As Goofy cleans the house, Max complains to P.J. that his dad can't afford to take them on a nice vacation like Pete can. After Goofy has an unpleasant experience with the vacuum cleaner, the boys realize that they can record him and submit the video to win a free vacation to Hawaii from "America's Most Painful Home Videos".
Pete catches the boys using his camera to film Goofy and forbids them at first. When Max explains that they are attempting to win a free $10,000 vacation, Pete reconsiders and decides to help them get the footage by the midnight deadline.
Pete and the boys observe Goofy sleeping on his hammock. Pete tells him he needs to clean out his gutters before a storm hits, as he imitates the sound of thunder and sprays a hose over the fence. Goofy slips and gets caught in the hammock as Max records him.
Later as Goofy is cleaning the gutters, Pete tries to cut Goofy's ladder down. When Goofy asks him to help remove a bird's nest, the mother bird flies in and attacks Pete, knocking his ladder over. Pete gets thrown into some power lines, shocking him and sending him flying.
Over at Pete's car lot, Pete builds "Evel Boll Weevil's Torture Ramp of Death", a giant roller coaster-type ramp on which he asks Goofy to paint a stripe on. He affixes Goofy with skates and a rocket pack and sends him flying at high speeds down the ramp. Goofy does some loops and crashes through a few walls as Max gets it all on film. At the end of the ramp, Goofy triggers an explosion and launches into the air. Pete sets up a wet cement bucket and Goofy's head gets lodged into it, creating a perfect cement copy of Goofy's head.
Pete retrieves the tape from Max and P.J., telling them he will get it to the TV station before the deadline. As he leaves, he kicks a bucket, which knocks his entire ramp down onto him.
On TV, the host of The World's Most Painful Home Videos introduces a clip, as Max groans that he hasn't heard back from the show yet. Just then, the winner of the vacation is announced to be Goofy! On the show, Pete walks through the door wearing the cement head of Goofy to claim the prize for himself. Peg and Pistol recognizes Pete in disguise and Max gets furious. Peg assures them that she will yell at him when he gets home.
When Pete arrives, Peg yells at him about how angry she is with his actions. He claims he did he for her and the kids, but she tells him to give the tickets back to Goofy or he'll be going on their summer vacation alone. When Pete doesn't listen, everyone plans a scheme to get back at him.
Max and P.J. tie Pete to a chair and Goofy flies in from above dangling from a rope, waking Pete up. Goofy claims to be a ghost and that he died drowning in his own fishing bucket because he was forced to take another backyard vacation.
He then tells Pete there are more people affected by his villainy, as Pistol spins his chair into the next room "sending him into the future". The next "scene" shows Max running Pete's Used Car Lot in the future, with Peg as his maid. They talk about how Max stole Pete's business and that Peg works for only three cents an hour. Just then, Max clicks on the TV to the breaking news host Goofy reporting that "Scarlet P.J." and "Pistol-packing Pistol" are being cornered in an alley.
As they fake their deaths, Peg and Pete both sob uncontrollably. Pete breaks free from the chair and cries for his children. He apologizes to Goofy and promises to give back the vacation and make it up to everyone if Goofy will help him avoid this future, to which he agrees.
Later on vacation in Hawaii, Max beckons for Pete to bring him more lemonade. When he refuses, Goofy scares him, reminding him of his ghost encounter. Pete quickly brings him the drink while the rest of the families laugh at him.