Throughout her career, Taylor Swift has landed 232 songs on the Billboard Hot 100. Included in that are the 49 songs that broke into the Top 10. Within that, 11 topped the chart. Despite having an inescapable presence in pop for over a decade, there’s one artist’s record in particular that sparked envy in her. “‘Better Now’ is so insane,” she told Post Malone when she passed him backstage at the 2018 Billboard Music Awards. “I’m so jealous of that song — that hook.” Last year, in an interview with Howard Stern, Malone recalled the interaction, saying: “I was like what? That’s fucking crazy, you’re a great fucking songwriter, thank you so very much.”
That initial moment of Swift and Malone’s paths crossing didn’t necessarily feel foundational at the time. They still largely existed within different spheres of pop music. But as Swift started chipping away at her re-recording process, Malone became a probable contender when fans speculated about potential bonus track collaborators for Reputation (Taylor’s Version), given the hip-hop influences present on the original release. Instead, their collaboration actualized on The Tortured Poets Department, the eleventh studio album from Swift on which Malone appears on “Fortnight,” its opening track and first single. “She hit me up and said, ‘Let’s do it.’ And I was like, hell yeah,” Malone recently told Apple Music’s Zane Lowe.
“Fortnight” being the very first song on the album puts it in a prime position for charting success — curious Malone fans who aren’t tapped into Swift’s universe might only listen to their collaboration, and Swifties who have been theorizing about all the potential narratives that The Tortured Poets Department could span would never dare listen on shuffle. Plus, there’s a music video on the way.
Malone’s own chart history boasts 76 entries on the Hot 100, including 11 that landed in the Top 10 hits and four that reached the top spot. It was on the career-defining, blockbuster records Beerbongs & Bentleys (2018) and Hollywood’s Bleeding (2019) that he proved himself to be a true hitmaker — the kind of superstar who, like Swift, can dispense Top 40 tracks like he was churning them out of a gumball machine.
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Beerbongs & Bentleys, in particular, was a significant turning point, producing two chart-topping singles with “Rockstar” and “Psycho,” his collaborations with 21 Savage and Ty Dolla $ign, respectively. But “Better Now” proved to be the most pivotal cut. The record charts the dissolution of a relationship that Malone can’t seem to escape the ghosts of, perpetually haunted by his own mistakes and reminders of the future he envisioned but will never have. The song spent 52 weeks on the Billboard Hot 100, surpassing both collaborative singles despite peaking at No. 3 — during which time it lodged itself into Swift’s listening rotation.
The remorseful “Better Now” chorus that Swift was so enthralled by — “You know I never meant to let you down, let you down / Would’ve gave you anything, would’ve gave you everything” — strikes the same chord of regret and dismantled relationships that she played across Reputation, the album she released in 2017 following a major shift in her public perception. “Should’ve known I’d be the first to leave,” she sang on the “Getaway Car,” spending far less time glancing in the rearview than Malone. “Think about the place where you first met me.”
That album deep-cut was one of the few produced by Jack Antonoff, who has since become Swift’s primary collaborator. “Fortnight” features writing credits from Swift and Malone, as well as Antonoff, who presumably produced it as well. When the record was announced in February — just after the 2024 Grammy Awards and before the Super Bowl — Malone suggested that he hadn’t heard the final recording yet. The announcement of their collaboration sparked curiosity about whether his own right-hand collaborator, Louis Bell, made it into the room for “Fortnight.”
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Bell shares six Diamond-certified singles with Malone, including “Better Now.” He also — in the wake of her admiration — teamed up with Swift during the recording sessions for the Reputation follow-up Lover, which arrived in 2019. Bell co-wrote and co-produced the album’s opening track, “I Forgot That You Existed,” and the deep cuts “Afterglow” and “It’s Nice to Have a Friend.” Last year, Swift surprise released another collaboration that emerged from the session, the synth-pop track “All of the Girls You Loved Before.” Bell was working with Malone on Hollywood’s Bleeding around the same time that Lover was being crafted, and the albums were released two weeks apart.
Speaking to Howard Stern about Swift’s acknowledgment of his single, Malone added: “There are so many beautiful artists in the world, and for another artist to acknowledge that … it’s a really special thing. That was a really cool moment, and it was very inspiring.” There was a certain grit to his pop performance on “Better Now” that blurred genre lines in a more intentional way than the pure pop pivot that he made on “Circles” the following year. And while there might not be significant overlap in their sonic approaches, Swift and Malone have spent time on their creative projects interrogating their positioning in the ring of public spectacle.
In the aftermath of Beerbongs & Bentleys and Hollywood’s Bleeding, Malone made a conscious effort to recenter himself creatively with Twelve Carat Toothache (2022), his fourth studio album, which opens with the fame-confronting song, “Reputation.” Flipping the traditional pop format and placing a chorus where an opening verse should be, he sang: “I got a reputation that I can’t deny / You’re the superstar, entertain us.” The songs on that album, Malone told Billboard in 2022, “speak more to how I’m feeling at the moment: the ups and downs and the disarray and the bipolar aspect of being an artist in the mainstream. I’ve made a lot of compromises, especially musically, but now I don’t feel like I want to anymore. I don’t need a No. 1; that doesn’t matter to me no more, and at a point, it did.”
Swift framed her own eminence in varying ways across Reputation. There was the line “My reputation’s never been worse, so you must like me for me” on “Delicate” and a barrage of references on “End Game.” But Swift’s most striking round in the ring — where she wrestled with the bizarre relationship between artistry and celebrity — arrived not through a song but through a poem. “Why She Disappeared,” which was printed in magazines created for the Reputation era, was colored with paranoia and pleading for understanding, putting weapons in the hands of phone calls, promises, and the past. Once those are all put to use, and there’s nothing left standing, she wrote: “And in the death of her reputation, she truly felt alive.”
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Stripping the power from external influences opened the door for an exploration of new musical realms for Malone, even if none of its singles cracked the Hot 100’s coveted Top 10. Last month, the singer appeared as a featured artist on “Levii’s Jeans” from Beyoncé’s country-sculpting Cowboy Carter. And Malone is expected to make an anticipated country pivot himself. Swift, on the other hand, is somehow only becoming more famous, a fact that makes her labyrinthine relationship with public perception — and in turn, validation — both complicated and intriguing.
The Tortured Poets Department will keep her positioned in the glow of a blinding spotlight — and “Fortnight” will illuminate Malone, too. “I’ve been such a huge fan of Post because of the writer he is, his musical experimentation and those melodies he creates that just stick in your head forever,” Swift wrote on social media a few hours before the album’s release. “I got to witness that magic come to life firsthand when we worked together on Fortnight. Honestly can’t wait for you guys to hear this song.”
