Garfield hosts a show called "Great Moments in Stupidity", where he follows Jon Arbuckle, who has taken up skydiving.
One day in the house, Garfield is in bed complaining that everyday is the same boring day. He goes into a new position when Jon comes in complaining about the same thing. After a while, Jon declares that he will take up skydiving, much to Garfield's shock. This leads to the start of the show "Great Moments in Stupidity."
The announcer of the show introduces Garfield, who explains that "Great Moments in Stupidity" shows all the stupid people in history. These people include Wilbur Entwhistle; who spent 37 years thinking of another name for ketchup, Jackson Freen; who spent his entire family fortune on toast, and Oliver Wendell Funnyname; who was stranded on an escalator for 19 hours due to a power failure. He then states the most favorite of them all is Jon Arbuckle and shows various clips of Jon's memorable stupidest moments. The announcer then shows a preview of next week's show dedicated to dogs before going to Jon's skydiving.
At the airport, Jon is preparing to skydive though Garfield bets he will not survive, even asking for the keys to the house. On the plane, Jon has second thoughts making the parachuting instructor throw him out. As they are falling, Jon attempts to pull various ripcords, all of which fail. In desperation, Garfield manages to pull a secret ripcord which causes the chute to open and Jon's pants to fall down.
Recovering from the experience, Jon promises Garfield never to do anything stupid again. Garfield does not believe that comment, promising they will have more exploits of Jon on "Great Moments in Stupidity". Jon then says that he will take up bungee jumping.
- Parachuting Instructor (voiced by Gregg Berger)
- 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 "Break a Leg".