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.
So it begins. Except not really. By the time she finally landed her first #1 hit on the Billboard Hot 100, Taylor Swift had been circling that top spot for years, getting close to snatching it more than once. From the moment that she first arrived as a starry-eyed teenage country singer, Swift was a very big deal. She sold millions of records, toured arenas and then stadiums, and challenged Dolly Parton for the role of the biggest, most impactful pop crossover artist in the history of country music. She’d won her first Grammy for Album Of The Year, and she’d become a point of national conversation. As far as I can tell, the only thing working against Swift was this: She was a country artist, and at that time, country artists didn’t score #1 hits on the pop chart. So Swift made a move that was both brave and obvious: She stopped being a country artist.
Taylor Swift was always going to reach #1. It was inevitable. When Swift first arrived, I couldn’t have predicted that she’d become the most famous human being on the planet, which is probably what she is right now. But I definitely could’ve told you that she would make hits. By the time she turned toward full-on pop music, you could make a truly awesome greatest-hits album drawn from nothing but her first three studio LPs and the loose tracks that she cranked out with terrifying regularity. As such, Swift’s first #1 hit was almost a formality.
But Taylor Swift’s first #1 hit was also a departure. It was the moment that Swift stepped outside the bounds of the Nashville studio system that nurtured her, turning instead toward the king of mechanized crossover uber-pop. The first single from Red, Swift’s fourth album, would’ve probably gone to #1 just by virtue of being the first single on the new Taylor Swift album. But Swift wasn’t taking any chances. Swift might be the canniest operator in pop history. She seeded the ground for her big pop-crossover moment, and she didn’t exactly shock the world by deciding to work with Max Martin. With that decision, though, Swift consciously turned her music into something bigger, brighter, and brattier. The resulting song isn’t anywhere near her best, but it’s still a major turning point in one of the biggest careers in pop history.
Taylor Swift is going to be in this column so many times, and we’ll have to approach her discography in a sort of chronologically jangled Pulp Fiction way because of the way that she’s commercially weaponized her own backstory. The story and the songs play into one another, as she’s always used her own public coming-of-age milestones as raw material for gigantic songs. But I can’t emphasize this point enough: By the time she started landing #1 hits, Swift was already a fully formed pop titan. Kanye West once bragged, on record, that he made Taylor Swift famous, and the moment when he interrupted her VMA acceptance speech was definitely the most high-profile thing that had happened in her run to that point. But when he shoved his way into her life, Taylor Swift was already selling more records than Kanye West.
At this point, whenever you tell Swift’s story, it feels like pieces falling into place. Every new development feels inevitable, as if her dominance was written in the stars. That’s never how it is with pop stardom, of course. It’s an utterly randomized lottery system, especially when your parents’ names don’t show up in blue on your Wikipedia page. But even without famous parents or a background in children’s television, Swift’s road was smoother than most.
Taylor Alison Swift grew up on a Christmas tree farm in Pennsylvania, about an hour outside of Philadelphia. (When Swift was born, Billy Joel’s “We Didn’t Start The Fire” was the #1 song in America.) Swift’s family was well-off; her father worked as a stockbroker at Merill Lynch. They were also musically inclined. Swift’s grandmother was once an opera singer, and her parents named her after former Number Ones artist James Taylor. When Swift showed interest in a musical career from a very young age, her parents had the means and the inclination to help make it happen.
When Taylor Swift was nine years old, she started acting in musicals and taking voice and acting lessons in New York. She loved country music, and she figured out early on that she had to be in Nashville if she wanted to do anything in that world. When Swift was 11, she recorded a demo CD — karaoke versions of Dixie Chicks and Shania Twain songs — and got her mother to take her to Nashville and drive her around to different labels, where she walked in and handed her CD to receptionists. When that didn’t immediately land her a record deal, Swift learned how to play guitar and started writing her own songs. She was 13 when she found a manager and started playing showcases, and she was 14 when her father transferred to the Merill Lynch Nashville office and moved the whole family down there.
