After hearing that story, Woody initially decides to leave, but with more of Stinky Pete's convincing, Woody, thinking the same fate will happen to him as Andy grows up, warms up to the idea of going to the museum, and Jessie's feelings of bitterness and sadness brightens up to happiness and excitement. Being in a box for a long period of time, Jessie has developed claustrophobia and autophobia. Jessie had spent one more time in the car with Emily, only for Emily to place her in a charity box, leaving her shocked and heartbroken that she has been given away. However, years have passed, and Emily has found more mature activities to do, forgetting about Jessie until finding her under the bed one day. Throughout her years as Emily's toy, Jessie has enjoyed being played with, such as being taken for a horseback riding, a drive in her car, and a swing on a tire. When Woody talks to Jessie, she tells him the story about Emily (seen during the ' When She Loved Me' musical sequence), a little girl that had been her owner. The next day, after Woody's arm has been fixed, Jessie sarcastically lets Woody leave, but the Prospector convinces Woody to speak with Jessie to make amends. The Prospector breaks the fight and Jessie still feels bitter about Woody caring only about Andy. That night, after Woody's attempt to retrieve his ripped-off arm has been sabotaged, Woody, having spotted the remote in front of Jessie's case, angrily accuses Jessie for turning on the TV, to which Jessie responds violently by fighting Woody. She then begins to angrily mock Woody for still having an owner.

However, when Woody reveals that he still has an owner and has no intention of going to the Konishi Toy Museum in Tokyo, Japan, with the Roundup Gang, Jessie begins to hyperventilate for fear that she'll go back into storage again. She is energetic, sweet, cute, athletic and has a habit of yodeling when happy or excited.

In Toy Story 2, she is the second toy that Woody meets in Al McWhiggin's apartment after Bullseye and before Stinky Pete. 3.1 Buzz Lightyear of Star Command: The Adventure Begins.

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