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.

“Havana ooh-na-na.” That’s some good pop songwriting right there. In six syllables, you reduce the name of a major global metropolis to pure gibberish. Little kids who have never even heard the word “Cuba” can sing along to “Havana ooh-na-na,” fully confident that they understand the song completely, and who’s to say that they’re wrong?

On the one hand, “Havana” is an extremely sharp piece of image-creation and positioning. Camila Cabello, a young singer who’d only just left the girl group Fifth Harmony, could use a song like that to establish something resembling a solo identity, tap into the latest pop wave, and ostensibly pay tribute to the city where she was born. If you were tapped into her story, you could see all the pieces working on the track. But “Havana” wasn’t necessarily a song for the people who already knew who Cabello was. It was a song for the world, for the little kids who would sing along with that chorus as if it was nothing but a euphoric syllable-tumble.

“Havana” succeeded wildly on both levels. For a minute there, Camila Cabello looked like a big star in the making. She’s since cooled to mid-sized stardom, but she made a bunch of hits before that happened, and mid-sized stardom isn’t the worst fate anyway. “Havana” also proved to be an improbable little pop breakthrough for Young Thug, a massively important rap figure who’d previously been considered too weird for pop-chart stardom. But “Havana” probably works best on its own terms, as one isolated burst of giddy nonsense. My kids were in elementary school when “Havana” came out, and they used to sing that hook all the time. At least for me, that’s the song’s greatest legacy. If a pop song makes sense on that little-kid level, then everything else becomes secondary.

She really did come from Havana, ooh-na-na. Karla Camila Cabello Estrabao, the daughter of a Mexican father and Cuban mother, was born in Havana’s Cojímar district, and she moved back and forth between Cuba and Mexico when she was a kid. (Perhaps appropriately, the Spice Girls’ “Wannabe” was the #1 song in America when Cabello was born. As far as I can figure, there’s no Cuban singles chart, so I can’t tell you what was at #1 over there.) Cabello and her mother moved to Miami when Cabello was six years old, taking a very long bus ride after Cabello’s mother told her that they were going to Disney World.

At first, it was just Camila Cabello and her mother in Miami; her father wasn’t able to join them for a while. Cabello’s mother had studied architecture in Cuba but she had to find a job at Marshall’s. When her father arrived, he worked at a car wash. Eventually, they started a construction company together. As a teenager, Cabello was socially shy, but she was unfortunately less shy online. Years later, she apologized for reblogging racist jokes on Tumblr. When Cabello was 15, she surprised her family by announcing that she wanted to audition for The X Factor, the American version of Simon Cowell’s hugely successful singing-competition show.

The American X Factor never became a sensation like American Idol or Cowell’s more recent enterprise America’s Got Talent. Our X Factor only lasted three seasons, despite the presence of big-name judges like LA Reid and Britney Spears. Cabello auditioned with Aretha Franklin’s “Respect,” and her audition never aired on the show because they couldn’t clear the song. From there, Cabello’s X Factor run followed an arc that might look familiar. She was eliminated during the show’s boot-camp stage, and then she was brought back when the judges put her into a group with a bunch of other young contestants who’d been cut. That exact same process led to the creation of One Direction on the UK X Factor. In America, we got Fifth Harmony instead.

If you take K-pop out of the equation, Fifth Harmony remain the last classically constructed girl group to find any relevance on the American charts. I don’t say that to disrespect K-pop; groups like Blackpink and NewJeans have made some great music and kept a classic pop format alive. It’s more an illustration of how far the girl group had faded from the limelight before Fifth Harmony came along. In the UK, reality-TV girl groups like Girls Aloud and Little Mix were a big deal, but that didn’t really exist over here. Still, there was something to Fifth Harmony’s covers of poppy pop songs. They had a certain electricity. Just like One Direction before them, Fifth Harmony didn’t win their season, coming in third instead. Just like One Direction before them, Simon Cowell still signed them to his Syco imprint.

Camila Cabello was 16 when Fifth Harmony released their official debut single “Miss Movin’ On” in 2013. It’s a down-the-middle uptempo pop song that peaked at #76. But Fifth Harmony retooled things while working on their first album, 2015’s Reflection. They found a clubby pop sound that leaned heavily on rap and R&B styles and the trope of the sassy, demanding girlboss. They really took off with their briefly inescapable single “Worth It,” which has a guest-verse from pop-rapper Kid Ink and one of the sampled squawking-saxophone riffs that was so popular at the time. That song is catchy as all hell, and it peaked at #13. Reflection went platinum. Fifth Harmony were on their way.

