Joan Cusack, the voice of Jessie in Toy Story 5, recently visited Magic Kingdom to check out the new show at Diamond Horseshoe, called Jessie’s Roundup.

Jessie’s Roundup

The official film description states, “Buzz, Woody, Jessie and the rest of the gang’s jobs are challenged when they’re introduced to what kids are obsessed with today….electronics!” Toy Story 5 comes out on June 19, 2026.

Cusack wears a button-down shirt with horses and a jean skirt—appropriate for a visit to Frontierland! She joins her palls Jessie and Woody in the venue. Watch the video below:

During her visit, she surprised Jessie’s Roundup Cast Members and even yodeled with them!

Diamond Horseshoe hasn’t had a show in over 20 years, but that has changed with Jessie’s Roundup. It’s part of Cool Kids’ Summer at Walt Disney World to promote the release of Toy Story 5.

The interior of the Diamond Horseshoe is decked out in Toy Story decor, most of which references the Woody’s Roundup television show introduced in Toy Story 2 as the origin for Woody, Jessie, and Bullseye.

The show portion of Jessie’s Roundup has two distinct parts: one with a live singer on guitar featuring Bullseye, and another with dancing and a jump rope act starring Jessie and Woody.

Learn more about the show and watch our POV video below:

Jessie’s Roundup will be offered through September 8, 2026 for Cool KIDS’ Summer at the Magic Kingdom, following that the Diamond Horseshoe will return to being a table service dining venue.

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