Jessie (Joan Cusack) entered the world of Toy Story in Toy Story 2. Jessie was a toy created based on a television program called Woody’s Roundup that starred Woody, Jessie, Stinky Pete the Prospector (Kelsey Grammer), and Bullseye. We also learn that Jessie was once abandoned and tossed by her owner, which is why she ended up with toy collector Al McWhiggin (Wayne Knight).
A Jessie film could either explore more of her Woody’s Roundup character and its origins, or it could go back to Jessie’s days with former owner Emily. The Emily route may seem sad at first, but we know that Jessie eventually gets a happy ending with Woody, Buzz, and the rest of Andy’s toys. It might be interesting to see what happened with Emily and why Jessie was eventually donated. The Woody’s Roundup route is just as interesting because we don’t know the complete story behind the series and those who created it. Maybe the puppets are based on real people, like maybe Jessie was based on the creator’s daughter or something of that nature. We could see the inspiration for the toy Jessie’s story in a movie.