From Deep Cut to Hot 100 Hit

Almost every Taylor Swift album includes a song adored by fans that, for whatever reason, never gets released as a single. On 2012’s Red, it was the wounded breakup ballad “All Too Well.” On 2017’s Reputation, it was the exhilarating, bittersweet “Getaway Car.” And on 2019’s Lover, it was the hurts-so-good romantic anthem “Cruel Summer,” which Swift wrote with longtime collaborator Jack Antonoff and art-pop auteur St. Vincent.

Swifties ride hard for their favorite deep cuts to get selected as singles. But the reaction to “Cruel Summer” felt different, ranging from the fantastical to the sweetly deranged. What was it about this neon-toned synth-pop track that resonated more than others? It could have been anything from “This song is so good it HAS to be known by the general public” to “Taylor deserves to top the Hot 100 in perpetuity”–type hyperbole. Most likely, though, it was a feeling that Swift’s image was still slightly dinged after the fallout from the 1989 era, and that the singles released from Lover — including “ME!” and “You Need to Calm Down” — weren’t as representative of Swift’s seventh album or her sharp songwriting skills. “Cruel Summer,” with its empathetic narrative, anthemic chorus, and dazzling bridge, was.

This June, Swift finally granted her fans’ wishes and released the four-year-old song as a single, even as she was in the midst of promoting Speak Now (Taylor’s Version) and a deluxe edition of Midnights. Despite its straightforward pop credentials, the track’s journey to getting an official release is an unusually twisty one — a slow-burn success story that involves an indie-rock icon, Ellen DeGeneres, and a royalty dispute. Now, “Cruel Summer” is shaping up to be Swift’s biggest hit of the year, having landed in the Hot 100 top five. Ahead, a full recounting of the long road to “Cruel Summer” singledom.

July 2011: Nearly a decade before they would write a charting hit together,
Annie Clark meets Taylor Swift for the first time backstage at one of the Newark stops on Swift’s 2011 Speak Now tour. Clark is two albums into her career at this point, a few months off from releasing her darkly toned career high Strange Mercy; upon being told that Clark is a musician too, Swift provides some words of encouragement: “That’s great! Good luck with everything.”

October 14, 2014: Swift releases “Out of the Woods,” a promotional single for her fifth album, the synth-pop pivot 1989. She’ll later say that this track, which is basically one long build to a colossal bridge, provided a blueprint for “Cruel Summer.” (Since the beginning of her career, Swift has been known for her sharp and incredibly dynamic bridges, to the point that ranking them has become a favored pastime for fans and music outlets alike.)

August 25, 2015: Swift brings Clark onstage during the guest-heavy 1989 tour for a performance of “Dreams,” Clark’s recent collaboration with Beck. This is the first time Clark and Swift collaborate.

May 2, 2016: Swift meets Joe Alwyn, widely understood to be the subject of “Cruel Summer,” at the Met Gala. At this point, she’s dating Calvin Harris and is about to be briefly linked to Tom Hiddleston; the song “Dress,” from Reputation, alludes to this first meeting.

November 10, 2017: Swift releases Reputation, her sixth album. The song “Getaway Car” plays like a spiritual successor to “Out of the Woods” and is later recognized by fans as a clear antecedent to “Cruel Summer.”

November 21, 2018: Swift wraps up the world tour in support of Reputation with a sold-out show at the 50,000-capacity Tokyo Dome. Swift credits the tour with having “assign[ed] humanity” to her life and art —reminding her that, despite beef and backlash having changed the trajectory of her career, she still had fans who would treat her like a real person. This realization sparks a desire to write an album that’s more open and vulnerable than the steely Reputation.

June 13, 2019: Swift announces that her seventh album, Lover, will be released on August 23. She describes the album as “very romantic,” even if sometimes that romance is found “in loneliness or sadness or going through conflict.”

June 17, 2019: Swift releases the video for “You Need to Calm Down,” her slightly confused (if decidedly camp, given its stiff attempts at using gay slang) song about LGBTQIA+ rights. In the clip, Adam Lambert can be seen giving a “Cruel Summer” tattoo to Ellen DeGeneres.

August 16, 2019: Swift releases the Lover track list; track two is “Cruel Summer.”

August 19, 2019: Swift drops an Easter egg for “Cruel Summer” in an Amazon advertisement, leading fans to think it may be a forthcoming single.

