Springfield resident Chip Davis (a man who never appeared on the show yet apparently greatly impacted everyone in some way) dies, prompting some of the people he knew to reflect on their own lives and choices. Homer regrets selling his Apple stock for a bowling ball, and becomes increasingly irritated that Mr. Burns is gloating about buying Homer's stock with successful results.
Marge worries that her listening to Kiss albums while pregnant with Bart made him what he is today as she watches him acting out during Chip Davis' funeral with Milhouse, including removing the church's pew kneelers, hurting everyone's knees when everyone kneels to pray, stealing the collection plates and using them as swords, and stealing Reverend Lovejoy's gown, mocking him.
Mr. Burns regrets breaking up with a French woman Lila who became a Buddhist monk after rejecting his engagement proposal due to his selfishness. He later finds her in a Buddhist temple, and the two reunite. He then goes to the bathroom to freshen up. But when he returns, he finds her dead in bed after taking too long to prepare. He tries resuscitating her, but his "breath of life" ends up disintegrating her body. Smithers then encourages Mr. Burns to honor the one wish she had for him: be selfless for at least five minutes. Mr. Burns then sets out to volunteer at the soup kitchen, where he ends up staying longer than five minutes.
Kent Brockman regrets not taking a position as a cable news anchorman when he had the chance when he was younger. He later goes to New York City looking for a job. After reviewing his choices, he heads to Fox News, where one anchor encourages him to blame the Democrats for what happens in the news. After realizing the pettiness of the news station, Kent decides to return home.
Later, Bart decides to fly after making a balloon ride out of a laundry basket and hundreds of balloons. However, he begins to regret his decision after ascending too high into the air. Kent then sees this and broadcasts it on the news in hopes of regaining his drive for local news. Homer then uses his bowling ball as a way of weighing down Bart's balloon ride by shooting it out of a cannon which lands on the basket and brings Bart back to the ground. Everyone celebrates Bart's rescue while ignoring Lisa's success at an academics competition. Homer then begins to appreciate his bowling ball again, but then it explodes after a police sniper accidentally shoots it.
Before the credits roll, a tribute to Marcia Wallace is shown, with Mrs. Krabappel in her classroom.