Taylor Swift has had lots of collaborators over the years, from country songwriter Liz Rose to legendary pop producers Max Martin and Shellback, but it’s Jack Antonoff that has arguably left the biggest handprint on her discography.
Swift and Antonoff first teamed up in 2013 for “Sweeter Than Fiction,” which they cowrote for the film One Chance. They then collaborated on three songs from Swift’s 2014 album 1989: “Out of the Woods,” I Wish You Would,” and the bonus track “You Are In Love,” which was inspired by Antonoff and his then-girlfriend, Lena Dunham.
The pair developed a close friendship in addition to their professional compatibility. Antonoff has contributed to all of Swift’s albums since 1989, helping to shape her signature pop sound. After Folklore won Album of the Year at the 2021 Grammys, Antonoff penned a heartfelt Instagram tribute to Swift.
“You are the one who let me produce records first,” he wrote. “Before you I just ‘wasn’t a producer’ according to the herbs. I just wasn’t let in that room. then I met you, we made out of the woods and you said, ‘that’s the version’ and that changed my life right there.”
Swift has also gushed about Antonoff, who went on to produce for artists including Lorde, St. Vincent and Lana Del Rey.
“[Jack’s] excitement and exuberance about writing songs is contagious,” she told The New York Times in 2017. “He’s an absolute joy. That’s why everyone loves him. I personally wouldn’t trust someone who didn’t.”
Now that Swift’s first album to feature Antonoff is officially a decade old, Us decided to do the impossible: rank the iconic duo’s top 13 collabs.
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13. ‘Lover’
The song that defined the album and era of the same name, “Lover” harkened back to a time before 1989 when Swift’s instrumentation relied heavily on piano and guitars. With lyrically specific verses and an anthemic chorus, Swift proved yet again with “Lover” that no one writes about matters of the heart better than her. Antonoff coproduced the song, but Swift was the sole songwriter.
12. ‘Ivy’
One of Swift’s most underrated songs, this Evermore track feels like coming “in from the snow” to a warm cottage with tea warming on the stove. Fingerpicked guitar and banjo lines serve as the beautiful backdrop to a tale of star-crossed lovers with a seriously satisfying bridge.
The National’s Aaron Dessner, another frequent collaborator of Swift’s, also worked on “Ivy,” so it doesn’t have as much of Antonoff’s signature sound as other songs on this list.
11. ‘Anti-Hero’
“Anti-Hero” is the lead single off Midnights, which Swift has described as her “first album [Jack and I have] done with just the two of us as main collaborators.” The song’s instrumentation is familiar territory for Swift and Antonoff — a drum loop and retro synths — but the overall sound is a more mature version of the work Swift and Antonoff began together on 1989.
Antonoff, who cowrote and coproduced the tune, told Time in 2023 that “Anti-Hero” was “mostly built” around “a really weird synthesizer that has a different attitude every time you turn it on” and a Linn Drum beat.
“These are all things I didn’t even have when I was producing ‘Out of the Woods,’” he said.
10. ‘This Is Me Trying’
Folklore was Swift’s first time collaborating with Dessner, but Antonoff’s contributions to the album are some of its strongest moments; “This Is Me Trying” is one of those standouts. The hypnotic track, which features organs and horns, allows the poignant lyrics to shine.
“Pulled my car off the road to the lookout, could’ve followed my fears all the way down,” Swift sings on the first verse.
A highly relatable account of hitting rock bottom, “This Is Me Trying” is the perfect song to show anyone who claims that Swift only writes bubblegum pop or songs about her exes.
Antonoff cowrote and coproduced the tune. (Swift’s then-boyfriend Joe Alwyn is also listed as a coproducer.) And maybe it’s just because “This Is Me Trying” is in Swift’s lower register, but Us could hear it in Antonoff’s voice before he performed it at the Ally Coalition’s 7th Annual Talent Show in December 2020.
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9. ‘Gold Rush’
“Gold Rush,” a song about an infuriatingly good looking person, is a more sophisticated version of Reputation’s “Gorgeous.” The only Evermore tune that Swift and Antonoff cowrote and coproduced alone, it’s one of the best songs on the album, and it should’ve been a hit.
Despite the track’s ample instrumentation, which includes strings, horns and an organ, Swift’s lush vocals take center stage along with her clever lyricism.
8. ‘Guilty as Sin’
Some of Antonoff and Swift’s critics have complained that all the duo’s collaborations sound the same, but they charted new territory with this sensual soft rock song. “Guilty as Sin” is catchier than many of the more conventional pop songs on The Tortured Poets Department with lush vocal harmonies and a sweeping and melismatic chorus.