At 13, Taylor Swift signed a development deal with RCA, and she started working with big-deal Nashville songwriters. Swift also signed a big publishing deal, and when she got the idea that RCA wasn’t interested in her songwriting and that she wasn’t a priority, she walked away from the label. In 2005, a longtime Nashville music exec named Scott Borchetta saw Swift play a showcase at the storied Bluebird Café. Borchetta was in the process of leaving Universal and starting Big Machine Records, his own label, and he signed Swift when she was 15. Swift was one of the first artists signed to Big Machine, and her father invested in the startup label, buying three percent of the company. Big Machine eventually became a huge player in Nashville, mostly because of how well Swift’s records sold.
Taylor Swift’s debut single “Tim McGraw” came out in 2006, when she was 16. It’s a truly great song, a sign that Swift was already something special. On “Tim McGraw,” written with Swift’s longtime collaborator Liz Rose, Swift was able to describe the rush of young love and the sad warmth of its absence. It’s also a song about pop music — about the way that certain songs can always sweep you right back to where you were when you first heard them. I can vividly remember watching Swift play “Tim McGraw” at the ACM Awards and then walking down to the front row and introducing herself to McGraw — a perfectly-orchestrated meet-cute. McGraw later became her labelmate at Big Machine. (Tim McGraw’s highest-charting Hot 100 hit as lead artist is “It’s Your Love,” a 1997 duet with his wife Faith Hill, which peaked at #7. It’s a 6. McGraw also made it to #3 as a guest on Nelly’s 2004 single “Over And Over.” That’s an 8.)
“Tim McGraw” was a top-10 country hit, and it peaked at #40 on the Hot 100 — a huge success for a young and brand-new country singer. Swift had many, many more hits where that one came from. Her self-titled debut album came out later in 2006, and “Our Song,” its third single, was Swift’s first #1 country hit. “Our Song” also reached #16 on the Hot 100, and another single, “Teardrops On My Guitar,” did even better, peaking at #13. Those are just fucking awesome songs. They’re sharp and bright and catchy and conversational, and they get at heavy feelings without overplaying them. I think the post-breakup snarl “Picture To Burn” was the one that finally convinced me to pay actual money for the Taylor Swift CD. In any case, I was on board from the jump.
Swift’s debut album spun off five singles, and all five reached the top 40 of the Hot 100. Eventually, that album sold seven million copies. Swift had tapped into something. Most of her country peers were middle-aged performers with middle-aged fanbases, but Swift discovered an overlap between country and the Radio Disney teen-pop that was doing huge numbers at the time. Swift presented herself as a country artist, complete with sometimes-overstated fake Southern accent. But she also loved emo, rap, Katy Perry-style pop maximalism, Def Leppard, ’70s singer-songwriter stuff, and Broadway balladry. You could catch little glimpses of those inspirations in her songwriting and in the ways that she presented herself to the world. She was a big deal on country radio and on MySpace, an unclaimed territory for a country singer. (It’s a bit like how Morgan Wallen, a future subject of this column, became the first country star to do huge streaming numbers.)
While promoting that first album, Taylor Swift opened for more-established country stars: Rascal Flatts, Brad Paisley, George Strait, Tim McGraw. After that, she’d never open for anyone again. She won the CMA’s Horizon Award — the country version of Best New Artist — and she was nominated for the Grammy, which she lost to Amy Winehouse. In 2008, Swift landed her first proper top-10 hit: “Change,” which eventually showed up on her sophomore album Fearless but which was originally released as some kind of AT&T promo with the Olympics. (“Change” peaked at #10. It’s an 8.)
When Fearless came out late in 2008, I was fucking gobsmacked. I’d really liked that first album, but Fearless was a giant leap in every way — a readymade greatest-hits record, from a teenager who was just on her second LP. I reviewed the album for L Magazine, a free Brooklyn weekly thing, and ended my review with this sentence: “Respect motherfucking craft when you hear it.” (I really wish that review was still online, but at least some trace evidence remains.) And Fearless turned out to be every bit as big as I expected. Its first proper single, the immortal idealized-romance classic “Love Story,” reached #4. Another, the lovestruck quasi-pop-punk tantrum-sigh “You Belong With Me,” went all the way to #2. (They’re both 10s.) And those chart numbers don’t even come close to hinting at the impact of Fearless.
