In this episode of I Want That Too, Jim Hill and Lauren Hersey unpack what Disney’s upcoming Toy Story 5 might really be about - and why it hits closer to home than you think. From Woody’s absence to Jessie’s promotion, and a new iPad-inspired character named Lilypad, this fifth entry isn’t just a sequel - it might be Disney’s most self-aware film yet.

Jim and Lauren discuss how streaming, AI, and even shoppable shows are reshaping how Disney tells stories - and sells them. They also reflect on the history of Toy Story merch, John Lasseter’s mint-in-box rule, and a deeply personal Jessie doll story that brings it all full circle.

Toy Story 5’s new challenge: an iPad named Lilypad

How Jessie becomes the new Woody in Bonnie’s room

The real reason Toy Story 4’s ending felt like closure

Disney’s experiments with QR codes, GoPuff, and “Shop the Stream”

The merchandising legacy of the Mickey Mouse Club

Jim’s personal story of meeting John Lasseter with his daughter’s Jessie doll

Whether you’re team Woody, team Jessie, or team “Do we need another sequel?”—this episode will give you plenty to think about.

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