The Simpsons host a party to promote Krusty's new Vodka product. Homer gets a promotion to an account executive. Lisa teaches Bart how to enjoy reading.
- Comically Missing the Point: When Homer was offered the position of account executive, his predecessor said he'd lose his soul. Homer was glad at the prospect of no longer having to go to church. Later, when Homer asked his predecessor how to get ready for a meeting with the Mayor, he was given an extra glass of Bourbon. He enjoyed the drink but missed the hint.
- Gilligan Cut: Lampshaded by Marge tells the businessman she won't be bending her to his sexual will.
"Wait! How did I get in your bedroom."
- Gory Discretion Shot: Homer rides by Mr. Burns on a lawn mower, and a bunch of blood spatters bystanders. Cut back to Mr. Burns, who grabs his leg.
- Getting Crap Past the Radar: Homer's predecessor as account executive said he could be his father assuming his mother was a secretary.
- Hypocritical Humor: Bart tries sounding out the word "patience."
Lisa: Patience! PATIENCE! Go on with it!
- I Need to Go Iron My Dog: "I have surgery in the morning." "Yeah, and I'm the one having the surgery."
- Inevitable Waterfall: During the rafting trip.
- New Job Episode: Homer becomes an account executive.
- Noodle Incident: Homer hiring Crappy the Clunk as an unauthorized Krusty look-alike for Lisa's first Communion.
- Not What It Looks Like: Subverted.
Luann: It's not what you think!
Kirk, wearing BDSM gear: It's much weirder.
- Office Golf: Homer plays this game with goldfish.
- Sad Times Montage: Homer gets one for his "meaningless" life as an account executive.
- Shout-Out: The title is a reference to the novel, The Man in the Gray Flannel Suit.
- Krusty's roll-up dickey is set to eleven.
- Homer eats steak with the mayor at the Loin King.
- Lisa's toy bunny is Bongo.
- The Soulless: Accountants, according to the businessman.
- Who Would Be Stupid Enough/Inadvertent Entrance Cue:
Lenny: Boy, everyone from the Nuclear Plant is here, except the bosses of course.
Carl Carlson: Yeah, even Homer's not dumb enough to invite—
Mr. Burns: (Holding a party invitation.) Ooh, so this is the famous "party".