Season Four Premiere. Kevin and Jack attempt to keep count of all of the dreams that Disney attempted to grant during a strange mid-2000s promotional event.

Season Three Finale. In the long-awaited conclusion to this season, Kevin and Jack are joined by Dan and Rob for a surreal and somewhat dark exploration into what Walt Disney's Carousel of Progress would be like if John Progress were real and also depressed.

Kevin asks Jack if he recalls the 2010-era rock band OneRepublic, and the two embark on a journey filled with several realizations and a lot of bad singing.

In this episode, Kevin recalls his childhood trip to Cripple Creek, Colorado and relays the action-packed history of the town to Jack.

Jack introduces Kevin to a new book by the former dean of Disney University, prompting Kevin to discuss his thoughts on motivational speakers.

Jack tells Kevin about an obscure theme park named Fun Junction USA that had a bit of trouble getting off the ground.

Season 3 Premiere. Kevin reads Jack and Rob several news stories from the early days of Disneyland, showcasing the peculiar issues that the park's security force encountered.

Season Two Finale. Kevin and Jack fall down the rabbit hole of the palm tree fandom and their strange relationship with Walt Disney World.

Jack encourages Kevin to dive into the history of Central Florida's famous Gatorland.

Kevin tells Jack about Star Wars Weekends at Disney's Hollywood Studios and one specific show that was performed during the event.