In a new Esquire cover story, “Jake Gyllenhaal Reconsiders” or, in print format, “Jake Gyllenhaal Is Not the Man You Think He Is,” the eponymous actor appears for one of those “reportage”-type articles that few magazines really have the budget to employ writers for anymore. But this is still Esquire, even if not heyday Esquire, and when a senior editor like Eric Sullivan is writing the piece, the “budget” magically appears. Not that much money is required for the outing described in the article itself, wherein Sullivan accompanies Gyllenhaal on a car ride upstate (the place Sullivan himself grew up in) so that the latter can take him to a racetrack and show off something like “effortless masculinity.” What’s more, Gyllenhaal provided the snacks in the form of an energy bar and some nuts and offered to drive the “beat-up Jeep” that belonged to Sullivan. But hopefully, he didn’t offer to pay for the gas as well. For even that is becoming expensive-seeming to the celebrity bank account.
These are all seemingly “insignificant” details that sound ripe for the making of a Taylor Swift song like “All Too Well.” The fan favorite from 2012’s Red that got a major refresh for the re-release of her fourth album. Indeed, the now ten-minute track (for Taylor wanted to give the fans the original incarnation they had long craved) is also a “short film” (a.k.a. “Ride”-length music video), too. One that is both aggressively white and herteronormative and also very heavily resembles a particular initial date Swift shared with Gyllenhaal at the outset of their relationship. That’s right, a trip upstate. Complete with a leading man—Dylan O’Brien—that looks very similar to Jake, as well as a leading lady—Sadie Sink—who, although she might not have Swift’s signature blonde locks, is deliberately around the same age as Swift would have been at the time of the relationship and subsequent breakup in question. Same as O’Brien being twenty-nine at the time of the project’s genesis—Jake’s age in 2010 (before turning thirty in December; a milestone Swift did not get to celebrate with him, just as Gyllenhaal chose not to show up to her twenty-first birthday that same month).
As Sullivan takes his time getting to the all-important question of how Gyllenhaal felt about Swift’s re-release and the subsequent “reboot” of her fans’ contempt for him, it bears noting that Swift is that rare breed of a modern artist—particularly a female one—who openly admits to using her songs as “documents” (a.k.a. revenge pieces) of what really happened between her and an erstwhile lover (something that Olivia Rodrigo has also modeled her own songwriting style after). Thus, her candid statement circa 2012, “The only way that I can feel better about myself—pull myself out of that awful pain of losing someone—is writing songs about it to get some sort of clarity.” Even the video for “All Too Well” itself is a big indication of how much Swift, unapologetically so, seeks to exact some form of vengeance, er, “clarity” on the boy who did her wrong when a relationship draws to its perhaps unavoidable end (though many are aware that Swift likely wouldn’t stand for an end with Joe Alwyn).
Unlike Sullivan, maybe Taylor wasn’t taken to the Monticello Motor Club (members only, naturellement) in the Catskills, but she was taken to Hopewell Junction for some apple picking back in 2010—a fall-oriented jaunt that gets loosely re-created in the music video. And, if fans know Taylor like they think they do, there can be no mistaking the fact that she repurposed the word “well” next to “hope” into something far more knowingly jaded: “All Too Well.” Although the honeymoon period was as long as the relationship itself—just three months—Swift, like Mariah writing “My All” and “The Roof” about a nominal encounter with Derek Jeter, seemed to want to turn molehills into mountains with regard to immortalizing the dalliance as an epic (and accusatory) track. And that she has, twice over.
As for Gyllenhaal, maybe Swift has met her match in the game of undercutting shade as Sullivan mentions in his article, “Gyllenhaal doesn’t like to sing; he loves to sing. He’s loved to sing since he first watched the biopic La Bamba. As a boy, he’d sing its title song over and over as he strummed a tennis racket, doing his best Ritchie Valens by way of Lou Diamond Phillips.” The following quote from his sister, Maggie (the one supposedly still holding that red scarf hostage), corroborates, “He was so into that movie.” Sullivan adds, “At his production company’s holiday party… he leads attendees in a Christmas carol sing-along. He knows, just knows, it makes everyone feel better, even those who at first decline.” Gyllenhaal’s love of song, one would think, might have been tainted by how Swift tends to use the artistic medium for “catharsis,” but not so, the article indicates. For he still insists, “Even if people sing just a tiny bit, it makes me feel good. When you’re singing, there’s no shot other than opening up. It has to be heart first.” Which would tend to mean Swift’s heart is filled with rage. In any case, his sister confirmed that when Jake sings (as he did for Sunday in the Park with George), “It’s almost like this clear channel expressing who he is. There’s nothing blocking it.” Gyllenhaal’s love of singing translates naturally to karaoke and, “At one point, when [Sullivan] asks if he’s ready for more questions, he says, ‘Sure. I mean, we could do that. Or we could just sing karaoke.’” One would guess that “We Are Never Ever Getting Back Together,” even if highly appropriate, might not make the list for his self-expression.
