Noticing that Moe has fallen into a bout of suicidal depression, Homer, Marge, Lenny and Carl take him on an excursion to Capital City and buy him a new suit to lift his spirits. His enthusiasm restored, Moe fixes up his bar in order to attract a better class of customers and brings out a batch of homemade whiskey. Two venture capitalists stop by the bar, sample the drink, and are so impressed that they offer to become Moe's business partners in marketing it. Shortly before the new company's initial public offering, his suit is destroyed when he gets caught in an elevator door. Moe appears at the stock exchange in his ordinary clothes and addresses the traders for the IPO, but he inadvertently scares them so badly that his stock price plummets and the company becomes worthless. Returning to his once-again-squalid bar, he brightens up enough to sweep up the pieces of a broken beer mug and forgets about committing suicide, at least for the time being.
Meanwhile, Grampa watches the children while Homer and Marge are away. An elaborate prank by Bart, Dolph, Jimbo, and Kearney leads to Grampa being injured, and Bart decides to care for him at home in order to avoid getting in trouble. With Grampa hiding in the basement to avoid being found, the two enjoy playing tricks on Homer. Grampa recovers quickly, but fakes a lingering injury in order to make sure that Bart keeps looking after him. Bart eventually discovers the deception and is angry, but the two reconcile after Grampa explains that he liked getting the sort of personal attention that he never could receive at the nursing home.
In order to keep Lisa from finding out about Grampa, Bart sends her to a jazz club where an all-star jam session is taking place. She is shocked to see Bleeding Gums Murphy among the performers, as she knows him to be dead, and discovers that he is actually a hologram. Outraged, she tries to start a boycott of Murphy's record label; shortly afterward, she is surprised to receive a visit from saxophonist Sonny Rollins at home. Rollins explains that holograms are simply the next step in the development of the entertainment industry. Realizing that he too is a hologram sent by the record company, Lisa gives up her boycott and groans resignedly as she watches commercials that feature Diana, Princess of Wales, Tupac Shakur and Mahatma Gandhi.