The Kanye thing happened during the Fearless album cycle. Swift also embarked on her first headlining tour, where she was already at the arena level. (Justin Bieber, someone who will appear in this column a bunch of times, was one of her openers.) Fearless became the biggest seller of 2009, and it eventually went diamond. It also won the Grammy for Album Of The Year, beating out records from Lady Gaga, Beyoncé, the Black Eyed Peas, and the Dave Matthews Band. This was one of those rare cases where, at least to my mind, the Grammy voters got it right. Swift now has three of those Album Of The Year trophies, which means that she’s tied with Frank Sinatra, Paul Simon, and Stevie Wonder for the most ever. There’s a good chance that she’ll win a fourth next month.
In 2010, Taylor Swift began a pretty dire film career, making her acting debut in Valentine’s Day and reaching #2 with “Today Is A Fairytale,” a throwaway song that she contributed to its soundtrack. (It’s a 6.) Swift also started helping write singles for other artists: Boys Like Girls, Kellie Pickler, future Number Ones artist Miley Cyrus. Later that year, Swift released Speak Now, her third album. For that one, Swift wrote every song completely on her own, without co-writers. The LP sold about six million copies, and lead single “Mine” peaked at #3. (It’s a 9.) Speak Now is Swift’s last full-on country album, to the extent that any of her albums are full-on country albums. A great many of my favorite Taylor Swift songs are from that part of her career, before she started scoring proper #1 hits. Nevertheless, the writing was on the wall. Taylor Swift was already huge, but if she wanted to get any bigger, she would have to leave country behind and go pop. And Taylor Swift definitely wanted to get bigger. She probably still does.
Taylor Swift was still embedded in the country music universe when she recorded Red, and she still worked with many of her old collaborators. But Swift had the chance to work with pretty much whoever she wanted, and she took it. On Red, Swift and her label brought in tons of big-deal pop and rock producers: Jeff Bhasker, Dan Wilson, Jacknife Lee, Butch Walker. Most crucially, though, she linked up with Max Martin. Martin and his sidekick Shellback worked on three tracks from Red, and all three became big hits. Those collaborations led to a working relationship that carried through Swift’s next few records. 1989, the album after Red, is supposedly Swift’s mainstream-pop move, but when you’re making records with Max Martin, you’re already about as pop as anyone on the planet.
The Taylor Swift/Max Martin team had an interesting dynamic. Martin and Shellback are both Swedish; English is not their first language. Martin famously doesn’t put much stock in lyrics. He’ll torture language in order to make the verses fit the melodies in his head. Taylor Swift is a high-level hooksmith, as well, but she’s a lyrics-first person. Taylor Swift songs aren’t allowed to simply function as songs. They have to address where she is in her life, and they have to work within the flow of her personal narrative. (Even when Swift tells stories about characters, those stories tend to show where she is as a writer.) Those two opposite approaches could’ve made for a terrible clash, but Swift and Martin found ways to make them work together.
Case in point: “We Are Never Ever Getting Back Together,” Swift’s first Hot 100 chart-topper, does all the things that a Max Martin track is supposed to do. There’s basically no country in the song whatsoever. The track starts with an acoustic guitar, but it’s been chopped up into shards. (The guitar comes from Shellback, who also programmed the drums and played bass and keyboards. Martin played more keyboards. Nashville’s army of studio musicians was not remotely involved with the track.) The hooks are sharp and insistent and instantly memorable, but the lyrics still tell a story.
The story is a familiar one. Like plenty of Taylor Swift songs, “We Are Never Ever Getting Back Together” is about a relationship that ended not too long before Swift recorded the song. Swift never ever reveals the subjects of her songs, but general consensus is that the song is addressed to Jake Gyllenhaal, who dated Swift for a few months in 2010. Gyllenhaal is nearly a decade older than Swift, and he tends to come off as a pretentious, neglectful dickbag in Taylor Swift songs — an unfortunate reality that still dogs him today. (The Swift/Gyllenhaal relationship will eventually figure into another song in this column.) Incidentally, when Swift was recording Red, she was dating Conor Kennedy, son of current wingnut presidential candidate Robert F. Kennedy Jr. Thank god she got out of that one; nobody wants to see Taylor Swift out there looking like Cheryl Hines.
