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"The Man in the Blue Flannel Pants" is the seventh episode of Season 23, originally was going to be the first episode of that season.
Homer is promoted to account executive and has an ad professional to guide him through the process. However, Homer's newfound lease on life comes at a cost. In the meantime, Bart starts classic works.
Krusty is about to perform a stunt when two of his agents mention that there is trouble with Krusty's newest product, Absolute Krusty. To make it popular, the agents insist that Krusty hold a tastemaker party at the home of a Springfield trendsetter.
At 742 Evergreen Terrace, Homer, Marge and other adults are having a fantastic time until Mr. Burns comes over and frightens the guests. Homer ends up saving the party by singing karaoke with Burns. As a result of this matter, Homer receives a hefty promotion to account manager.
On his first day of his new job, Homer is taught how to live the life of an accountant manager by Robert Marlowe, the person whom Homer is replacing. Homer soon develops a depressed, drinking attitude and complains about how his new job is meaningless.
It soon becomes apparent to Marge that Homer is spending less time with the family because he now works longer. Marge insists that the family go on a vacation to help Homer realize that family comes first.
Homer is keen to the idea until he learns that Burns wants to go rafting with some of the other businessmen, a trip that Marge wanted Homer to join along with her and the kids. On the trip, Homer balances the two out until Marge takes notice and gets upset. Homer tries to explain his story, but the two rafts are almost at a steep waterfall. Homer can only save one raft, and soon saves the raft that Marge and the kids are on. Marlowe arrives and saves the raft that Burns and the businessmen are on.
Later that night, Homer tells Marge that he was demoted back to his old job. Fireworks are soon seen, but they were from a fire at the Power Plant.
In the subplot, Lisa attempts to introduce Bart to classic novels. Bart struggles at first, but soon catches on and is soon forced to read Little Women to the school bullies.