Shane and Jason are joined by Chris Meek for their fifth annual May the Fourth episode of the podcast. The group chats about Blue Milk, Batuu, Video Games, and the TV offerings from the past year. Shane pays tribute to his friend Jedi Master Samir Samoris, who recently became one with the force.

Shane and Jason are joined by Jason Richardson and Troy Myers to do a Music Draft of songs from 1999. Shane takes his obsession with 1999 to a new level, when he picks seven categories, and asks the guys to attempt putting together the best "Side A Mix Tape" for music that was released in 1999. This leads to a heated debate over The Backstreet Boys' "I Want it That Way".

Shane and Jason go on a magical dude's vacation with some friends to Walt Disney World, where they enjoy riding the movies and geeking out with all things "Star Wars" related at Smuggler's Run, amongst other destinations. They share photos and stories form their adventure, after they discuss some Community Poll Results, and other Disney-themed topics.

The guys get together for a mini-episode to celebrate Valentine's Day. They discuss the Grammys and the Super Bowl, before moving into the topic of fictional romances that took place in action movies. They talk about their favorite girls for Indiana Jones and James Bond, and then pick their Mt. Rushmore based on the films they've discussed.

It's a tangent-filled episode, as Shane and Jason add a new section to the show: Music of 1999. After discussing some albums and telling stories, they give their Mt. Rushmore of fictional couples, before they discuss recent films that did NOT live up to their expectations, but they talk about the films that surprised them by exceeding what they expected. Troy Talks features a discussion on Troy's artistic project: Penguin of the Day.

Happy New Year from Shane and Jason. To kick off the new year, the guys take a look back at the films they watched in 2023, and it gets rough for them to pick out four films they actually liked last year. After they take a break for Troy Talks, they come back and announce some of the creative projects they plan to work on over the next two years.

Shane and Jason wrap up 2023 with a Christmas Special, looking back on the year and discussing some of the things they were most excited about. The guys wrap things up by resurrecting Shane's Christmas Mix tradition from the past, and creating a new 2023 Mix, with some help from a few special friends, which Shane then publishes on Apple Music.

Shane and Jason welcome back Jason Richardson and Chris Schneider for a Clearwater 12 Reunion. From movies, to music, to television, the guys reminisce about the things that hold special places in their hearts and minds. During Troy's Halftime Talk, Troy points out the irony that most episodes of the podcast are actually nostalgic on their own.