Almost immediately, Camila Cabello established herself as the breakout star of Fifth Harmony, the one who was destined for big things beyond the group. That’s an old pop-music story, and it hits a little harder when the group members aren’t kids who grew up together but aspiring solo stars who all got lumped into one entity for television purposes. In 2015, the same year that Fifth Harmony released Reflection, Cabello teamed up with young heartthrob and future boyfriend Shawn Mendes on his song “I Know What You Did Last Summer.” She became the first Fifth Harmony member to appear on a record without the rest of the group. Her bandmates were apparently not amused. The song peaked at #20. (Shawn Mendes will eventually appear in this column.)

Over the next year, Camila Cabello had more success, both as a member of Fifth Harmony and as a free-floating prospect on the pop landscape. Fifth Harmony once again went platinum with their sophomore album 7/27, and they had their biggest-ever hit with “Work From Home,” a Ty Dolla $ign collab that I absolutely love. (Ty Dolla $ign will eventually appear in this column.) Outside the context of the group, Cabello had another hit by jumping on pop-rapper and future pop-punker Machine Gun Kelly’s “Bad Things,” which I do not love. Her hook is the best part of it, though. (Both “Work From Home” and “Bad Things” peaked at #4. “Work From Home” is a 10, and “Bad Things” is a 5.) Before the year was over, Cabello was out of Fifth Harmony.

The Camila Cabello/Fifth Harmony split was inevitable, and it was messy. The singer and group issued contradictory statements, with Cabello claiming she’d been kicked out and Fifth Harmony claiming that she’d left. The group didn’t last long without her. Their third album was self-titled, even though Fifth Harmony only had four members when it came out in 2017. While performing at that year’s VMAs, the group took a parting shot at Cabello. They appeared on stage as five backlit silhouettes before one of them, Cabello’s apparent avatar, was suddenly jerked away in a bit of Looney Toons slapstick. The stunt got attention, but the album flopped. Its lead single, the Gucci Mane collab “Down,” peaked at #42, and Fifth Harmony never returned to the Hot 100.

Fifth Harmony went on indefinite hiatus in 2018, with all four remaining members attempting solo careers. Of those four, the single-named Normani has been the most successful by far. Her biggest hit, the Sam Smith duet “Dancing With A Stranger,” peaked at #7 in 2019. (It’s a 5. Sam Smith will eventually appear in this column.) Lauren Jauregui doesn’t have any Hot 100 hits of her own, but she did make it to #100 as a guest on Halsey’s 2017 song “Strangers.” Ally Brooke and Dinah Jane have yet to impact the Hot 100 as solo artists.

While Fifth Harmony were in the process of falling apart, Camila Cabello was figuring out how to approach her own solo career. That’s an interesting puzzle, isn’t it? On paper, Cabello was a can’t-miss pop star. She was young and pretty and charismatic, and she could sing. More importantly, she was famous, and the drama surrounding her exit from Fifth Harmony drew more attention to what would’ve already been a big solo-career launch. But Cabello and her team had to figure out how to present the solo Cabello to the world, and a big part of that is figuring out who she was in the first place. That’s not always an easy question to answer.

In 2017, Camila Cabello made guest appearances on tracks from production entities Cashmere Cat and Major Lazer, and she had a song with J Balvin and Pitbull on the Fate Of The Furious soundtrack. But the song that was really supposed to launch Cabello as a solo artist was “Crying In The Club,” a track with an expensive pedigree.

“Crying In The Club” was built on a sample of Christina Aguilera’s “Genie In A Bottle,” and it was largely written by former Number Ones artist Sia. You can see the calculation in all of that, but it didn’t click. “Crying In The Club” is a forgettable song that doesn’t do much to announce Cabello’s pop-star persona. It mostly just sounds like Sia. Later on Cabello’s manager Roger Gold told The New York Times, “The reality of that song is it doesn’t feel or sound like Camila. The most important learning in this whole thing was that we were most successful when Camila trusted in her own instincts.”