When Swift was working with Max Martin and Shellback in the studio, she ran into an acquaintance who mentioned a rumor that Swift and an ex — presumably Gyllenhaal — were getting back together. This annoyed Swift. She started telling Martin and Shellback about the relationship, which kept ending and then starting again, and they took less than half an hour to turn that into a song. Back when she was still regularly speaking to the press, Swift told USA Today that the song was her retribution against a guy who “made me feel like I wasn’t as good or as relevant as these hipster bands he listened to. So I made a song that I knew would absolutely drive him crazy when he heard it on the radio. Not only would it hopefully be played a lot, so that he’d have to hear it, but it’s the opposite of the kind of music that he was trying to make me feel inferior to.”
Taylor Swift’s line about the ex playing “some indie record that’s much cooler than mine” was funny in 2012, and it’s funnier now that Swift is regularly collaborating with the National and Bon Iver and Phoebe Bridgers and whatnot. I don’t think Taylor Swift is still getting revenge on this guy who didn’t respect motherfucking craft when he heard it, but it’s not entirely impossible. I’ve always wondered: What indie record was it? Gyllenhaal was in Vampire Weekend’s “Giving Up The Gun” video in 2010, and he took his ex Jenny Lewis to the Golden Globes shortly after he and Swift broke up, so those are two possibilities. But those are pretty entry-level, as far as indie records go. What if Jake Gyllenhaal just wouldn’t shut up about, like, Deerhoof and Xiu Xiu? What if he tried to make Taylor Swift listen to Swans? The mind reels.
“We Are Never Ever Getting Back Together” isn’t the most vicious or incisive Taylor Swift breakup song, and its big monster hooks don’t leave enough room for the finely observed storytelling details that she loves to work in. But she still gets bars off: “We hadn’t seen each other in a month when you said you needed space,” “I’m really gonna miss you picking fights and me falling for it, screaming that I’m right.” On the bridge, Swift goes into spoken-word mode, and you can hear her eyeroll when she does her durr-voice Jake Gyllenhaal impression: “I still love you.”
If Swift really intended to make an earworm that would drive Gyllenhaal nuts, then you have to imagine that she succeeded. The song has the frothy punch that nobody does like Max Martin — the insistent beat and crashing chords and doubled-up ultra-repetitive hook. It’s a perfectly sharp pop song, but it’s also lightly annoying, in an intentional way. Like a lot of first singles from Taylor Swift albums, especially the post-country ones, “We Are Never Ever Getting Back Together” sacrifices nuance for brute-force catchiness. It’s effective, but I don’t have the same affection for the track as I do for so many Swift deep cuts.
I strongly dislike the “We Are Never Ever Getting Back Together” video. Taylor Swift doesn’t exactly have a great music-video track record, but this one is worse than most of them. Director Declan Whitebloom, a past Swift collaborator, had the idea to make it a single-take video with multiple sets and costume changes, and everyone involved put serious work into making it seamless. I’m sure plenty of people saw the video and didn’t even register the lack of camera cuts. But for reasons that I cannot begin to imagine, we also get Swift’s backing-band guys mugging frantically in animal costumes — the kind of attention-grabbing twee silliness that doesn’t come close to making up for the complete lack of visual style. (Big-deal male model Noah Mills plays the ex.)
But a weak video was never going to stop “We Are Never Ever Getting Back Together.” The song came out two months before the Red album, and it debuted at #72 on the Hot 100 based on nothing more than a couple of days of radio play. The next week, the song sold hundreds of thousands of downloads, and it vaulted straight to #1. By some metrics, this was the beginning of a very, very long imperial era for Taylor Swift. The song is nakedly pop — a clear sign that Swift was rejecting country radio — but country radio didn’t reject her back at first. Big Machine released a “country mix” of the song that wasn’t fooling anyone, and it became Swift’s last #1 hit on Billboard‘s Hot Country Songs chart. (That’s a little illusory, since Billboard had just started to factor downloads into that chart. On Country Airplay, the song peaked at #13. Still, country radio stations were playing a song that was clearly not country. A couple of years later, Swift had to straight-up announce that she was done with the genre for the world to get the message.)
