When the town becomes enamored with a Richard Branson-style millionaire who goes on crazy adventures and loves everyone, Mr. Burns realizes no one in Springfield likes, much less loves, him (save for Smithers, but Mr. Burns doesn't know or even care that his assistant has a crush on him) and enlists Homer's help in changing that -- which leads them to Scotland to find the Loch Ness Monster.
This was the last episode to be animated overseas by [[Creator/SunwooEntertainment Anivision]] and is often cited as one of '''''many''''' instances of the show JumpingTheShark (or, rather, the Loch Ness Monster) due to Mr. Burns acting out of character (why ''would'' Mr. Burns give a damn about everyone liking him when many past episodes establish that he values money over human life?) and the near-''WesternAnimation/FamilyGuy'' style jokes (both sexual and non-sexual) that pushed the show's content rating to a TV-14.
!!This episode provides examples of:
* FanDisservice: Homer wears a kilt the [[GoingCommando traditional]] way...much to the displeasure of the bystanders.
* HaveAGayOldTime: Mr. Burns' story of his first gay experience leads to AccidentalInnuendo because he doesn't understand that gay doesn't mean happy anymore (unless it's for literary/ironic purposes). For instance, he recalls his father taking him to a picnic when he was a child, saying "That was a gay old time. I ate my share of wieners that day!"
* LetsGetDangerous: Mr. Burns towards the Monster of Loch Ness. He rolls up his sleeves and catches it off screen.
* MercyKill: PlayedForLaughs. Bart insists Homer to do so, that he doesn't need to participate the family shopping trip.
* NoCelebritiesWereHarmed: Jerry Rude is a clear parody of Howard Stern (and is voiced by former ''SaturdayNightLive'' cast member Michael [=McKean=], who actually played Howard Stern in a couple of sketches).
* NoodleIncident: Mr. Burns capture of the Loch Ness Monster. It involved him somehow being swallowed and passed through the monster's body.
* OutOfCharacterMoment: Why ''would'' Burns care what other people think of him?
* SeriesContinuityError: In "I Love Lisa," Groundskeeper Willie says his "old man" (father) was hung for stealing a pig, but this episode shows that his father is still alive (unless his biological father was a twin or his father somehow survived getting hanged).