Taylor Swift’s ‘Anti-Hero’ and ‘Cruel Summer’: How the Superstar Had the Feel-Cruel Hits of the Summer and Winter, Too

“Summer’s lease hath all too short a date,” wrote William Shakespeare in one of his sonnets. Well, Bill, you might be enchanted to meet Taylor Swift, who has been busy proving just how long a summer can last: four years and counting, in the case of “Cruel Summer.” The song was released in 2019 but didn’t become a smash until 2023, when by popular acclamation her quasi-oldie was all but officially declared the song of summer. (“What’s past is prologue,” indeed!)

The remarkable comeback of “Cruel Summer” was hardly the only major story as Swift singles went in 2023. Going back into the darker months, “Anti-Hero” was arguably the song of the winter — and the one that reestablished Swift’s supremacy at radio. Prior to the arrival of the “Midnights” album late in 2022, there was a period of years in which it was assumed that, as massive as she would always be as a seller and a streamer, she might have graduated past the point of having strings of No. 1 radio singles. Then, faster than you could say “Hi, it’s me — I’m the solution, it’s me,” she reclaimed her dominance of the airwaves, even before the “Eras” tour became the pop-culture phenomenon of this particular era.

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Ironically, the folk-ish twin albums she released in 2020, which were hardly built to chase airplay, helped set the ground for the 2022-23 songs that became airplay smashes, says Sean Ross, author of the industry newsletter “Ross on Radio.” If that sounds counterintuitive, let him explain: “The Americana albums helped re-set the relationship with pop radio. ‘Cardigan’ and ‘Willow’ weren’t obvious radio records, so when they went Top 20 it exceeded expectations in the way that the previous ‘Lover’ singles [‘Me’ and ‘You Need to Calm down’] did not,” Ross says. Then, when she made more of a pure pop bid again starting in October of last year, “the ‘Midnights’ songs had the advantage of being the radio-friendly records people liked from her, but informed by the changes she had been through as a songwriter and with that additional hipness.”

“Anti-Hero,” the first single out of the gate from “Midnights,” was a perfect storm: Sonically, her collaboration with Jack Antonoff sounded utterly familiar to anyone who had pined for a return to electro-pop during her Year of Living Acoustically… yet lyrically, it was self-effacing to the point of being strange, and also funny, in a fashion that made it the most deeply quotable smash of this or any recent season. (Who could have guessed that “I’m the problem” would be the angst-ridden line that Swifties would enjoy shouting back more than almost any other on tour?) Swift and Antonoff have said that achieving an across-the-board No. 1 was the furthest thing from their minds when they were crafting this oddball number. But radio was clearly in her sights by the time she and Republic Records brought it to market. Swift “still cares about radio,” Ross says. “In the BTS era, it would have been easy to let the fans do all the work, and yet radio premieres were still part of the initial splash for ‘Midnights,'” with Swift sharing her thoughts about the songs in specials provided to stations.

And then the “Lover” album, which had proven less than an all-consuming monster at radio, came back from the dead, in the form of the happy revivification of “Cruel Summer.” The song had been pegged to be the third single off “Lover” for the summer of 2020, before COVID scotched that plan (not least of all because the title would have been way too on the nose) and she made her pandemic pivot to woodsiness. Swifties considered it not just a lost opportunity but one that needed to be rectified, and they lobbied for the song to get its due three summers later. Swift has said that the song’s mixed moods describe “how oftentimes a summer romance can be layered with all these feelings of, like, pining away and sometimes secrecy” — meaning that young listeners could find something to identify with it it whether they were madly in love or feeling thwarted in a relationship going wrong.

In March, Swift kicked off her stadium tour, and what was at the very top of the three-and-a-half-hour set? Well, a very tiny snippet of “Miss Americana and the Heartbreak Prince,” but after that tease, the real start of the show was “Cruel Summer.” It was if Swift had sent out a bat-signal to her fans by placing the underdog song in that pole position. In early June, the song suddenly made a streaming-driven reappearance on the Hot 100. On June 15, Republic announced that “Cruel Summer” was going to pop radio — even though the designated radio single of the moment, “Karma,” from “Midnights,” was still on the rise. (“Karma” didn’t exactly get squelched, in the self-competition; that single made it to No. 2.) “Cruel Summer” entered the Top 10 in July and finally reached No. 1 on Oct. 23, making the final leap with the help of “Eras Tour” movie mania.

How much of the “Cruel” comeback story was organic and driven by pure Swiftie sentiment, and how much was it Swift being, you know, a mastermind? Seizing the opportunity presented by its virality is probably the best explanation, because rarely, if ever, does a label have as part of a master plan pushing two singles to radio at once. So maybe this is the best way of thinking about “Cruel Summer”: It just had good karma.

SONGWRITERS: St. Vincent, Jack Antonoff, Taylor Swift

PRODUCERS: Taylor Swift, Jack Antonoff

LABEL: Republic

HITMAKERS:

Jack Antonoff, producer and songwriter

Jim Roppo, co-president, Republic Records

Kevin Lipson, executive VP, global commerce & digital strategy, Republic Records

Gary Spangler, executive VP, Republic Records

13 Management

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