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 trumped 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’s hit 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.