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 trousers.
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. Jessie then spends one last ride in a car with Emily, just like what once occurred when she was younger, but as she (now seen to be older as she can drive) steps out, she dumps her old toys, including Jessie, into a charity box, and Jessie watches in shock and sorrow through a hole in the box to see Emily drive away. 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.
As the toys believe Andy has thrown them away, Jessie mentions Emily by saying, "It's Emily all over again!"
- The tree with the tire swing where Emily takes Jessie to is the same tree from Ant Island in A Bug's Life.
- The car Emily is driving is the same one that Jessie uses to help Buster "relieve himself" at the end of the movie.
- Emily is mentioned once again in Toy Story 3 when Jessie faces her fear of being thrown away again by Andy.
- There is a remote possibility that Emily is actually Andy's mom. She has the same physical build, hair color, and is the right age. (She is seen wearing 50s style saddle shoes, has 60s decorations in her room, and later drives a 70s-era car that Buster uses to relieve himself. She presumably got Andy his Woody doll, even though Woody's Roundup was long since outdated, and she showed no surprise, at least on screen, at seeing Jessie and Bullseye when they became Andy's toys.) Although, if she was born sometime in the early 50s, that would mean she is in her early 40s during the movies.
- Emily also had a life-size replica of Jessie's hat that is the exact same one which Andy owns, giving another reason towards the possibility of Emily being Andy's mom.
- There is also an alternate ending where Emily's car keeps crashing in.
- It is possible Emily remembered about Jessie all along (but had other things to do). It should be noted that, if she really did drop all those Jessie accessories, she would and should have remembered her.
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