In the films, Jessie is the deuteragonist of Toy Story 2, the tritagonist of Toy Story 3 and a supporting character in Toy Story 4.
In the TV specials, she was the protagonist of Toy Story of Terror! and a supporting character in Toy Story That Time Forgot.
She is voiced by Joan Cusack, while Mary Kay Bergman did her yodeling voice and television voice in Toy Story 2, and while Sarah McLachlan did her singing voice.
Jessie is an excitable and tomboyish cowgirl doll. She is slender and fair-skinned in plastic. She has green eyes, red hair with a ponytail in braids and a yellow ribbon that is tied to the bottom of her ponytail, pink lips, a white long-sleeved western-style shirt with both yellow blouse and cuffs that have red doodles, blue jeans, a belt with a gold buckle, a pair of chaps that have cow spots all over, brown cowgirl boots, crimson cowgirl hat, and a pull string on her back with a white loop attached to it.
She likes being loved by any other child and has a power to yodel. She hates being in storage as it makes her claustrophobic or afraid of enclosed areas and not having someone to love her. In her story that she is telling Woody about, her first owner was Emily just before she got donated by her when she was a young adult. Then, her next owner was Andy Davis at the end of the 1999 film, and she becomes Buzz Lightyear's love interest. At the end of the third film in the saga, she, along with both her boss and significant other and the rest of Andy's toys, now belongs to Bonnie Anderson, a little girl who attends Sunnyside Daycare.
Jessie was once owned by a little girl named Emily. 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. However, years have passed, and Emily has found more mature activities to do, forgetting about Jessie until finding her under the bed one day. 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. Eventually a man named Al McWhiggin found her and took her back to his apartment where Jessie met Bullseye and Stinky Pete. Being in a box for a long period of time, Jessie has developed claustrophobia or a fear of enclosed areas.
Toy Story 2
I'm not going back into storage!
~ Jessie refuses to go back in storage
In Toy Story 2, she is the second toy that Woody meets in Al McWhiggin's apartment after Bullseye and before Stinky Pete the Prospector. She is sassy, sweet, cute, athletic and has a habit of yodeling when happy or excited. However, when Woody reveals that he still has an owner named Andy 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 then begins to mock Woody for still having an owner. 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, accuses Jessie for turning on the TV, to which Jessie responds by fighting Woody. The Prospector breaks the fight, and Jessie still feels bitter about Woody caring only about Andy. 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. When Woody talks to Jessie, she tells him the story about Emily. After hearing that story, Woody initially starts to leave, but with more of the Prospector's convincing, Woody, thinking that 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 brighten up to happiness and excitement. Soon Buzz Lightyear, Rex, Hamm, Mr. Potato Head, and Slinky Dog arrive (with another Buzz Lightyear) to recuse Woody and Potato Head tries to attack Jessie but fails. Upon seeing Slinky growl at Bullseye, Jessie orders him to stop and Slinky wraps his string around both of them. When Woody offers to take the Roundup Gang with him back to Andy's house after having a change of heart and deciding to go back to Andy's room with Buzz and the other toys, Jessie initially feels uncertain. But Stinky Pete, now showing his true colors, locks them in Al's apartment. Woody and Jessie try to stand up to the Prospector, but they learn that the Prospector has never been sold from a dime store shelf, which makes him feel more determined to get himself and the others to Japan, where he believes he will finally be appreciated. At the airport, Buzz and the toys extricate Woody and get rid of the evil Prospector, but are unable to free Jessie from the case, despite Bullseye being able to escape, as the case gets loaded into a plane bound for Japan. Determined to rescue Jessie, Woody whistles for Bullseye, and he and Buzz mount and gallop across the airfield to rescue Jessie. Woody, after being separated from Buzz again, follows the case into the plane's cargo hold. There, Woody again offers to take Jessie back to Andy's house. She initially fears that Andy will not like her, but Woody tells her that it will not be so bad because Andy has a baby sister. Excited, she agrees to go with Woody (and the other toys), but the two become trapped in the plane. Finding another escape route, they exit the plane. But Woody slips, prompting Jessie to grab hold of Woody's arm. Using his pull-string, Woody and Jessie swing down from the plane and land on Bullseye right behind Buzz, finally completing the mission just seconds before the plane takes off. As they celebrate their success, Jessie describes Woody rescuing her as "Woody's finest hour". Back at Andy's room, when Andy comes home from Cowboy Camp, he is pleased to see Jessie and Bullseye added into his toy collection, calling them Bazooka Jane and her jet-propelled horse. With Andy's name printed on the bottom of her boot, Jessie is overjoyed to feel appreciated again. Buzz clearly, but nervously, develops a crush on her and the two enter a relationship somewhat similar to the way Woody and Bo Peep have done. The two couples are seen standing together as they enjoy watching a newly-fixed Wheezy sing "You've Got a Friend in Me".
