Hi, Swifties. We don’t tend to have a lot in the way of Taylor Swift coverage around these parts, but assuming you found your way here during your fervent search for details on whether Taylor Swift is involved in Toy Story 5 after her team seemingly jumped the gun by posting and quickly removing a countdown suggesting it: welcome!
Swift caused a stir in her own community and the film world at large with the update, causing speculation as to whether she may be lending her voice to the upcoming sequel, or perhaps contributing a song to it. Any time Taylor decides to dip into movies in any capacity, there’s a ton of buzz. Comes with being one of the voices of our generation, I suppose. So what exactly does Swift’s tease mean for Toy Story 5? Given what’s already been announced about the plot of the movie, I feel like I’ve got a pretty solid hunch.
First, is Swift going to be voice-acting or contributing a song to the movie? It could be possible that Swift’s voicing a new character, maybe even something as minor as a cameo… but would that really necessitate a big, splashy countdown on her website? No, something that high-profile seems better suited to the announcement of new music to which her legions of adoring fans can either jam out or sob… and I’m willing to bet a new-in-box Sheriff Woody it’s going to be tonally closer to the latter.
Why am I so sure there’s a tear-jerking Toy Story/Taylor Swift tune coming? That’s all got to do with what we already know about Toy Story 5’s story. Though Toy Story 5 has, broadly speaking, been marketed as a treatise on “toys vs. electronics,” Buzz Lightyear voice actor Tim Allen said last year that the movie is “a lot about Jessie.” Are you starting to see where this is going?
I’ll give you a hint: emotionally? It’s under a bed. Abandoned and forgotten.
Why am I so sure there’s a tear-jerking Toy Story/Taylor Swift tune coming? That’s all got to do with what we already know about Toy Story 5. “
Jessie, Woody’s stalwart deputy voiced by the incomparable Joan Cusack, has long deserved some time in the spotlight after first debuting in 1999’s Toy Story 2. Her plucky, eternal optimism contrasted with Woody’s neurotic nature alone made her an instant favorite, but it was what we learned about how she came into the possession of unsavory toy collector Al McWhiggin that earned her a permanent place in Pixar fans’ hearts and sympathies.
Jessie recounts the story to Woody of her previous life as the favorite toy of a young girl named Emily. Jessie loved nothing more than being this child’s plaything, gallivanting around during the day on adventure after adventure and falling asleep together every night. But as kids do, Emily started growing up and began to neglect Jessie to the point of leaving her under the bed to collect dust until, one day, she dropped Jessie off on the side of the road for donation to charity. It’s unquestionably one of the most devastating sequences ever rendered by Pixar, and went a long way to cementing Jessie as a top-shelf Toy Story character… and the whole scene is scored by the hauntingly beautiful “When She Loved Me” by Sarah McLachlan, one of the most celebrated singer-songwriters working at the time of Toy Story 2’s release. “Building a Mystery,” “Adia,” “Angel,” “I Will Remember You,” “Sweet Surrender”… I could go on. The lady’s a Canadian national treasure and she still sounds incredible.
With Toy Story 5 confirmed by Tim Allen to be “a lot about Jessie,” and the most recently released trailer highlighting Jessie’s anxiety at the idea of being replaced again, this time by Bonnie’s new tablet Lilypad (voiced by Tron: Ares’ Greta Lee), it’s easy to imagine there being room for a moment to echo Jessie’s McLachlan-scored abandonment (and indeed, the original Woody vs. Buzz dynamic from the first Toy Story) with a powerhouse modern analog to McLachlan… and you can’t really do better than Taylor Swift in that arena. Toy Story 4 went out of its way to give Woody closure by reuniting him with Bo Peep, not seen since Toy Story 2, so it’s easy to imagine Pixar wanting to afford the same catharsis to his deputy here.
Taylor Swift would’ve been about 10 years old (right around Emily’s age) when Toy Story 2 came out, so I can only imagine how impactful that scene must have been for her… maybe enough to follow in Sarah McLachlan’s footsteps by contributing a song of her own to a pivotal turn in Jessie’s story. Although, there’s a shot in the most recently released trailer that seems to be a recreation of that Toy Story 2 flashback, so a Taylor Swift cover of “When She Loved Me” doesn’t seem out of the question either.
Is this a new version of an old flashback, or history repeating itself with Bonnie?
There’s even an extra layer of nostalgia to consider here: As Swifties were quick to point, out once the countdown was erroneously posted on her site, Toy Story 5’s June 19 release date also happens to mark the 20th anniversary of her very first single, “Tim McGraw.”
In any case, there’s a new Toy Story on the horizon, and you know what that means: Reach for the sky. And the tissues.
Toy Story 5 is in theaters June 19, 2026.