“Crying In The Club” underperformed expectations, peaking at #47. When Cabello’s debut album came out, “Crying In The Club” wasn’t even on it. The single came out in May 2017. While it was fizzling on the charts, Cabello released two more songs, both of which were recorded with proven hitmakers but neither of which had huge expectations. One of those songs was “OMG,” which was largely written by former Number Ones artist Charli XCX and which had an appearance from former Number Ones artist Quavo. “OMG” peaked at #81, which seems about right. The other song was “Havana.”

Ten different people, including Camila Cabello and guest-rapper Young Thug, have songwriting credits on “Havana.” It’s a pure product of the song-machine — lots and lots of highly paid professionals putting their heads together to make something that sounds simple and effortless. This isn’t a case where samples add to the number of songwriters, either. There are no samples on “Havana.” Presumably, all these people really added something or other to the final product, and most of us will have a hell of a time figuring out who’s responsible for which parts.

As far as I can tell, “Havana” started off with Adam Feeney, who’s one of those 10 songwriters but who’s also the track’s only credited producer. Back then, Feeney was known professionally as Frank Dukes, after the guy who Van Damme played in Bloodsport. Now, he calls himself Ging. He should’ve stuck with Frank Dukes. I’ll be calling him Dukes in this column. Dukes is from Toronto, and he got his start as one of these musicians who makes sounds for other producers to sample when they don’t want to pay to sample old records. Dukes started making rap beats in the early ’00s, and he worked with Drake back when Drake was a mixtape rapper. Dukes got his first credit on a hit when Boi-1da sampled one of Dukes’ tracks for Drake’s 2014 single “0 To 100,” which peaked at #35. Great song.

From there, Frank Dukes worked on more Drake songs, as well as tracks from people like Post Malone, Rihanna, J. Cole, and Frank Ocean. He co-produced Lorde’s “Green Light,” which is cool. (That song peaked at #19.) We’ll see his work in this column again. Eventually, Dukes became the main producer on Camila Cabello’s debut album Camila. Cabello was spending studio time with lots of flashy pop producers, but Dukes’ approach was more laid-back. She liked that. At some point, Dukes played Cabello an instrumental driven by clave percussion and salsa-style piano. The track reminded Cabello of the city where she was born, and she wrote the “Havana” hook on the spot.

That’s the story that appeared in The New York Times, anyway. Maybe it’s totally accurate. But lots and lots of other people came in to help write “Havana.” One of the credited writers is former Number Ones artist Pharrell, who came in to add ad-libbed vocals. He’s the one doing the heys and grunts on the intro. Did Pharrell get a songwriting credit just for those ad-libs? I have no idea. The list also includes Ali Tamposi, who’s been in this column for working on Kelly Clarkson’s “Stronger (What Doesn’t Kill You),” and Louis Bell, who was just in this column for Post Malone’s “Rockstar.”

From what I can tell, a bunch of those people were part of a little songwriting crew that worked together all the time. Ali Tamposi and Louis Bell were in it, and they probably still are. So was Andrew Watt, a guitarist from Long Island who got his start leading California Breed, a rock band whose other members were all sons of famous classic rockers. These days, Watt is the go-to guy for aging rock stars — the Rolling Stones, Ozzy Osborne, Pearl Jam, Iggy Pop — making shiny new records. Watt was already doing some of that stuff in 2017, but he was also working with pop-star types like Post Malone and Justin Bieber. His name will be in this column again, too. So will Brian Lee — not the fake Undertaker from the early-’90s WWF, but a classically trained Queens musician who’d already co-written songs like Fifth Harmony’s “Work From Home.”

This Billboard article about Ali Tamposi makes it sound like that four-person crew wrote the “Havana” hook, not Camila Cabello. Tamposi says, “[Frank Dukes] played us that piano loop, and the hook came out like it had been written before. We were singing it in the studio thinking [that] this was too easy. Camila had wanted to write a song about Havana, and East Atlanta just rhymed, which sparked the idea of getting Young Thug on there.”

“Havana” really does sound like it was written before, like it’s too easy. The central melody is so simple, so instantly familiar, that it feels like it’s been there forever. My daughter tells me that it’s one of those songs that’s basically in your head from the moment you’re born, and I get exactly what she means. Tamposi also just mentioned Young Thug, so that means it’s time for a whole ‘nother backstory. We’re about to talk about one of the greatest, most important, most prolific rappers of the past decade-plus, so I’ll try to just hit the important points to keep this already-crazy-long column from getting too much longer. But you know how I do. I can’t help myself.