Toy Story 3
Andy's moving on, Woody. It's time we did the same.
~ Jessie leaving for Sunnsyide
10 years after the events of Toy Story 2, Jessie returns in Toy Story 3 where she is still living at Andy's house with his other remaining toys - Woody, Buzz, Bullseye, Rex, Hamm, Slinky, Mr. Potato Head, Mrs. Potato Head and the Little Green Men. Jessie continues to have fond affections toward Buzz. When Andy attempts to put her and the other toys in a bag in the attic, she and the others do not realize that his mom accidentally threw them out. Luckily the toys escape the bag. To keep herself from reliving the traumatic life she had when thrown out by Emily, Jessie convinces the other toys they should go to go to Sunnyside Daycare. There Jessie shakes hands with Chunk and is excited when Lots-O' Huggin' Bear tells that the children at Sunnyside are replaced with new children when they get older, meaning that they will always be played with no matter what. She tries to convince Woody into staying, but he turns down the offer and calls her 'selfish', leaving to go back to Andy alone. This hurts Jessie. After recess ends, she and the other toys realize that they have been put in a room where the children that, roughly but innocently, abuse them and are too young to even handle them. One of them uses Jessie like a paintbrush. Later, after Buzz disappears to talk to Lotso, Mrs. Potato Head sees Andy with the eye that she left in Andy's room. Jessie and the other toys realize that Woody was right, that Andy still wanted them. They decide to return home to Andy but are imprisoned by Lotso, who had Buzz reprogrammed and think that he is a space ranger again, turning him against them. Buzz sets down the prison rules, and in order to make sure they obey them, Lotso gives them a warning and tosses them Woody's hat (which he left behind). This causes Jessie and her friends to think Lotso killed Woody. The next morning, Jessie and Bullseye are the ones who have been mourning Woody's apparent "death" the most. When Woody returns to rescue them, after hearing a sad story about Sunnyside and Lotso by one of Bonnie's toys named Chuckles, Jessie and the others are super happy to see that he's still alive and give him his hat. Jessie apologizes for not listening and Woody apologizes for leaving. They make a plan to escape and Jessie is soon reunited with Buzz, who had been reset to the Spanish mode of his space ranger self; a romantic version of Buzz who is far more outspoken about his feelings for Jessie (the reset had temporarily erased his memories). At first, she is uncomfortable with the change but finds that she also rather likes this romantic version, too. When they get stuck in a garbage truck, Buzz saves Jessie, but is soon flattened by a television. Thinking that he is dead, she starts to despair but Buzz reawakens to his normal self, not remembering a thing that happened before. Jessie kisses Buzz, happy he is alive. They soon fall into a landfill where the squeeze-toy aliens, who had run off to a giant "claw", are. When the toys escape the shredders, Jessie grabs a watch. After Lotso leaves Jessie and her friends to die at an incinerator, Jessie joins hands with Buzz and Bullseye. As the toys accept their fate of doom, they are saved by the aliens who used the claw they saw. Afterwards, Jessie notices Buzz is still holding her hand, and they both smile at each other. Soon They all return to Andy's house, however Woody has Jessie and the others donated to Bonnie, the girl that found Woody outside of Sunnyside. Jessie and the others are all played with by Andy one last time and she quickly adjusts to her new life with Bonnie. Towards the very end, she takes advantage of Buzz's new Spanish side and they dance together to "Hay Un Amigo En Mi" (the Spanish version of "You've Got a Friend in Me").
