After the school bus is destroyed at the auto wrecking yard, Homer is forced to drive his (and other) kids to school. Along the way, he listens to a classic rock radio station that plays "Shinin' On" by Grand Funk Railroad and is shocked to discover that all of the kids hate it, and have never heard of them. After several more days of the kids hating his music (which Bart calls "dinosaur bands"), Homer visits Good Vibrations music store, which has been renamed Suicide Notes since Homers last visit, and realizes that what he likes is no longer considered cool. Homer reminisces about his teenage years, back when he was cool (though the viewer is shown that Homers actual youth wasn't exactly the thrillride he remembers), and the next day surprises Bart and Lisa when he abandons Milhouse on the side of the road. Instead, he reveals that he's taking them all to the Hullabalooza music festival, a major rock event that was advertised at the music store. At the festival, Homer tries to act cool by wearing a Rastafarian hat, but all he does is humiliate himself and is confronted by an angry crowd of Generation Xers who mistake him for a narc. After being tossed out by the crowd, Homer angrily kicks a cannon, which shoots one of Peter Frampton's inflatable pigs (purchased at "Pink Floyd's yard sale") at his stomach. However, Homer is seemingly not hurt by the impact; the festival head is impressed and Homer is hired as a part of the festival's freak show, much to Marge's annoyance.
As a result, Homer gets to go on tour with the festival and hangs out with The Smashing Pumpkins, Cypress Hill and Sonic Youth. Homer suddenly finds himself living the high life: partying with big name rock stars and becoming respected among American youth, including Bart. As the tour approaches a stop in Springfield, Homer's stomach begins to hurt and he is sent to a veterinarian. The veterinarian advises Homer that if he performs his act one more time, his stomach will burst and he will die. Homer shrugs this news off, not wanting to lose his popularity or the newly won respect of Bart. At first he decides to do his job, but at the last second he loses his nerve and dodges the cannonball. Consequently, he is released from the festival and, despite a warm sendoff from the rock stars, goes back to not being respected by his children, though he now no longer cares about "looking cool" in front of them, having learned that someone who is cool doesnt feel the need for constant validation.