Taylor Swift’s ‘Midnights’ Was A Mastermind Move Back Into Mainstream Pop

(Editor’s note: This piece was published prior to the 2024 Grammy Awards ceremony. Swift ended up taking home the Grammy for Album of the Year for ‘Midnights.’)

When Taylor Swift returned to the stage of the MTV Video Music Awards in the summer of 2022, it was clear she came with a mission. Although, at the time, many didn’t know what it would be. Her crystal chain dress had fans convinced that it was finally time for Reputation (Taylor’s Version) — a fitting return to the place that had been the origin point for all that drama. Yet, the pop star had other plans.

While accepting the award for Video Of The Year for her “All Too Well” short film, Swift revealed that she wasn’t putting out a re-recording at all. Over the past few years, she has been working to regain control of her original first six albums, of which only two more are left. Instead, she would be dropping her tenth studio album, Midnights, just a few months later.

During the pandemic, Swift’s surprise releases of Folklore and its sister project, Evermore, allowed new audiences to discover just how strong of a songwriter she was. By leaning into the inspiration of The National (who appeared on “Coney Island”) and the rise of Phoebe Bridgers-esque songwriters, she was able to tap into a vulnerable and seemingly fictitious level of creativity. Because of this new influence and shift in the culture, it’s no surprise that Bridgers would also go on to collaborate with Swift on “Nothing New.”

Although she had put out Fearless (Taylor’s Version) and Red (Taylor’s Version) in 2021, Swift needed a bridge to lift the energy from her past non-re-recorded albums. Before she announced the Eras Tour, fans had wondered how she would tour for two slow and somber albums, while also somehow incorporating the bubblegum energy that fueled 2019’s Lover — as her “Lover Fest” shows scheduled in 2020 were subsequently canceled.

Midnights was the answer to this problem. Described initially as “13 sleepless nights scattered throughout [her] life,” Swift utilized the growth she had as a songwriter during quarantine to apply it to darker pop melodies. Lyrically, she added that she viewed the record as “a collage of intensity, highs and lows and ebbs and flows.”

It prompted some of Swift’s most heartbreaking tracks, whether she took listeners through an isolating journey on “You’re On Your Own, Kid,” a track five pick that rivals the Red era, or found herself grappling with the loss of innocence on the 3 a.m. Deluxe Edition’s “Would’ve, Could’ve, Should’ve.” Yet, as promised, it also provides moments of respite through the romantic highs of “Paris” and the standard version’s closer, “Mastermind.”

Swift also directed the music videos for “Lavender Haze,” “Karma,” “Bejeweled,” and the “Anti-Hero” lead single, continuing to grow in her relatively recent artistic medium from behind the camera, of which she tested the waters as a solo director with 2019’s “The Man.”

For most artists, it is rare to put out arguably their best work sixteen years in and ten records later. But it’s become clear that Swift does not fall into the rules placed upon most artists.

Commercially, it also is Swift’s most successful era to date. She became the first artist to take up all top ten spots on the Billboard Hot 100 with songs from it. At the time, she beat her own record from 2017’s Reputation for the biggest US sales week in only four days. And it is up for six awards at this year’s Grammy Awards.

Midnights is in the running for Best Pop Vocal Album, “Anti-Hero” for Song Of The Year, Record Of The Year, and Best Pop Solo Performance, “Karma” for Best Pop Duo/Group Performance, and the coveted Album Of The Year. If Swift nabs a win for the latter, she would be the only performer (non-engineer) to take home the title four times. She is currently tied at three as the only woman, alongside Frank Sinatra, Stevie Wonder, and Paul Simon.

Considering Swift soared to new heights in 2023, it will be a question of whether the Recording Academy voters will continue to let everything she touches turn to gold. Even when looking at some of the other categories, it seems Swift’s influence has shined through.

Although they would have made it on their own otherwise, considering their individual waves last year, it is worth noting that two of the Best New Artist nominees received at least some sort of boost from being in the pop star’s orbit. Ice Spice appeared as a feature on Swift’s “Karma” remix, as the two performed it during one of the New Jersey Eras dates. This move also allowed Swift to keep Midnights in people’s minds months after its initial release. Gracie Abrams, who is also in the running, was among the tour’s opening acts.

And no matter how you might feel about it, Swift, and The Eras Tour, were inescapable this past year. Kicking off in March, Swift’s show devoted segments to each of her albums (except for her 2006 debut), as she played for three hours nightly. She creatively opened the show with selections from Lover, then Midnights as the grand finale, allowing for a perfect pop sandwich, if you will. The highest highs of 1989 and Red arrived in the middle, and then fans could take a breather during her quieter moments.

After the North American leg alone, Swift’s tour was well on track to become the first to generate over $1 billion, with even more shows scheduled in Europe this year. Her new relationship with football star Travis Kelce has placed her in direct eyesight of sports fans with each Chiefs game appearance. Swift has embraced the rise in attention — even accepting the cover award for Time’s Person Of The Year in the process.

The shift is such a stark contrast to the years she spent shying away from public outings, and instead feels like a return-to-form that was last truly present during 1989. And a lot has changed in the culture since 2014. With the rise of TikTok, Swift leaned into it for Midnights, allowing her to continue to reach new, younger listeners, and re-introduce her pop side to those who were tuned out during the Reputation, and even Lover, eras. In a sense, the album is a blend of the two.

Now that Swift’s contract allows her ownership of all master recordings, she has also moved away from the traditional album cycle. Instead, she releases what she wants, when she wants. When some demos from the Lover era leaked, she gave fans a studio version of one with “All Of The Girls You Loved Before.” And months after the Midnights release, she reignited the excitement by putting “You’re Losing Me” out on a show-exclusive CD in May 2023, leaving the rest of the fans using shared files to play the Joe Alwyn breakup anthem on repeat. Swift did not put the song on streaming until November.

It’s this free-flowing nature of Swift’s release schedule that has fueled the intensity for fans to try to find any theories or easter eggs to what might come next. Are we still in the Midnights era? Or, most recently, does Swift’s inner circle having B&W profile pics signify that it’s time for the Reputation re-recording?

This non-chronological form has worked out in Swift’s favor, particularly when it comes to sales. In the case of “You’re Losing Me,” fans first had to buy a ticket to The Eras Tour, be at a show where the CD was sold, and then buy that. And for the initial release of Midnights, the back covers formed a clock, so many opted to purchase all four — and the shelves the vinyl copies could rest on.

Swift has also seemingly recognized that no matter what she puts out, the majority of fans will now buy, without her needing to do much. Since she has been on tour, save for the Time cover, the release of Midnights saw her last few promotional appearances.

“I’m beside myself,” Swift told Jimmy Fallon on The Tonight Show after he pointed out that she broke Spotify’s record for the most-streamed album in a single day. “I’m feeling very overwhelmed by the fans’ love for the record. I’m 32 so we’re considered geriatric pop stars. So I’m just happy to be here.” (She would later beat her own record with 1989 (Taylor’s Version) — without any additional music videos or late-night interviews.)

Even if Swift does not happen to take home the Album Of The Year Grammy for Midnights, this era served as more concrete proof that she could play by her own rules and still be wildly successful, now that the perceived barriers that were present for pop stars during the early aughts have been practically knocked down. Or, who knows, she just might have another trick up her sleeve and ready to go.