August 23, 2019: Swift releases Lover. In a session for iHeartRadio, she speaks about writing and recording “Cruel Summer” for the first — and, basically, last — time, describing it as a song about “how oftentimes a summer romance can be layered with all these feelings of, like, pining away and sometimes secrecy.” She says the song “has some of my favorite lyrics on it” and notes that Jack Antonoff and Clark produced the bulk of the track and instrumentation, while she wrote the top line. She says that for this song, she and Antonoff “revisited” the idea of a bridge being “the biggest moment of the song,” first attempted on “Out of the Woods.”

The same day, Swift surprises fans at a “Cruel Summer” promotional mural that’s been painted in Brooklyn, sparking further speculation it’s the next single. Many critics describe the track as one of Lover’s standouts: Writing for Pitchfork, Anna Gaca notes the song’s “magnetic pink glow”; NME’s Nick Levine describes it as a “brilliant pop song.”

August 31, 2019: Summer 2019 cruelly passes without Swift releasing “Cruel Summer” as a single, sending it to radio, or dropping a music video.

September 1, 2019: Lover debuts at No. 1 on the Billboard 200, becoming Swift’s sixth chart leader. “Cruel Summer” debuts at No. 29 on the Hot 100 and stays on the chart for two weeks, a placement it achieves with little to no radio support.

September 2, 2019: Swift performs Lover songs on the BBC Radio 1 Live Lounge. She doesn’t perform “Cruel Summer” — it’ll be a good three and a half years before she ever performs it live, so sit tight — but she does perform a lovely cover of Phil Collins’s “Can’t Stop Loving You.” (Not really relevant to the timeline; I just think it’s just a nice cover.)

September 9, 2019: Taylor plays a promotional concert dubbed the City of Lover concert at Paris’s storied L’Olympia venue. She runs through a lot of Lover’s lengthy track list, but omits “Cruel Summer.”

September 17, 2019: Swift announces that her Lover tour will hit North America, Europe, and Brazil in 2020, including four massive festival-style shows dubbed Lover Fest, giving fans their first opportunity to hear “Cruel Summer”’s iconic synth-burps brought to life.

January 27, 2020: Swift releases “The Man” as the fourth single from Lover, once again stiffing fans hoping that their tortured but euphoric fave “Cruel Summer” will get a music video.

April 17, 2020: Swift postpones her Lover tour due to COVID and says she won’t be making any live appearances or performances in 2020. On social media, she tells fans she’ll be “onstage as soon as I can.” Although fans don’t know it yet, this marks the end of Swift’s Lover era.

April 22, 2020: Olivia Rodrigo, the plucky young star of the Disney show High School Musical: The Musical: The Series, covers “Cruel Summer” during an MTV at-home performance, thus marking the beginning of Rodrigo’s complicated involvement with the rise and success of “Cruel Summer.” Swift praises the performance on Instagram, writing, “THE TALENT. Love This!!! Thanks for this beautiful performance @olivia.rodrigo” — leading Rodrigo to fan out on social media, writing on Instagram that Swift is “THE REASON I WRITE SONGS.” (She then proceeded to make a Punk’d reference, a nicely idiosyncratic choice for someone who was 4 when the show went off the air.)

July 23, 2020: Swift announces that her eighth album, Folklore, will be out on July 24. On release day, a tweet goes viral listing “Cruel Summer” as a member of the “best tracks that were never treated as a single” club.

August 31, 2020: Another cruel summer passes without “Cruel Summer” getting the single treatment. To be fair, this season was pretty cruel for everyone.

December 11, 2020: Swift announces that her ninth album, Evermore, will be out on December 12. This is the death knell for fans still holding out hope that, somehow, the Lover campaign might have picked back up post-pandemic with “Cruel Summer” as a single.

February 11, 2021: Swift announces Fearless (Taylor’s Version), the first of her six planned rerecorded albums. This marks Swift’s third album cycle since the Lover era was cut short, with all signs pointing to the idea that fans are just a few years away from Swift tweeting “i don’t remember LOVER.”

February 26, 2021: Swift officially cancels Lover Fest for good, citing the “unprecedented pandemic.”

April 1, 2021: Rodrigo releases “deja vu,” the second single from her debut album, Sour. A few days later, she says the song’s bridge is directly inspired by the bridge in “Cruel Summer”: “It’s one of my favorite songs ever — I love, like, the yell-y vocals in it,” she tells Rolling Stone. “I wanted to do something like that.”

April 2, 2021: Clark reveals a shred more information about how “Cruel Summer” was written: “Gosh, it was really casual,” she tells NME. “Just some people in a room jammin’.”

