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.

Tropes:

• Bait-and-Switch Comment: While at the party, Mr. Burns requests a song by Prince, by which he means a Prussian Kaiser.
• 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.
• Didn't Think This Through: Krusty's vodka is hard to sell because it's not easy to convince adults to buy vodka bottles with clown faces.
• Gilligan Cut: Lampshaded by Marge tells the businessman she won't be bending her to his sexual will. The discussion constantly changes places.
  "Wait! How did I get in your bedroom."
• Gory Discretion Shot: Homer rides by Mr. Smithers on a lawn mower, and a bunch of blood spatters bystanders. Cut back to Mr. Smithers, who grabs his leg.
• 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.
• Literary Allusion Title: The title is a reference to the novel, The Man in the Gray Flannel Suit.
• 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.
• Seduction-Proof Marriage: Robert Marlowe is so smooth he manages to get Marge out of his living room, into his bedroom, and then into his bathroom (with him naked in the shower) without her noticing. However, Marge declares she's Happily Married and turns the tables by sending them back to the living room before he realizes. A surprised Marlowe notes this is the first time someone's managed to do this.
• Shout-Out:
  • 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 scene where Homer drunkenly runs over Smithers' foot on a riding mower is taken shot-for-shot from Mad Men (doubles as an Actor Allusion to the episode's guest-star, John Slattery).
• The Soulless: Accountants, according to the businessman.
• Two-Timer Date: Homer tries to be with his family and a group of nuclear regulators on a raft trip.
• Who Would Be Stupid Enough?:
  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".