Feeling uncool, Homer decides to take Bart and Lisa to the Hullabalooza music festival. But, while feeling more out of place, Homer accidentally takes a cannonball to the stomach. This newfound skill makes him the sleeper hit of the festival, and a hero to Bart but at what cost to his health?
- Amazingly Embarrassing Parents: The whole plot starts going when Homer is one these to his children and they call him out on it and his very antiquated music likes, so Homer tries to make himself cool again by getting tickets for Hullabalooza.
- AM/FM Characterization: Homer's love of old-school rock-and-roll (in an episode produced at the height of Grunge Rock) becomes plot-important because his children find him old-fashioned, uncool, and infuriatingly embarrassing.
- Bait-and-Switch: When Homer's stomach started growling strangely, the tour organizer says "Homer, nothing's more important to me than the health and well-being of my freaks. I'm sending you to a vet."
- UK airings of this episode usually edit out the roadie and Peter Frampton's lines "He's gonna be pissed off." and "You're damn right I'm gonna be pissed off!" just after Homer gets hit in the stomach with the inflatable pig.
- Recent airings have also cut out the scene of Homer standing at the music store's front, due its name being "Suicide Notes: Formerly Good Vibrations" and some drug references (Bart and Lisa associating the smell of pot to Otto's jacket and Otto thinking his shoes are talking) are also cut.
- Broken Aesop: Marge tries to bring out the Aesop that "it doesn't matter if you're cool to people, you need to be true to yourself" and Homer brings up "you don't need other people to tell you that you're cool", but Bart and Lisa shoot them both down and Marge just angrily says that it's impossible to tell what the hell youth wants these days. To further drive the point home, neither of the kids actually elaborate on their own point about what it actually takes to be cool.
- Butt-Monkey: Peter Frampton can't catch a break.
- Cannot Convey Sarcasm: This exchange between two disaffected teenagers.
Here comes that cannon ball guy. He's cool. Teen 2:
Are you being sarcastic, dude? Teen 1: I don't even know anymore
- Celebrity Is Overrated: Parodied towards the end.
- Couch Gag: The living room is bathed in black light, with the Simpsons in fluorescent colors while a hard rock guitar riff plays until Homer turns the light on and the normal music plays.
- Dented Iron: Homer eventually takes so many cannonballs to the stomach that one more would kill him.
- Disco Dan: Homer towards the start.
Homer: Where can I find the latest releases by Bread?
Record Store Clerk: Oldies.
Homer: Oldies? But you've got all the top bands in here.
- Dissimile: When Homer is being introduced in Springfield, the organizer describes him as "The man who embodies everything about rock 'n roll, except the music."
- Everybody Do the Endless Loop: The teenagers dancing during the show. Reused during the ending credits.
- Growling Gut: Homer develops one due to frequently taking cannonballs to the stomach.
- Kevlard: Homer uses his body fat to stop cannonballs when performing in a freak show. His body still accumulates damage over doing this repeatedly, which would have inevitably killed him if he continued.
- Like Father, Like Son: Abe's famous line from Homer's flashback invokes this.
Homer: You wouldn't understand Dad. You're just not with it.
Abe: I used to be 'with it', until they changed what 'it' was. Now what I'm with isn't 'it', and what's 'it' sounds weird and scary to me. It'll happen to you!
- Made of Iron: Subverted when the doctor informs Homer that his cannonball-to-the-gut sideshow act is killing him.
- Mondegreen: In-Universe example, when Homer buys a Rastafarian hat and shows it off to his kids, Bart protests that he can't wear that hat, Homer says he's been "safarian" since before his kids were born.
- Rhetorical Request Blunder: After the veterinarian warns Homer that he'll die from taking another cannonball, Homer dismisses him.
- Rule-Abiding Rebel: This episode mocks Generation-X'ers for thinking they're cool when in fact they're just insecure and cynical en masse, to the point that they're not even sure if they're really being sarcastic.
- Self-Serving Memory: Homer thinks back to his teenage years as his Glory Days, while the actual flashbacks show him as an unpopular dork who was just too much of a doofus to realise it. The highpoint of his high school years was being an unwanted spectator to someone else's Glory Days, this being the Dazed And Confused parody mentioned below. The only real camaraderie he had was with Barney.
- The "Second-Base Mobile" scene, which is a parody of Dazed and Confused.
- Homers failed attempt at blending in at the music festival includes doing the iconic "Keep On Truckin'" walk created by counter-culture cartoonist Robert Crumb.
- Special Guest: The Smashing Pumpkins, Cypress Hill, Peter Frampton, and Sonic Youth all appear as themselves.
- Stop Motion Lighting: A flashback shows teenagers partying to a strobe light as young Homer watches from a distance. With each flicker, Homer is standing a little closer. When he's rejected, the next flicker has him immediately back where he started, parodying a similar scene from Dazed and Confused.
- The Stoner: Apparently Cypress Hill got so high they ordered a London Symphony Orchestra.
- Makes it more funny in that Cypress Hill uses the orchestra as it that sounds like something they would do when high. It was originally for Peter Frampton, who was on stage at the time.
- Undercover Cop Reveal: Inverted. Homer's attempt at looking cool in Lollapalooza (wearing a Rastacap, a button that reads "Too Cool For This Planet", and talking in old slang) makes the Grunge-rocker teens assume that he's a "narc" and kick him out.
- Waxing Lyrical: Homer laments the loss of the freedom he had in his youth, saying "I used to rock and roll all night and party ev-e-ry day. Then it was every other day. Now I'm lucky if I can find one night a month in which to get funky."
- Who's on First?: When Homer first meets Billy Corgan.
Billy: Billy Corgan, Smashing Pumpkins.
Homer: Homer Simpson, smiling politely.