Jessie’s Girl?

I’m Convinced Taylor Swift Wrote A Song For The Best Toy Story Character

Is it too soon to predict an Oscar nom?

by Grace Wehniainen
HOLLYWOOD, CALIFORNIA - MARCH 26: Taylor Swift attends the 2026 iHeartRadio Music Awards at Dolby Th...
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Taylor Swift always has something cooking (and not just sourdough bread).

On April 30, fans noticed that the musician’s official website displayed a countdown with a strikingly familiar background resembling the clouds from Andy’s bedroom wallpaper in the Toy Story films. The numbers of the countdown were also yellow with a blue outline, not unlike the franchise’s logo.

As of writing, the mysterious countdown no longer appears — you can still check it out for yourself through the Internet Archive — but that’s only fueled further speculation. Plus, fans noticed that days earlier, Swift stepped out in New York wearing a light blue dress, red shoes, and a yellow purse: a color-maxxing moment that, in hindsight, feels very Toy Story-ian. So, is Taylor Swift writing a song for the Toy Story 5 soundtrack?

It certainly seems like she might be! Specifically, as several Swifties have pointed out, it would make extra sense for the musician to pen a song about Jessie, Woody’s fellow Western doll who debuted in Toy Story 2.

Given Swift’s country roots, how fitting would it be to write a song about a cowgirl like her? Such a track could play a pivotal role in the upcoming film (in theaters June 19) because, as Entertainment Weekly notes in their preview, Jessie takes center stage this time around, embarking on quite the journey as she reckons with a world that increasingly favors electronics (like the movie’s fictional Lilypad tablet) over traditional toys.

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As Joan Cusack (who voices the kind, independent cowgirl) told the outlet, “I know every parent in the United States worries about their kids. When do you get them involved in tech? What does that do to their brains? And that’s what this movie’s about. It’s about humanity and playing and loyalty — and it makes me cry.”

Speaking of tears, go ahead and rewatch the Toy Story 2 scene where Jessie reflects on being left behind by her kid, Emily. The devastating montage is set to Sarah McLachlan’s achingly beautiful “When She Loved Me,” which was written by Randy Newman and nominated for an Oscar. For Swifties manifesting an EGOT for the musician — who already has one Emmy and a slew of Grammys — writing a Jessie-centric song for the beloved franchise could certainly be a plausible move toward that coveted award.

Even beyond the cowgirl ties, you can be confident that the musician who wrote “Nothing New” and “Clara Bow” would have something to say about a character with that specific pang of feeling like the world’s outgrown her.