After Homer wins a storage locker at an auction filled with feather boas and 1950s muscle magazines, Grampa Simpson confronts his past as Springfield's most reviled pro-wrestler, especially when Bart begins following in his footsteps and Mr. Burns reveals that he was — and still is — Grampa's biggest fan (never mind that the "Curse of the Flying Hellfish" episode established that Grampa Simpson and Mr. Burns have hated each other since World War II and Grampa kicked him out of the tontine after Burns tried to drown Bart).
- Card-Carrying Villain: Mr. Burns included himself as an example during the "High to be Loathed" song.
- Dastardly Whiplash: While singing about the perks of being hated, Mr. Burns got somebody's wig to use as a moustache.
- Department of Redundancy Department: "Oh, my gay dad is gay for gays."
- Gilligan Cut: Homer angrily tries to call off Bart and Abe wrestling together. It doesn't work.Homer: Why must everything I forbid always happen?
- Gorgeous George: Grandpa's wrestling persona, Gorgeous Godfrey.You're the luckiest people in the world. You get to look at me.
- HeelFace Turn: Grandpa changes from Gorgeous Godfrey to Honest Abe mid-match.
- Little Brother Is Watching: Grandpa gets second thoughts about playing the heel after seeing Bart imitate his antics.
- Mistaken for Gay: When the Simpsons first find that Grampa's storage locker is filled with feather boas, wigs, and old muscle magazines from the 1950s, they assume that he's a closet homosexual who's angry all the time because he lived during a time when expressing homosexuality meant you were insane or sexually deviant.
- Pro Wrestling Episode
- Shout-Out: The list of villains Mr. Burns mentioned in his song includes: Skeletor, Megatron, Donkey Kong, Chucky, Eric Cartman, Vader.
- Oddly, the design used for Megatron is based on a random figure◊ that wasn't hadn't been on shelves for 4 years by the time the episode aired, and wasn't featured in any cartoons.
- Take That!: When Mr. Burns was told wrestling is fake, he looked at the camera and said it'd make an idiot out of every wrestling fan.
- Villain Song: It's a high to be loathed.