In the song "When She Loved Me", Jessie tells Woody that she too once had an owner, named Emily, who was presumably a fan of Woody's Roundup. Emily was brought up by Jessie when Woody had tried to explain to her that Andy is someone very important to him, as she knew what he was going to say to her.
In a flashback, Jessie is first shown sitting on a bed as Emily, first seen as a young girl, puts on her cowgirl hat and takes Jessie on a ride on her toy horse. Then there is a nighttime scene where she is playing with her while she's under her cover in bed. She then takes her out on a drive to a tire swing hanging from a tree on top of a hill, where Emily swings her around. Emily then spins around with her some more, falling into a pile of leaves. Then the scene cuts to Jessie back on Emily's bed, leaning against a pillow. Emily takes it, causing Jessie to fall under the bed, and she watches in despair as Emily, throughout the years, finds more grown-up activities to do (hinted by make-up and music replacing horses and cowgirl-themed toys, as well as Emily talking with her friends in person or on the telephone). At the same time, it is easy to tell that Emily is growing up as well. The scenes also suggest the 1950s, when westerns were popular, then progresses into the 1960s as colorful acid rock posters adorn her room. Another reference to the 60s is seen when a teenage Emily is seen wearing flare-legged pants.
As the years pass, the underside of Emily's bed becomes littered with her old, childhood toys and they, along with Jessie, even carry a coat of dust to show their untouched status. Just as Jessie feels like she has been forgotten, Emily reaches under the bed to find her, feelings of happiness welling inside her after years of being neglected, as Emily's makeup kit had been dropped nearby, causing accessories to be rolled under there. Emily smiled nostalgically at her old favorite toy. Jessie then spends one last ride in a car ride with Emily, believing they were together again. Emily even kept Jessie in her purse as a final gesture of affection. This time, sadly, Emily leaves her old toys, including Jessie, into a charity box, and Jessie watches in shock and sorrow through a hole in the box to watch her "whole world" officially leave her. The roots of Jessie's trauma and phobia of abandonment stems here.
Finally, Jessie concludes her story, somberly telling Woody that the toys would never forget owners like Emily or Andy, but the owners forget about them as time wore on, and tells him to just leave before he can say anything more.
- The tree with the tire swing where Emily takes Jessie to is the same tree from Ant Island in A Bug's Life.
- Emily is mentioned once again in Toy Story 3 when Jessie faces her fear of being thrown away again by Andy.
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