- Parachuting Instructor (voiced by Gregg Berger)
- Stupid Announcer (voiced by Neil Ross)
- Wilbur Entwhistle (voiced by Gregg Berger)
- Jackson Freen (voiced by Neil Ross)
- Oliver Wendell Funnyname (voiced by Thom Huge)
- Madman Murray (Non-speaking cameo)
- In the skiing footage of Jon in Great Moments of Stupidity, two of the people resemble the skiing woman and the skiing lodge manager from the episode Break a Leg.