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:

* ComicallyMissingThePoint: 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.
* GilliganCut: {{Lampshaded}} by Marge tells the businessman she won't be bending her to his sexual will.
-->"Wait! How did I get in your bedroom."
* GoryDiscretionShot: 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.
* GettingCrapPastTheRadar: Homer's predecessor as account executive said he could be his father assuming his mother was a secretary.
** And see NotWhatItLooksLike below.
* HypocriticalHumor: Bart tries sounding out the word "patience."
-->'''Lisa:''' Patience! PATIENCE! Go on with it!
* INeedToGoIronMyDog: "I have surgery in the morning." "Yeah, and I'm the one having the surgery."
* InevitableWaterfall: During the rafting trip.
* NewJobEpisode: Homer becomes an account executive.
* NoodleIncident: Homer hiring Crappy the Clunk as an unauthorized Krusty look-alike for Lisa's first Communion.
* NotWhatItLooksLike: Subverted.
-->'''Luann:''' It's not what you think!
-->'''Kirk, wearing BDSM gear:''' It's much weirder.
* OfficeGolf: Homer plays this game with goldfish.
* SadTimesMontage: Homer gets one for his "meaningless" life as an account executive.
* ShoutOut: The title is a reference to the novel, ''The Man in the Gray Flannel Suit''.
** Krusty's roll-up dickey is set to [[ThisIsSpinalTap eleven]].
** Homer eats steak with the mayor at the [[Disney/TheLionKing Loin King]].
** Lisa's toy bunny is [[ComicStrip/LifeInHell Bongo]].
* TheSoulless: Accountants, according to the businessman.
* TwoTimerDate: Homer tries to be with his family and a group of nuclear regulators on a raft trip.
* WhoWouldBeStupidEnough[=/=]InadvertentEntranceCue:
-->'''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".