In Toy Story 2, the song is sung off-screen by the character Jessie in a flashback sequence, explaining her history. Sarah McLachlan performs the vocals of the ballad, while actress Joan Cusack does the speaking voice of Jessie.
Prior to the song, Woody is trying to make amends with Jessie, who is greatly embittered with his refusal to be sold to a Tokyotoy museum with the rest of the toys; the museum won't take the gang without him, and if not sold, Jessie and the others will be placed in storage, a dreaded place due to her fear of the dark. Woody tells Jessie that, if only she knew his owner, Andy, she might understand why he wants to return to his home. He attempts to explain his bond with his owner to her, but she interrupts him, guessing that Woody's going to say that Andy's a "real special kid" and that Woody feels like he's alive when Andy's playing with him because, even though he's not moving, that's how Andy sees him. Woody, shocked by the accuracy of her statement, asks how she knows that about him. She says simply: "Emily was just the same. She was my whole world."
As the song begins to play, the audience sees that Jessie once had an owner who loved her as much as Andy loves Woody. The flashback shows Emily, her horse-loving young owner, happily playing, laughing, and cuddling with Jessie. The two are clearly inseparable, with Emily even bringing her toy along with her on car rides. Emily's childhood bedroom is designed with a Wild West-equestrian theme of sorts, with figures of horses, toy guitars, cowhide and plaid patterns, and horseshoes decorating the room. Various Jessie memorabilia, like lunchboxes, alarm clocks, and picture frames, also are present in the room; Emily even dresses in plaid shirts, denim shorts, cowgirl boots, and a replica of Jessie's signature cowgirl hat. However, the audience sees that, as the girl grows older into her adolescence, she begins to forget more and more about her childhood interests and begins to explore things like make-up, nail polish, and vinyl records.
Jessie, who once always had a spot on the center of Emily's bed, has now fallen through a crevice and lies underneath it, forgotten. While Emily has once loved playing pretend with her toys, now — as the audience sees from Jessie's point of view beneath the bed — she prefers inviting her friends over, painting each other's nails, listening to music. Jessie lies on the ground, ignored and unhappy, until one day, Emily finds her under the bed for the first time in several years. She takes the toy along with her to share a day on a car trip, like they did when Emily was a child. Jessie finally feels loved and happy once more, as if things will go back to the way they were. The car comes to a stop, however, and their relaxing day together is put to an end when Emily places Jessie in a donations box on the side of the road, to be given away to charity. The shocked Jessie looks on as her owner drives away and leaves her, and the song draws to a close.
Jessie then states: "You never forget kids like Emily or Andy, but they forget you."