Eccentric documentary filmmaker Declan Desmond offers an inside look at his work chronicling some of Springfield's finest for his documentary. Titled Growing Up Springfield, his film follows the lives of several Springfield residents, returning to them after eight-year intervals to examine how their lives have changed. Clips from the film show a young Homer dreaming of growing up to live in a mansion, have a pinball machine with "infinity quarters," and eight pairs of peanut-butter-and-jelly pajamas. Sixteen years later, Homer is working as a manure salesman, infomercial question-asker, and open-casket caricaturist, but dreaming of being a rock star. In an interview with him and Marge, he says they plan to have no children. After the next eight-year interval, Homer has given up on his dreams of fame and fortune to support his growing family. However, when Declan Desmond returns in the present day, he discovers that Homer has become extraordinarily wealthy, and the family is living in a mansion.
Homer explains that his newfound wealth is due to an invention called the condiment pen, which dispenses condiments in the same manner as a writing pen dispenses ink. Declan interviews Marge about her family's unexpected success, but she is unable to explain why the mansion's medicine cabinet is filled with "old man ointments." Suddenly, Mr. Burns bursts into the house, demanding to know what the Simpsons are doing in his summer home.
Homer confesses that his story of wealth and success was a lie. Declan begins to follow him around, wanting to find out why Homer felt the need to lie. When he finally gets Homer on camera, Homer explains that he wanted to feel like a success instead of "the guy who makes everyone else look good." Marge tells Declan off for hurting Homer's feelings and orders him to stay away. Declan suddenly begins to feel sorry for Homer. When he realizes that Moe is envious of Homer's life, Declan is inspired to re-edit the film. Declan puts together footage of Homer's friends and family talking about what a good friend, husband and father he is. Homer sees the new movie and realizes that he is successful after all.