Jeffery Lamar Williams II was the 10th of 11 kids in his family, and he grew up in Atlanta’s Jonesboro South housing projects. (When Thug was born, Bryan Adams’ “(Everything I Do) I Do It For You” was the #1 song in America.) Thug’s upbringing was rough and poor. He was surrounded by gangs, and his teeth came in so crooked that he would cover his mouth with his hand in photos when he was first getting famous. (He got them fixed later.) Thug got kicked out of school and sent into a juvenile-offender program when he was in sixth grade. He told Rolling Stone that it was because he got into a fight with a teacher and broke the guy’s arm. It must’ve been absolute bedlam in that sixth-grade classroom when Young Thug broke his teacher’s arm.

Like plenty of Atlanta rap figures, Young Thug came up in his city’s criminal underground. The connections that he made came back to haunt him later. By the time that he got out of his juvenile program, Thug had started to rap, and his singular style almost immediately stood out on the Atlanta underground. Starting with his 2011 mixtape I Came From Nothing, Thug rapped in a squeaky, skittering murmur-mutter that occasionally gave way to unpredictable bursts of melody.

You can hear echoes of Lil Wayne and Future in Thug’s style, but it was a wild and expressive new take on trap, and it seemed like some real outsider-art shit. When I first encountered Thug’s music, I’d sit around trying to figure out his train of thought. I could pick up threads, but I would never understand the full picture. I forget where I saw it, but my favorite Young Thug story is that someone once saw his handwritten rhyme book, and Thug didn’t put any words in it. Instead, it was just shapes and glyphs. Only Young Thug could know what Young Thug meant.

Young Thug’s freaky-ass style did not necessarily lend itself to any mainstream, be it pop or rap, but he still found boosters. Gucci Mane signed Young Thug to his 1017 Bricksquad label, and Thug celebrated by releasing the 2013 mixtape 1017 Thug. I think that was the first one I heard, but Thug released a lot of mixtapes back then. He also signed a lot of contracts. Eventually, Thug’s label situation was such a legal tangle, with so many parties fighting over him, that he had a hard time legitimately releasing music. He figured it out, though.

Weird as his sound might’ve been, Young Thug had a tremendous, crackling energy around him. That electricity came through in his voice. You couldn’t always understand what he was saying, but his sideways hooks sunk in. In 2014, Young Thug crashed the Hot 100 for the first time when his single “Stoner” reached #47. Thug guested on moderate hits from people like T.I. and Tyga, and he teamed up with the late Rich Homie Quan, another ascendant Atlanta rapper, to release the classic 2014 mixtape Rich Gang: Tha Tour Pt. 1. It’s one of the best rap albums of this century, despite not actually being an official album. Thug and Rich Homie also reached #16 with their momentous collaboration “Lifestyle,” officially credited to Birdman’s Rich Gang entity. What a song.

Young Thug’s career was as chaotic as his music. He got into a brief but bitter feud with Lil Wayne, and he quickly fell out with Rich Homie Quan, robbing us of a Rich Gang: Tha Tour Pt. 2. But Thug’s mercurial tendencies were crucial to his art, and they led to some truly provocative moments. Thug always carried himself in ways that ran counter to rap masculinity, and he earned himself a whole lot of attention by wearing a frilly designer dress on the cover of his 2016 mixtape Jeffrey. I wrote so much stuff about Young Thug during that stretch. He was a magnetic figure, a transformative force. The younger rap stars who arrived during that period, the Lil Uzi Verts and Playboi Cartis of the world, all initially came off as Young Thug acolytes.

Young Thug mattered, but he wasn’t a pop star — not yet, anyway. His commercial mixtapes regularly debuted high on the album charts, and his singles sometimes went gold, but he wasn’t exactly making radio-friendly music. He’d pop up on tracks with people like Rae Sremmurd or Travis Scott or even post-peak Usher, but it wouldn’t have made sense to put him on, say, a Katy Perry song. When rappers appeared on mainstream pop songs, it was usually to offer a quick burst of energy or menace or horniness. That wasn’t really how Young Thug worked. I wonder if he got the “Havana” look just because the word “Havana” almost rhymes with “East Atlanta” and because Gucci Mane, the East Atlanta Santa, had just been on a Fifth Harmony song.

