The Rover Hendrix joke (where the veterinarian, when Homer sarcastically asks if he has any more messages for Jimmi Hendrix, tells him to tell Hendrix to pick up his puppy, which is a dog with a blue bandana lying in a sixties decorated bed) was criticized, for some unknown reason, as being one of the worst Simpsons jokes in history. At the time this episode aired Jimmi Hendrix was dead for 26 years as he had passed away in 1970.
Despite Mr. Burns' complete lack of knowledge of the modern world and technology, he somehow knows what Ticketmaster is (although he implies that he knew about it because he had been personally involved with Ticketmaster by purchasing it).
The song the Smashing Pumpkins play Is "Zero."
The song that plays on K-FSL "Fossil 103" when Homer drives the kids to school is "Shinin' On" by Grand Funk Railroad. In another scene where Homer drives the kids, the radio plays "Mississippi Queen" by Mountain.
The song that plays during Homer's flashback to 1974 is "Frankenstein" by Edgar Winter Group.
This is the first episode to feature as part of the episode's beginning something happening to Otto/the school bus that forced various families to enter a carpool to compensate that leads directly to the main events of the episode. This would later be repeated in The Mook, the Chef, the Wife and Her Homer, where Otto got suspended with salary for inflicting corporal punishment on Bart.
When Homer explained that the Us Festival was a music festival organized by Steve Wozniak, the co-founder of Apple Computers, the record store clerk reacted with unfamiliarity to Apple. At the time episode was made, Apple Computers was potentially going to undergo bankruptcy before Steve Jobs returned to operate it. Ironically, however, in the years since then Apple Computers has once again rose to prominence, making the record store clerk's confusion an unintentionally outdated moment.
Courtney Love was supposed to appear in this episode; however Sonic Youth said they would not appear if she did. Some of her lines were re-written for Smashing Pumpkins frontman Billy Corgan.
Homer's first cannonball stunt on the Hullapalooza tour is a near frame-by-frame replica of footage of Frank "Cannonball" Richards, a vaudevillian of the 1930s, performing the same stunt.
During Peter Frampton's concert, Mr. Burns mentions that Smithers used to laugh at his decision to buy ticketmaster, as "no one would pay a 100% service charge."
The scene where young Homer approaches the guys at the van is inspired by the 1993 film Dazed and Confused. One of the guys resembles Matthew McConaughey's character Wooderson, while another resembles Rory Cochrane's character, Ron Slater.
"Homerpalooza" is a parody of Lollapalooza, an annual rock festival.
Otto Mann's talking shoes in Otto's hallucination spoke an opening line from Prince's 1999.
When Homer is lamenting how out-of-touch he is, for a frame the mirror reflection of the top of his head is not colored in.
At Hullapalooza, One of the audience members has orange peace signs on their pants. One of the holes in a peace sign repeatedly is filled in.
Lisa eats bacon for breakfast, 19 episodes after she announced of being a vegetarian.
It might have been made of tofu.
After the first time Homer gets struck by a cannonball, the ball disappears in the next shot.
After dodging the cannonball, Homer is wearing a helmet, goggles, blue shorts and tennis shoes, but when he steps off the stage, the helmet and goggles disappear and he is wearing his blue flannel pants and his gray shoes.
At the end when the Pumpkins walk away, during the wide shot they are completely different people.