Around the time that “We Are Never Ever Getting Back Together” was first out, I took my daughter to this farm near my in-laws’ house in northern Virginia. It’s one of these attractions that’s mostly set up so that kids can wander around and pet goats or whatever. This day, though, they happened to have an equestrian vaulting meet. That’s the sport where you stand on horseback and kind of dance around while the horse is trotting. It looks terrifying. My kid and I watched for a while, and almost all the competitors were blonde girls in sparkly bodysuits. The last vaulter was an effeminate boy who danced to “We Are Never Ever Getting Back Together” while up on that horse, pointing in different directions during the “you go talk to your friends, talk to my friends” bit. This kid was in it, and the song seemed to be made just for him. Now, I think of him whenever I hear it.
None of the other singles from Red made it to #1 — at least on the album’s original release — but some of them came close. “I Knew You Were Trouble,” one of the other Max Martin/Shellback collaborations, peaked at #2. (It’s an 8.) I cackled so hard when I first heard that song. Suddenly, Taylor Swift was throwing dubstep bass-drops into her tracks. The audacity! I loved it. I loved the screaming-goats version even more. “22,” the album’s third Max Martin track, came out as the album’s fourth single and couldn’t make it past #20. For my money, though, that’s the best of them, and it’s one of the most deliriously fun songs that Taylor Swift ever made.
Max Martin wasn’t involved in all the hits from Red. “Begin Again,” the album’s tingly closing track, peaked at #7. If Swift ever reaches her crustcore phase, I hope she calls her band Break And Burn And End. (It’s a 7.) Swift also made it to #6 with her Red title track, which really walked the line between her pop and country sides right before those sides cleanly split. (That one is an 8.) Red ultimately sold seven million copies in the US alone. In 2012, the LP was the year’s #2 seller, right behind Adele’s 21, which held the top spot for a second straight year. Red also got Swift her second nomination for the Album Of The Year Grammy, but she lost that one to Daft Punk’s Random Access Memories. (Swift and Daft Punk played maybe the two best stadium shows I’ve ever seen, but we don’t get too many other opportunities to put them in direct competition with one another.)
Nine years after Red first came out, Taylor Swift released her re-recorded version of that album. We’ll eventually get deeper into the wildly successful Taylor’s Version gambit, but it was trippy to hear a take on “We Are Never Ever Getting Back Together” that was nearly identical but without the same euphoric in-the-moment anger. Shellback participated in the re-recorded version of that song, but Max Martin did not, and the track was probably missing something without him. The Taylor’s Version of “We Are Never Getting Back Together” wasn’t a big hit; it peaked at #55. But the song did what it needed to do in 2012. It got Swift a #1 pop hit. We’ll see many more Taylor Swift songs, including a different re-recorded Red track, in this column.
BONUS BEATS: Here’s Fifth Harmony performing a slightly awkward version of “We Are Never Ever Getting Back Together” in 2012, when they were still contestants on The X Factor:
(Fifth Harmony’s highest-charting single, the 2016 Ty Dolla $ign collab “Work From Home,” peaked at #4. It’s a 10. Future Taylor Swift tourmate Camila Cabello will eventually appear in this column.)
BONUS BONUS BEATS: Here’s Jimmy Eat World covering “We Are Never Ever Getting Back Together” as an online bonus while doing musical-guest duties on a 2013 episode of Conan:
BONUS BONUS BONUS BEATS: Here’s Wild Pink, a band I really like, doing a version of “We Are Never Ever Getting Back Together” for ReRed, a 2019 compilation that’s nothing but cooler-than-mine indie types covering songs from Red:
The Number Ones: Twenty Chart-Topping Hits That Reveal The History Of Pop Music is out now on paperback via Hachette Books. Buy it here, or else hide away and find your peace of mind with some small-press book that’s much cooler than mine.