Jesus Christ, I haven’t even mentioned all the “Havana” songwriters yet. Also on the list is Kaan Gunesberk, a Frank Dukes associate who played keyboard on the track, and Brittany Hazzard, the Delaware-born artist and songwriter who goes by the name Starrah. Starrah works on big pop records, and we’ll see her in this column again, but she started out helping write songs for rappers like Kevin Gates and Travis Scott. My understanding is that she helps rappers come up with melodic hooks that they can sing themselves. She also makes her own music, and there’s a big of Young Thug sensibility to it.

So all these people have a hand in “Havana,” a song that’s not really about anything. Camila Cabello sings that half of her heart is in Havana ooh-na-na but that some guy took her back to East Atlanta ooh-na-na. This man ropes her in with his charm, and she seems to feel fondly about him even though she’s already left him. Maybe that guy is Young Thug. Thug’s verse is basically impossible to understand, but it’s also mostly about attraction: “Bump on her bumper like a traffic jam/ Hey, I was quick to pay that girl like Uncle Sam.” (That’s from Genius; I couldn’t have picked out most of those words myself.)

Really, though, “Havana” is about the sheer pleasure of hearing all these musical elements bump up against each other. That hook is so damn insidious that my brain now adds a reflexive mental “ooh-na-na” whenever I hear the word Havana. The piano sounds like a sample because it sounds classic — a suave and breezy salsa approach to meticulous 2017 popcraft. There’s just a bit of throaty rasp to Cabello’s vocal; she sounds confident. Young Thug, meanwhile, lets his voice slide in and out of pockets, dipping and weaving instinctively through this track.

It almost sounds too perfect. “Havana” is such an earworm that you can miss all the subtle ear-candy hooks threaded through the track, the little keyboard melodies that help it worm its way in there. Frank Dukes played most of the instruments, but he also brought in a bunch of his friends, including BadBadNotGood member and regular collaborator Leland Whitty, to add horns. The song’s sleekness really benefits from Young Thug’s off-kilter approach. He doesn’t sound tough, exactly, but he does sound untamed. He helps make this precision-engineered missile of a pop song sound a little more like a rough draft. Cabello tried something similar when she put Playboi Carti on her single “I Luv It” last year, but the song didn’t have the same juice, and it peaked at #81. (We’ll talk about Carti in this column eventually.)

“Havana” clicked. It capitalized on a new wave of interest in Latin pop, even if it was a total product of the mainstream American pop system. The song arrived during the summer of “Despacito,” and Camila Cabello took advantage, going so far as to release a Spanish-language remix with Daddy Yankee. The song steadily built its numbers in streaming and radio play, and it got a boost when the big-budget video came out in October. Music-video OG Dave Meyers directed the “Havana” video, which is probably too complicated for its own good but which I thought was cute at the time.

The “Havana” video opens with a near-endless comedy-sketch intro. Its version of Camila Cabello isn’t the glamorous one that we know from Fifth Harmony — not immediately, anyway. Instead, she’s Karla, a shy girl who watches telenovelas at home with her grandmother when she should be out finding love. But then she goes to the movies and sees the other Camila onscreen, and they get into an argument over how she should conduct her life. Social-media star Lele Pons plays Cabello’s sister, while future Netflix teen-movie hunk Noah Centineo is her love interest. The comedy is gratingly broad, and the “to all the Dreamers” dedication seems forced if well-intentioned. But Cabello is a fun presence. She looks like a star. The “Havana” clip won Video Of The Year at the 2018 VMAs, if that means anything. It’s got more than a billion views now.

“Havana” finally pushed its way to #1, interrupting the long reign of Ed Sheeran’s “Perfect,” the week that the Camila album came out. The album mostly sticks to the quasi-Latin feel of “Havana,” and it’s not a bad record, even if none of the other songs are that immediate. The album doesn’t do nearly enough to answer the question of who Camila Cabello is. Instead, it’s an old-school big-deal pop debut where almost every song sounds like a potential single. One of those songs did become an actual hit: the churning electro-ballad “Never Be The Same,” which climbed as high as #6. (It’s a 7.)

Camila went platinum, and the “Havana” single reached diamond status in 2021. This was a great start, but Camila Cabello has consistently struggled to define herself throughout her career. She often sounds like she’s chasing trends and she’s one step behind. But “Havana” wasn’t her last hit. We’ll see Cabello in this column again. We’ll see Young Thug, too.

GRADE: 8/10