Besides, Gyllenhaal has a new love in his life. And the article not only mentions that the two have been together for three and a half years (much longer than three months), but also expressly highlights French model Jeanne Cadieu’s age: “Gyllenhaal and Cadieu, twenty-five, spent the first months of lockdown in the Los Angeles guesthouse of his godmother, Jamie Lee Curtis.” Apart from iterating the fact that Gyllenhaal has always been surrounded by Hollywood royalty (sort of like Eve Babitz), it also seeks to vindicate Taylor’s lyric about his lovers never getting older (“I’ll get older, but your lovers stay my age”). You know, because he’s a classic pedo type who “gets bitches” in their twenties (all in the style of the sort of man described in Taylor’s “The Man”). To further call out Gyllenhaal’s hypocritical tendencies, a line about him having a keychain that reads, “Fuck the patriarchy” was added in the new “All Too Well,” complete with the visual of O’Brien having one as well in the video. But men who say “fuck the patriarchy” and mean it probably wouldn’t pursue such age-inappropriate women. In fact, only women should pursue age-inappropriate men if the patriarchy is to be truly dismantled (#thankyouMadonna).
Despite Gyllenhaal declaring his happiness with the present, Sullivan probes about how “affected” Jake must have been by the Swiftie fan hate in the aftermath of “All Too Well” (Taylor’s Version) to actually turn his comments off on social media. Jake decided to reply, “It has nothing to do with me. It’s about her relationship with her fans. It is her expression. Artists tap into personal experiences for inspiration, and I don’t begrudge anyone that.” Said like someone who knows goddamn well it has everything to do with him and who is therefore holding a grudge. For how could you not when you know your infinitely more famous ex has objectively “won” at the game of holding you accountable for your actions?
Regardless, Gyllenhaal took it as an opportunity to philosophize, “At some point, I think it’s important when supporters get unruly that we feel a responsibility to have them be civil and not allow for cyberbullying in one’s name… Not about any individual, per se [*cough cough* Taylor, is what he means to specify], but a conversation that allows us to examine how we can—or should, even—take responsibility for what we put into the world, our contributions into the world. How do we provoke a conversation?” In other words, it sounds like he’s essentially saying that people, and women in particular, shouldn’t express their heartbreak in songwriting so as to spare fragile men the potential consequence of being harassed by fandoms. Yet where was this philosophy when Britney Spears was being smeared by the media in a pre-socials world after Justin Timberlake released “Cry Me A River”?
Jake continues, “There’s anger and divisiveness, and it’s literally life-threatening in the extreme.” Of course, Gyllenhaal himself knows better than to expect anything like a death threat from a Swiftie, which is why Sullivan adds into the paragraph, “I ask if his life has been threatened recently; he says no, that’s not what he’s suggesting.” Here Gyllenhaal takes it to his faux philosophical extreme with, “My question is: Is this our future? Is anger and divisiveness our future?” Well, first off, it’s our present, and secondly, yes, unquestionably it’s the future, to boot. But Gyllenhaal sees Swift’s art as a source of divisiveness (as all great art usually has been) turning people against him as an opportunity to posit, “Or can we be empowered and empower others while simultaneously putting empathy and civility into the dominant conversation? That’s the discussion we should be having.” Sullivan then writes of the conversation topic wrapping up, “He shrugs, his hands raised in the air as if to convey, What more is there to say? Has he listened to the album? ‘No.’” It all comes across as elaborate doublespeak designed to “subtly” flip the script on Swift as the villainous figure in this scenario. When, in fact, she’s merely, as he phrased it, “tapping into her personal experience for inspiration.” Of course, the shade here is that Gyllenhaal did not experience it the way she did. From the perspective of a “petulant little girl,” in his eyes.
In the final lines of the article, Sullivan describes, “He turns to me. ‘Shall we sing a song?’ he asks—earnestly, I think—his eyes glinting in the fading light of the winter afternoon.” One would like to imagine the song is “All Too Well,” but, in reality, it was probably something by Sean Paul. For, as Gyllenhaal very clearly declared, he doesn’t fuck with Red—not either version. Yet, the truth is, it doesn’t matter if the ex that spurred the artistic work in question never “absorbs” it. Even if they did, they would never see it from your perspective anyway. What matters, ultimately, is that it resonates with other people who find meaning in it, identify with the same pain. Which, obviously, Swift has never had trouble achieving in her work.
