The concept involved series protagonist Woody being part of a collectible set, an idea that originated in a draft story titled A Tin Toy Christmas.

Ralph Guggenheim, a producer on Toy Story 2, said that the team took inspiration from 1950s children's cowboy television series, including Howdy Doody and Hopalong Cassidy, to define the rest of the characters in Woody's set: "You would find a gruff old prospector.

Chief creative officer Pete Docter said that the team knew that Woody could not be convinced to leave through logic and reason so they decided that it needed to centre on a relationship: "Jessie brought this sense of responsibility and duty".

He said that several attempts were made to create the scene in which Jessie tells her backstory but when this failed to work, they found that it was better expressed through the song "When She Loved Me", written by Randy Newman and performed by Sarah McLachlan.

He was tasked by the Pixar team to write a song that would explain Jessie's relationship with her owner and her sadness when the girl grew up.

[7] In the fictional 1950s series "Woody's Roundup", Jessie's yodelling voice is provided by Mary Kay Bergman.

This valuable toy collection is destined to be sold to a museum in Tokyo by a collector named Al McWhiggin.

[2] After making friends with Woody and the other toys, Jessie's outgoing personality returns and she develops a romantic attachment to Buzz Lightyear.

Upon discovering that he and the others will be sold to a toy museum in Tokyo, Woody tells them that he must get back home to his owner, which causes Jessie to become enraged due to her fear of being kept in storage.

He eventually decides to go back to his owner and asks Jessie and Bullseye to come with him, but Stinky Pete will not let them leave and the group is taken to the airport.

Following another rough play date with the young children, Andy's toys are reunited with Woody, who has a change of heart and decides to rescue his friends.

When the toys get stuck in a garbage truck along with Lotso, Jessie is rescued by Spanish Buzz, who appears to be crushed by a broken television set.

Jessie was confirmed to be appearing in the upcoming film Toy Story 5 in an image revealed at Disney's D23 Expo.

[14][15] Jessie was featured as a minor character in Toy Story That Time Forgot, a television special for ABC.

[28] Jessie appears as a towering figure above Toy Story Land at Walt Disney World, Orlando.

[31] In 2022, Jessie's Trading Post Store and Roundup Rodeo Barbecue opened in Toy Story Land at Disney's Hollywood Studios.

[33] Disney heavily promoted Jessie following the release of Toy Story 2, as she was a character that they could market to girls, something the original film did not really provide.

Rolling Stone ranked Jessie as the fifth best Pixar movie character, highlighting Cusack’s "bubbly, fragile performance" and noting that in her song "When She Loved Me", she epitomises the end of childhood.

Club summarised Jessie's abandonment by her owner as "gut-wrenching" and a "sobfest", commenting that parents would especially feel the emotional impact of the loss of childhood innocence.

[40] In a review of Toy Story 2, Roger Ebert described Jessie as "spunky" and "liberated", commenting that "she brings new life to the cast by confronting the others for the first time with a female character who's a little less domestic than Mrs.

[42] Jessie has been described as a "strong, independent and assertive female character",[43][44] though Lilian Munk Rösing described this strength as "boyish" and "manic".

[45] Matthew Wilkinson of Screen Rant, ranking her as the best supporting character in Toy Story, stated, "Jessie really brought the girl power into the franchise in a big way.

[50] Ella Alexander of Harper's Bazaar noted that in Toy Story 3, Jessie is pushed to the background except for her scenes involving her romance with Buzz Lightyear, while in Toy Story 4, she is again given a minor supporting role in favour of Bo Peep: "It is, for Pixar at least, too much of a stretch to feature two women in key roles.

[53] Time writer Stephanie Zacharek noted the significance of Woody handing over his sheriff badge to Jessie in Toy Story 4, commenting, "the reign of the white man is coming to an end".

Marc Snetiker of Entertainment Weekly remarked on her "fizz-pop-crackle twang" and considered Jessie to be "one of the most fully realized and precisely layered characters on Pixar’s roster".

[56] MovieWeb writer Katey Hicks ranked Jessie as Cusack's best performance commenting that she creates a convincing and heartbreaking portrayal of the character.

[58] Jessie also received the Patsy Montana Entertainer Award from the National Cowgirl Museum and Hall of Fame.