May 20, 2021: Clark reveals that, sometime around 2015, Swift invited her over for a cooking lesson. “I don’t exactly remember why,” she tells Jessie Ware on the Table Manners podcast. “I don’t remember if she experienced that I couldn’t cook and thought: ‘I’m going to help this girl.’” Clark later tried to re-create the recipe Swift taught her, only to end up serving her guests steaks that were like “hockey pucks.”

July 9, 2021: Swift, Antonoff and Clark are retroactively given writing credits for Rodrigo’s “deja vu,” amounting to about 50 percent of the publishing royalties, because of the song’s “Cruel Summer” reference. The crediting makes numerous headlines and sparks widespread debate over the practice (and likely alerts many casual fans to “Cruel Summer”’s existence.)

August 31, 2021: Another cruel summer passes. This one was probably cruelest for Rodrigo; Billboard later estimates that the young singer-songwriter has given up “millions” in royalties because of her splits with Swift, Antonoff, and Clark, as well as with Paramore for “good 4 u.”

December 9, 2021: In an interview with Time, Rodrigo says it was “frustrating” to have people “discredit and deny my creativity” by suggesting she cribbed elements of “deja vu” and “good 4 u” from other songs. Her producer, Dan Nigro, says “people get funny about things when songs become really popular.”

June 17, 2022: The Summer I Turned Pretty, an adaptation of the popular YA books by Jenny Han, is released on Prime Video. “Cruel Summer” is featured in one of the episodes, leading to a resurgence in the song’s popularity.

August 28, 2022: Swift announces that Midnights, her tenth album, will be released on October 21.

August 31, 2022: The end of another cruel “Cruel Summer”–less summer.

November 1, 2022: Swift announces her massive, career-spanning Eras tour — the first time any songs from Lover will be performed live.

March 17, 2023: The Eras tour begins in Glendale, Arizona. “Cruel Summer” is the second song on the set list. Swift’s performance of the track seems to acknowledge the way that the song’s bridge has become one of the most beloved in her oeuvre. Each night on tour, she introduces the bridge with some variation on the following: “We have reached the very first bridge of the evening, ladies and gentlemen — I would prefer that we cross it together, and by cross it, I mean scream it.” This portion of the show instantly becomes one of the Eras tour’s many viral TikTok moments, with fans filming and posting it from every possible angle as the tour rolls on.

March 23, 2023: “Cruel Summer” reenters the global Spotify charts, three and a bit years after its initial release, at No. 147, and the U.S. Spotify charts at No. 69, a resurgence likely spurred on by both the widespread coverage of the tour and its huge presence on TikTok.

April 9, 2023: Swift and Alwyn break up after six years. Some fans think they’re beginning to notice a dissociated glaze come over Swift’s eyes when she performs some songs about their relationship, but “Cruel Summer” remains an elated highlight.

June 3, 2023: “Cruel Summer” reenters the Billboard Hot 100 at No. 49. On the U.S. Spotify chart, it’s sitting at No. 16.

June 15, 2023: Seeking to capitalize on the resurgence of the track — and, likely, preemptively stop rabid fans from doxing its radio promotion team — Republic Records announces that “Cruel Summer” will be sent to U.S. pop radio. (Fans on Reddit are, understandably, not okay upon hearing this news: “YOU’RE WELCOME FOR THE 500 STREAMS A DAY”.) For those keeping track, this is the third project that Swift is actively promoting at this point in time, after Midnights and Speak Now (Taylor’s Version).

June 17, 2023: At a show in Pittsburgh, Swift tells the audience that the resurgence of “Cruel Summer” is “the weirdest, most magical thing,” and that she always intended for it to be a Lover single. “‘Cruel Summer,’ that song was my pride and joy on [Lover],” she told the audience. “I’m not trying to blame the global pandemic that we had, but that is something that stopped ‘Cruel Summer’ from ever being a single.”

July 6, 2023: Justin Trudeau tweets at Swift, saying it’ll be “another cruel summer” if she doesn’t play shows in Canada. Hope she sees this, bro!

July 10, 2023: “Cruel Summer” enters the top ten of the Billboard Hot 100 at No. 7, nearly four years after its initial release. It’s Swift’s 41st career top ten.

August 14, 2023: “Cruel Summer” peaks at No. 3 on the Hot 100, held off by two country songs — Morgan Wallen’s “Last Night” and Luke Combs’s cover of “Fast Car.” Chart-obsessed fans are confident that “Cruel Summer” will finally hit No. 1 a week later.

August 21, 2023: Except that it doesn’t — “Cruel Summer” slips back down to No. 4 on the Hot 100, pushed aside by yet another country song: Oliver Anthony Music’s right-wing dog whistle “Rich Men North of Richmond.”