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How Taylor Swift Beat Sinatra

Taylor Swift launched the Midnights era at an awards show, announcing her tenth album during the 2022 VMAs. Maybe it was fate that she ended it at another, the Grammys, where she won her fourth Album of the Year trophy and kicked off her next release, The Tortured Poets Department. With her win for Midnights, Swift broke a four-way tie with Frank Sinatra, Stevie Wonder, and Paul Simon to become the artist with the most AOTY wins. This means 40 percent of her albums have been recognized by her peers as the year’s best: Fearless at the 2010 Grammys, 1989 in 2016, folklore in 2021, and now Midnights.

While it’s hard to call Swift’s first-place finish an outright shock — Midnights was a wildly successful album buoyed by a just-as-successful tour while Swift dominated over a year of conversation — it’s surprising to see her break a Grammys record so handily and to do it over competition like the night’s top nominee, SZA, who was up for her second album, SOS. Here’s how Swift pulled it off.

She wasn’t just successful — she gave the music industry hope.

Prior to October 2022, most industry observers thought a million-album week on “The Billboard 200” (a number combining album sales, song sales, and an equivalent amount of streams) was no longer attainable in today’s streaming economy. Adele couldn’t do it, Drake couldn’t do it, and successful newcomers like Morgan Wallen and Bad Bunny couldn’t do it. Then Midnights posted a stunning 1.5 million units, the first seven-figure American debut since Swift’s own reputation in 2017 (and since Billboard tightened up its bundling rules). As the music industry became even more resigned to streaming’s dominance, there was Swift, doing the impossible. For good measure, she did it again with 1989 (Taylor’s Version) last fall.

It’s still up for debate whether a musician not named Taylor Swift could replicate the feat, but she has given her peers reason to try. And she followed that up with one of the most successful tours of all time, headlining the post-COVID concert awakening we had been promised for years. With the Eras Tour, she let many other artists share in that success, giving a slew of rising singers their biggest stage yet.

It was always going to take a massive release for Swift to win her fourth AOTY. Sinatra won all three of his trophies when he was past his prime; Wonder’s output never returned to his classic-era heights after his third winner, Songs in the Key of Life; and Simon won his third only by finding solo acclaim with Graceland. But Swift didn’t just best herself with Midnights — she elevated the entire music industry, which would have been pretty hard for the Recording Academy to ignore.

She’s an albums artist.

After “Anti-Hero” became Swift’s most successful single ever, I wondered if this would finally be the year she won a top-song Grammy (she has lost five times for Record of the Year and seven for Song of the Year). But at the end of the day, Midnights ******* it (and the post-committee Academy just doesn’t do sweeps anymore). Unlike, say, Miley Cyrus, who won Record of the Year for “Flowers,” Swift’***** song never felt bigger than the album it was on. Since she won her first AOTY for Fearless, Swift has made capital-A albums, cohesive musical thoughts. (Midnights’ AOTY was only her 14th Grammy, but half of those have been album awards.) She only strengthened that argument with the Eras Tour, a three-plus-hour reminder of how much detail she puts into each project. Even if the world mostly forgot that Swift had introduced Midnights as a concept album, it’s still a holistic work in sound and theme. She also kept a close circle while making it, working with only a few co-writers and co-producing every track with Jack Antonoff. In other words, Midnights fit older voters’ expectations of what an album ought to be, too.

She held on to her new folklore fans.

In such a plural Academy, your own genre alone can’t carry you to AOTY. That’s how Jon Batiste surprised for We Are back in 2022, with nominations across R&B, American roots, and contemporary-classical categories (plus jazz for Soul). Swift last won AOTY for 2020’s folklore, an ostensibly pop album that drew on folk and country and was largely produced by the National’s Aaron Dessner, a rock musician. From the way her peers heaped praise on that album, it seemed as if she’d stacked votes from all those corners of the Academy to come out on top.

Midnights is a return to much more straightforward pop for Swift, and she isn’t working with Dessner anymore. But I assume she still earned sizable support from rock, alternative, and country voters. After folklore made it cool to like Swift again, that didn’t stop with Midnights, an album that has been publicly praised by everyone from Keith Urban to Flavor Flav. Even two of her fellow AOTY nominees, boygenius and Lana Del Rey, had direct ties to Swift, and some of their would-be voters probably swung her way instead.

She had key technical voters’ support.

Swift may now have the most AOTY wins among artists, but someone else still beats her outright: Serban Ghenea, an audio engineer who has worked with Swift since Red. He may be one of the most respected collaborators in pop right now, and this was his own fifth AOTY win (he has also won for Adele’s 25 and Bruno Mars’s 24K Magic). The Academy is full of people like Ghenea — the engineers, writers, and producers often standing behind an artist when they win — and if you want to win big, you’ve got to earn their votes. Swift has. It’s not just the engineers, either, since Antonoff, her right hand, once again cleaned up in Producer of the Year.

This is where a competitor like SZA came up short. Ghenea may have mixed a few of the tracks on SOS, but on the whole, SZA’s album eschewed well-regarded, big-name technicians. That’s not to say it wasn’t well produced or written, or that SZA didn’t work with good collaborators — it just doesn’t get you noticed at the Grammys.

She’s Taylor Swift.

Whenever Swift attends an awards show these days, her peers turn into fans. Everyone’s clamoring for a photo with her, and people shout her out when accepting trophies that have nothing to do with her. She’s like the music world’s Meryl Streep — even when Streep is also in the room.

That continued last night when Swift reunited with old friends Dessner and Ed Sheeran, snapped pics with Jelly Roll and Kelsea Ballerini, and got an onstage mention as SZA accepted Best R&B Song. When people weren’t trying to meet Swift, she was up singing and dancing to their music — from Tracy Chapman’s to Olivia Rodrigo’s. Okay, yes, maybe you’re a bit tired of Swift at this point, but few in that room appeared to be.

And while Swift had quality AOTY competition, she still towers over it as a star. Most of the other nominees are much earlier in their careers than she is, and none comes close to her level of fame — no Adele, no Beyoncé, no Ariana. To many in that room, she’s both a hero and their biggest competition — the rare living legend who’s still writing their story.

Does this mean we’re entering an era when every new Swift album will be an AOTY lock? I continue to be wrong about her Grammy prospects, but still I’m not sure. Her past AOTY follow-ups, Speak Now and reputation, were snubbed for the top nominations; evermore’s nod for AOTY was its only one that year. And The Tortured Poets Department won’t just be following up Midnights — by releasing the album in April, Swift is setting it up to compete at next year’s awards. Just two artists have won AOTY at back-to-back ceremonies, and no artist has done it in nearly 50 years. (Frank Sinatra did in 1966 and ’67, Stevie Wonder in 1974 and ’75.) Barring a catastrophe, Tortured Poets will certainly be nominated, but I could see voters feeling as though Swift’s history-making fourth win was enough and deciding to make room for someone else. If anyone can overcome more impossible odds to make more Grammys history, though, it’ll be Swift.


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