Toy Story 4
We're not going anywhere, if you get my point.
~ Jessie after puncturing the tires on the Anderson RV.
Jessie returns in Toy Story 4 as a supporting character. Nine years prior to the events of the film, Jessie helps Woody, Buzz and the other toys rescue RC from being washed away in the rain. She is then seen in the present as one of the toys being chosen over Woody during Bonnie’s playtime. Bonnie takes Woody’s badge and pins it on Jessie to have her fulfil the role of sheriff instead.
Later in the film, During a road trip to a travelling carnival, Woody and Buzz are absent from the family RV as Bonnie’s parents attempt to leave carnival early. Not wanting to leave he friends behind, Jessie grabs a nail and quickly punctures the vehicles tires before making it clear to the other toys that they were not going anywhere.
That night, Jessie joins the rest of Andy's old toys in saying goodbye to Woody, who had decided to stay with Bo Peep at the carnival and travel the world. Woody gives Jessie his sheriff badge to take over his leadership role alongside Buzz Lightyear.
Buzz Lightyear of Star Command
Jessie made silent cameos during the intros of Buzz Lightyear of Star Command.
Buzz Lightyear of Star Command: The Adventure Begins
In the show's pilot, Jessie made a silent intro cameo appearance in the film's opening sequence, walking alongside Buzz as they inspect the recently arrived VHS copy of the video. Despite not speaking, she makes a quiet giggle.
Toy Story Toons
In Hawaiian Vacation, after the toys come up with an idea of recreating Hawaii for Barbie and Ken, who have unexpectedly revealed themselves in Bonnie's room, Jessie acts as one of the Aloha Spirits, greeting Ken with an enthusiastic "ALOHA!". When Barbie and Ken are having their "dinner," she seems to be the assistant waitress. In Small Fry, Jessie and the others want to know what happened to Buzz after Mini Buzz arrives. She is seen looking pretty impressed with Mini Buzz's tricks as he skates around the room, but is quickly annoyed after he takes Woody's hat and annoys the others. Later in the episode, Mini Buzz attempts to flirt with Jessie with no luck. She is last seen when Buzz returns to the room. She gives him a big hug and exclaims "You're back!" In Partysaurs Rex, she is seen holding the toy fan that made Mrs. Potato Head's bubble bigger, and shields herself with it when Rex bursts the bubble. She then joins the other toys (except Woody, Buzz, Bullseye, Hamm, Dolly and Mr. Pricklepants) in calling Rex "Partypooper Rex", and runs away with them when Bonnie comes. Later, Jessie is seen with Woody, Buzz, Mr. Potato Head, Hamm and Mr. Pricklepants as they walk towards the bathroom door, wondering if Rex was okay, only to be hit by the overflowing bathwater bursting the door open. At the end, she was using the same toy fan to dry Mr. Pricklepants being held by Buzz, and sighs when Rex says that he was a "Partysaurus". She then watches with the other toys as Rex helps to turn on the outside faucet for the pool toys to have them party after hearing of Rex's exploits from the bath toys.
Toy Story of Terror!
Jessie didn't give up. Jessie found a way.
Jessie returns in the Toy Story Halloween special Toy Story of Terror! as the protagonist. She is seen on a road trip with Woody, Buzz, Rex, Mr. Potato Head, Mr. Pricklepants and Trixie. During the road trip, she is trapped in a small tool box. They stay in a motel for the night with the Andersons. When her friends are stolen by the motel's owner along with some other toys, it's up to her to save them from being shipped to a toy collector, and to do that she must conquer her claustrophobia.
Toy Story That Time Forgot
Jessie return in the Toy Story Christmas special Toy Story That Time Forgot with a much smaller role.
Jessie makes a cameo appearance in Monsters, Inc.
Jessie was originally going to be a toy cactus named Señorita Cactus and would have been revealed to be an antagonist alongside Stinky Pete, but the animators changed her character to a cowgirl heroine after it was suggested the main cast needed a energetic female lead.
Jessie was originally going to be voiced by the late Mary Kay Bergman, but Bergman died of a gunshot wound before the role was given to Joan Cusack.