In Toy Story 5, the battle isn't just between toys and technology—it's a deeply personal journey for Jessie, the yodeling cowgirl who steps up as sheriff. The film's co-director Kenna Harris and producer Lindsey Collins recently sat down with Collider to break down how the fifth installment came together, including the surprising late-stage discovery of Jessie's connection to her past and the dream collaboration with Taylor Swift.
Set when Bonnie struggles to make friends, her parents buy her a tablet named Lilypad (voiced by Greta Lee). This new device immediately clashes with Bonnie's toys, especially Jessie (Joan Cusack), who takes it upon herself to help her kid find a real friend. Along the way, Jessie reconnects with her own history in a poignant twist that reshapes the entire story.
Jessie Takes the Lead from the Start
According to Harris, the decision to center the film on Jessie came right at the beginning. "Andrew Stanton wrote on Toy Story 4 and all the previous films. It was one of his big decisions to really just push for Woody to give away the sheriff badge to Jessie," she explained. "So when Pixar was sniffing around like, 'Is it time for Toy Story 5? Andrew, what would you do with it?' His instinct right away was, 'Well, Jessie is the head of the room. It's got to be a story about her.'"
That instinct resonated with the entire team. "There's so much exciting emotional territory to explore with her," Harris added. "So right from the get-go, there was always Jessie as the lead, Lilypad as our antagonist, and 50 Buzz Lightyears just going rogue." Collins laughed, noting that the 50 Buzz Lightyears idea was pure Stanton: "Two feel obvious. The third one, I don't know, and Andrew was like, 'Just wait for it, it's going to work.'"
The Emily Connection Came Late—But It Was Worth the Wait
One of the film's most emotional beats involves Jessie reconnecting with Emily, the girl who owned her before Woody. Harris admitted that this reveal wasn't locked in early. "It transformed over time," she said. "There were different kinds of ways we were trying to explore what exactly is the hurt that she has. What exactly would help that?"
Collins confirmed it came "pretty late in the game." Harris added, "We knew right away that this feels right, and this feels like what she deserves." The result is a deeply satisfying arc that honors Jessie's history while moving her forward.
Taylor Swift's 'I Knew It, I Knew You' Was a Patient Gamble
Perhaps the most buzzed-about element of Toy Story 5 is Taylor Swift's original song, "I Knew It, I Knew You," which plays over the film's emotional finale. According to Collins, Swift was always the dream choice. "Taylor was, and then we were like, 'There's no way. She's so busy,'" Collins recalled. "You know that little tour called The Eras Tour?"
Rather than settling for a backup, the team decided to wait. "We left it really... we had talked about it. And it was like, 'Too busy. It's not going to happen.' And then it was like, 'Alright, what if we just wait and just hold and see?'" Collins said. "Let's just see how the movie evolves and not commit to anything else."
That patience paid off. "Then the universe delivered in the sense that all of a sudden it was like, 'Wait, she might have a minute,'" Collins added. The result is a song that perfectly caps Jessie's journey—and proves that sometimes the best things come to those who wait.
Toy Story 5 is now in theaters, featuring the voices of Tom Hanks, Tim Allen, Joan Cusack, and Conan O'Brien. For more on the film's endless future, check out our interview with Andrew Stanton and Kenna Harris.
