Cover Taylor Swift’s new song ’I Knew It, I Knew You’ continues Jessie’s story from ‘Toy Story 2’ (Photo: Disney)
Taylor Swift’s new song ’I Knew It, I Knew You’ continues Jessie’s story from ‘Toy Story 2’ (Photo: Disney)
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From the weeping cowgirl Jessie to the Taylor Swift country comeback, the ‘Toy Story’ franchise has always known how to break us—and put us back together again
The moment Taylor Swift heard an early cut of Toy Story 5, she knew exactly what to write. The result, ’I Knew It, I Knew You’—released on June 5—is a country-pop original co-written with Jack Antonoff, and it centres on everyone’s favourite cowgirl, Jessie. It is a poetic full-circle moment: in 1999, Sarah McLachlan devastated us with Jessie’s story of abandonment; in 2026, Swift is here to heal it.
From Sarah McLachlan to Taylor Swift: the musical evolution of Jessie the cowgirl
Toy Story 5, directed by Pixar veteran Andrew Stanton, shifts its emotional spotlight firmly onto Jessie. The film’s central conflict sees the toy gang—led by Woody (Tom Hanks) and Buzz Lightyear (Tim Allen)—competing for Bonnie's attention, who has become consumed by an addictive tablet called Lilypad. It is Jessie (Joan Cusack) who steps forward to navigate this digital disaster, making her the franchise’s emotional compass for the first time since her shattering introduction in 1999. Swift, who has said she dreamed of writing for these characters since watching the original film at age five, was the perfect artist to close that arc.
As her new track rewrites the emotional map of the franchise, here are the Toy Story songs that defined our favourite toy characters’ journeys.
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‘Woody’s Roundup’ (1999)
Above A rousing Woody and Jessie number from 'Toy Story 2'
A gleefully infectious slice of fictional television nostalgia, “Woody’s Roundup” is a high-energy country throwback that celebrates Jessie and Woody’s shared vintage TV lore. Written by Randy Newman and bursting with honky-tonk energy, it establishes the duo’s roots in a shared cultural mythology—and reminds us that, long before Bonnie’s living room, these two cowpokes had a whole imagined universe of their own.
‘I Can’t Let You Throw Yourself Away’ (2019)
Above Woody tries to save Forky in 'Toy Story 4'
Bouncy, brassy and brilliantly comedic, this big-band jazz number underscores a montage of Woody repeatedly rescuing the newly made Forky from rubbish bins. Written and performed by Newman, it captures Woody’s fierce, almost compulsive loyalty in the most delightfully absurd fashion. Director Josh Cooley, who personally pitched the story to Newman at his home, described the collaboration as essential: he simply could not imagine making a fourth film without him.
‘Strange Things’ (1995)
Above Randy Newman’s ‘Strange Things’ captures Woody’s jealousy in ‘Toy Story’
Deceptively upbeat, “Strange Things” is Randy Newman’s pointed pop-rock meditation on professional displacement. As Buzz Lightyear steals Andy’s affections, Newman’s wry observations expose Woody’s insecurity with surgical precision. It is perhaps the franchise’s most psychologically honest track—a cheerful tune about a very uncomfortable feeling that any adult listener will recognise immediately.
‘The Ballad of the Lonesome Cowboy’ (2019)
Above Chris Stapleton performs the country anthem from ‘Toy Story 4’
Chris Stapleton’s traditional country offering gives Woody a rare moment of wide-open liberation. Written by Newman and performed by Stapleton with warm acoustic and slide guitar, the track reframes Woody not as a toy left behind but as a cowboy stepping freely into the world. In retrospect, it reads as a direct stylistic ancestor of Taylor Swift’s newest contribution.
‘You’ve Got a Friend in Me’ (1995)
Above The iconic theme song of 'Toy Story' celebrates Woody and Andy's bond
“You’ve Got a Friend in Me” is the anthem that started it all. Warm, ragtime-inflected and irresistibly singable, Randy Newman’s Oscar-nominated theme has transcended the franchise to become one of cinema’s most recognised songs. It is not merely a theme—it is a statement about loyalty, belonging and the kind of friendship that asks nothing in return. Decades on, it still hits like the first time.
‘I Will Go Sailing No More’ (1995)
Above Buzz confronts a heartbreaking truth in 'Toy Story'
One of the most quietly devastating songs in animated film history, this sweeping orchestral ballad accompanies Buzz Lightyear’s crushing realisation that he is a plastic toy—not a space ranger. Newman’s soaring strings and piano carry the full weight of that existential collapse, making it remarkable that this level of emotional nuance existed in a children’s film released in 1995.
‘When She Loved Me’ (1999)
Above Sarah McLachlan's 'When She Loved Me' remains the most emotional moment of 'Toy Story 2'
“When She Loved Me” is still the franchise’s most devastating sequence. Written by Newman and performed by Sarah McLachlan across approximately 17 takes at The Warehouse Studio in Vancouver, the song transformed Jessie’s backstory into biography. McLachlan wept at Newman’s simple piano demo; Tom Hanks and Tim Allen reportedly did the same during an early screening. The track won a Grammy, earned Golden Globe and Oscar nominations and has never stopped making grown adults cry.
‘I Knew It, I Knew You’ (2026)
Above Taylor Swift’s new country-pop song heals Jessie’s heart in ‘Toy Story 5’
Taylor Swift’s first country-format single since 2021 is, by every account, the emotional sequel to “When She Loved Me” that Jessie fans have long imagined. Co-written and co-produced with Jack Antonoff, the track is built around acoustic strings and Swift’s instinctive narrative songwriting, arriving just two weeks before Toy Story 5 hits cinemas on June 19. Yet what has made “I Knew It, I Knew You” especially notable is the reaction it drew from the filmmakers themselves.
The word Toy Story 5 director Andrew Stanton used upon first hearing Taylor Swift’s song was “kismet”. He described it as a “long-lost family member”, praising how naturally it fit within the world of Toy Story. Swift’s understanding of Jessie’s emotional journey was so instinctive that the song seemed to complete a thread the franchise had been following for decades. As “I Knew It, I Knew You” arrives, audiences will get their first glimpse of how the song fits into the next chapter of Jessie’s story.
After more than a decade in lifestyle media, Clifford has mastered the art of writing seriously about things that are fun—and writing fun things about people who take themselves very seriously. At Tatler Asia, he helped steer its flagship lists, Tatler’s Most Influential and Asia’s Most Stylish. And today, he leads T-Labs, Tatler Asia’s content innovation hub, where he continues the noble pursuit of lifestyle storytelling, spinning stories on wealth, entertainment, necessary style, Hallyu, Hollywood, beauty and more for audiences across Asia.
