Jarrett Lennon Kaufman (Jett to his… let’s say “friends”) returns to his old hosting seat to ask the big question, “What's the luckiest you've ever been?” Stephen immediately makes everything more difficult, but almost makes up for it with his game show fortune! We find out why teachers should never be allowed money, theater kids’ secret addiction, what happens when the Justice League thinks “Indestructo” needs to seek alternate employment, how Jett turned someone else’s wedding into a career opportunity, and just how long is too long to sit at a slot machine!

Cast: Sean Michael Boozer, Chris Compton, Michael Heiman, Stephen C. James, Jarrett Lennon Kaufman, Josh Spence 

Ads: WashclothSteve Circleshirt (improvised by Michael Heiman off of the prompts: Mango on a riverbed, trout tacos, Carmobile, Fishfishing, Frank Stallone, documentary)

Original release date: 5/13/26 

Intro and outro music credit to Matt Walker