripped off DJ Mustard, and all the writers of “Fancy” got credits on “Classic Man.” “Classic Man,” for the record, is a much better song than “Fancy.” Somewhere on the internet, there’s video of me drunkenly singing along with “Classic Man” at a 2015 backyard party, and I sincerely hope that you do not find it. Here’s the “Classic Man” video:
(“Classic Man” peaked at #22.)
THE NUMBER TWOS: Remember how I said Iggy Azalea was on the top two songs at the same time? She dropped an energetic verse at the end of “Problem,” a horn-squawking sugar-bomb from Ariana Grande, someone who will be in this column a bunch of times. Honestly, I’m not even mad at Iggy’s verse; the song is just too much fun. “Problem” peaked at #2 behind “Fancy.” It’s a 9.
The Number Ones: Twenty Chart-Topping Hits That Reveal The History Of Pop Music is out now on paperback via Hachette Books. You should want a bad book like this. Buy it here.
