Round 66: Homerpalooza vs. Sideshow Bob’s Last Gleaming

Round 66: 3F21 vs. 3F08.

3F21: “Homerpalooza” (Season 7 / May 19, 1996)
Written by Brent Forrester
Directed by Wes Archer
Showrunners: Bill Oakley & Josh Weinstein

Homer Simpson in a record store

“Styx? I just heard them on the King Biscuit Flower Hour.”

In theory, I should hate this episode. One of my top complaints about the last few years of “The Simpsons” is how violent the show has become, especially towards Homer. The premise of “Homerpalooza” is based on the fact that Homer can take an endless amount of pain and abuse without flinching a muscle. But the way it’s presented and integrated into the story here, it works. (If that sounded familiar, it’s because I stole most of it from Round 9.)

This is an interesting little time-capsule of an episode. Sonic Youth’s “Goo” is now older than Grand Funk’s “Shinin’ On” was in 1996. And while my own musical taste is a little closer to Homer’s than Bart’s, I could relate to both sides of their generational conflict.

  • -“You don’t have to join a freak show just because the opportunity came along.”
    -“You know, Marge, in some ways, you and I are very different people.”
  • -“What religion are you?”
    -“You know… the one with all the well-meaning rules that don’t work out in real life. … Christianity.”
  • How, almost twenty years later, is there still no full version of “Insane in the Brain” by Cypress Hill and the London Symphony Orchestra?

3F08: “Sideshow Bob’s Last Gleaming” (Season 7 / November 26, 1995)
Written by Spike Feresten
Directed by Dominic Polcino
Showrunners: Bill Oakley & Josh Weinstein

Sideshow Bob in a prison bunk bed

It’s always a bummer when two great episodes (from a great season) meet each other this early in the tournament. Both would’ve gone far if they had faced off against lesser episodes at this stage. But what can you do?

Beautiful, dramatic animation, wonderful guest voices by Kelsey Grammer and R. Lee Ermey, a script with a nice mystery, tons of laughs, and plenty of obscure and less obscure movie and pop culture references. This is an all-time great Simpsons episode.

The winner: 3F08, “Sideshow Bob’s Last Gleaming.”