7. ‘Getaway Car’
Of all Antonoff and Swift’s creations, “Getaway Car” arguably sounds the most like a Bleachers song. But despite Antonoff’s clear influence, the Reputation tune is still undeniably Swiftian, with lyrically dense verses and a damn good metaphor on the chorus: a getaway car as an ill-fated rebound.
Even those with merely a peripheral understanding of Antonoff and Swift’s partnership will recognize “Getaway Car” as their musical lovechild. It’s epic, reminiscent of ‘80s pop and seriously catchy.
6. ‘You’re on Your Own, Kid’
Us named this Midnights song Swift’s second-best track five of all time for its satisfying lyrical turn, when the title transforms from an unfortunate fact of life to a comforting maxim. “You’re on Your Own, Kid” is one of Swift’s most personal and confessional songs, but it’s still relatable to anyone who’s ever felt like they can only count on themselves.
The muted guitars and relatively sparse instrumentation make “YOYOK” feel as intimate as the lyrics. Swift kicks the soft and dreamy vocal into high-gear during the emotionally climactic final chorus when she sings, “I looked around in a blood-soaked gown and I saw something they can’t take away / Cause there were pages turned with the bridges burned, everything you lose is a step you take.”
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5. ‘All Too Well (10 Minute Version) (Taylor’s Version) (From the Vault)’
Before anyone comes at Us for this masterpiece’s ranking, consider the fact that Antonoff didn’t contribute to the original song from 2012’s Red, which was cowritten by Swift and Rose and coproduced by Swift and Nathan Chapman. However, credit must be given for the care that Antonoff took when coproducing the highly-anticipated 10-minute version, released on Red (Taylor’s Version) in 2021.
Instead of recreating the sound of the original “All Too Well” — the approach that Swift and producer Christopher Rowe more or less took for “All Too Well (Taylor’s Version)” — Antonoff and Swift did something new for the 10-minute rendition. The production is dreamier and less polished, complementing the raw emotion of the additional lyrics.
4. ‘Mirrorball’
“Mirrorball” is one of Swift’s best-sounding songs to date. Between the shimmery tambourine, warm guitars and prominent ethereal vocals, the Folklore tune sounds so pretty that it’s easy to miss how striking the lyrics are on the first listen. Written and recorded during the early days of the COVID-19 pandemic, the song explores Swift’s struggle to remain relevant despite the fickle nature of fame.
“When they sent home the horse and the rodeo clowns, I’m still on that tightrope / I’m still trying everything to get you laughing at me,” she sings.
3. ‘Out of the Woods’
Antonoff was still finding his sound as a producer when he and Swift teamed up for this 1989 track. His style was bold and brash, which is why this song remains so iconic. Featuring heavy synths, a punchy drum loop and a choppy vocal hook sung by Antonoff, “Out of the Woods” was one of the defining songs of 1989, an album that changed the trajectory of Swift’s career by confirming her pop star status.
Swift also collaborated with tried and true pop producers Martin and Shellback on 1989, but her decision to work with then-unseasoned Antonoff on “Out of the Woods” and “I Wish You Would” proved that she was following her own artistic instincts. That risk would help shape Swift’s sound for years to come.
2. ‘Cruel Summer’
“Cruel Summer,” which Swift and Antonoff cowrote with St. Vincent, is pop perfection. It’s strange to refer to any of Swift’s songs as a sleeper hit, but this Lover track might’ve earned that title by topping the Billboard Hot 100 for the first time in October 2023, more than four years after its initial release. The chorus is arguably Swift and Antonoff’s catchiest, and the cathartic bridge, which starts with “I’m drunk in the back of the car,” is so good that it comes back again after the final chorus.
1. ‘August’
It’s hard to find a Swift song with production that better complements and serves the songwriting than Folklore’s “August.” Soaring strings and dense reverb match the wistful longing of the narrator, who misses a “moment in time” and the person they shared it with — despite knowing “you were never mine.”
Swift has revealed that she thinks of “August” as part of a trilogy of songs about a love triangle — “Cardigan” and “Betty” complete the trio — but the song stands on its own as one of Swift and Antonoff’s most evocative pieces.
“Back when we were still changing for the better, wanting was enough / For me it was enough, to live for the hope of it all,” Swift sings on the bridge, which feels like the bittersweet climax of a coming-of-age film.
