Declan Desmond makes a documentary highlighting the progress in the lives of several Springfieldians.

!! Tropes:
* BaitAndSwitch: As a mall photographer, Marge is shooting a picture for what appears to be a young Captain [=McAllister=], but when she plays disco music, he suddenly transforms into Disco Stu.
* BigNo: Smithers shouts several of these as a result of being tied up inside a grandfather clock and forced to hear the loud chimes.
* BrickJoke: After interviewing Lenny at age eight, Desmond declared that he was too boring to continue the documentary process on him. Later on, Desmond attempts to confront Homer at his house (since he'd been dodging him about his attempt at appearing wealthy backfired), Lenny shows up to try and be interviewed again. Doesn't take long for Desmond's blatant refusal to talk to him for Lenny to get the hint and leave.
* DownerEnding: For Elanor: she got burnt out from her multiple jobs, fell off the wagon, and decided to buy multiple cats, eventually becoming Crazy Cat Lady.
* EveryoneWentToSchoolTogether: Many of Springfield's adult characters are seen at elementary school together.
* FunnyBackgroundEvent: While Homer sings his song to Desmond, a young Carl briefly appears behind him in Frink's time machine.
* GilliganCut: When Desmond asks Homer and Marge if they're considering having kids, Homer said he wouldn't be caught with a couple of rugrats. The next scene is eight years later with Bart and Lisa as babies.
-->'''Homer''': [[LampshadeHanging You'd better not put this after the scene where I said I wouldn't have any kids]]. ''[[LampshadeHanging That]]'' [[LampshadeHanging would be a devastating edit]].
* MockMillionaire: Homer pretended to be wealthy to impress Desmond, but Mr. Burns unexpectedly showed up and ended the hoax.
* NeverTheSelvesShallMeet: Professor Frink tried to tell his past self not to pursue a scientific career. He was ran over in the past, preventing him from getting young Frink's attention.
* OriginsEpisode: We see the origins of the CrazyCatLady, like her real name Eleanor Abernathy.
** Similarly, we learn how Disco Stu came to be.
* OrphanedPunchline: "And that's how I got the vending machine contract for the Kremlin."
* TheReasonYouSuckSpeech: Two, back to back, happen when Desmond tries to confront Homer at his house: one from Homer about himself, and one from Marge to Desmond.
-->'''Desmond''': Then I just want to know why your husband did what he did.
-->'''Homer''': (from offscreen) I'll tell you why. (walks up to the door) It's been another eight years, and what do I have? Same job, same house, (pulls out "Pat Summerall's 'Smut Yuks'") same dirty joke book. (reads book and deadpanly laughs; tosses book to the side) I just thought for once I could be the cool guy in your movie. But all I am is the guy who makes everyone else look good. (leaves)
-->'''Desmond''': (turns to the camera) Strong words from a dumpy man. (makes "cut off" gesture) And cut.
-->'''Marge''': (fed up; to Desmond) Wait just a cotton-swabbing minute! A good man went to a lot of trouble just to impress you. And I went along with it because I love him to pieces. And you made him look like a fool. Well, I don't want you anywhere near my house! (to the camera) ''Now'' you can cut! (camera does)
* RememberTheNewGuy: Subverted. At first, it seems like the episode had created the character Eleanor Abernathy, but as we learn by the end of the segment, she actually goes by a more well known alias: Crazy Cat Lady.
* RoyaltiesHeir[=/=]InventorOfTheMundane: Homer (falsely) claimed he became wealthy by inventing the condiment pen.
-->'''Homer:''' I got the idea from the regular pen.
* SelfMadeMan: The sort of wealthy man Homer pretended to be.
* SetRightWhatOnceWentWrong: Professor Frink tries going back in time to convince his eight-year old self to abandon the field of science... [[DefiedTrope only to get run over by a couple cars when he attempts to cross the road to get to him]].
* SomethingCompletelyDifferent: This episode feels a tad bit different from your average Simpsons episode. Almost all of this episode focuses on the perspective of Desmond as he shoots and edits his documentary, instead of the "wacky adventures" the Simpsons (and their friends and enemies) go through. Even the opening and ending of the episode were both quite different from your average Simpsons episode in its initial airing.
* WhamShot: The ending portion of the "Elanor Abernathy" segment: Crazy Cat Lady tossing cats at the cameraman. And as if the connection wasn't clear enough, she ''also'' throws her diploma from Yale.
* {{Workaholic}}: Being both a doctor and a lawyer left Eleanor Abernathy feeling burned out at age 32, and so, [[TheAlcoholic she started drinking]] and acquired her first cat.
* YouAreBetterThanYouThinkYouAre: In order to make it up to Homer, Desmond went through ''all'' of ''thousands upon thousands'' of footage he gathered, "''twice''", in order to find ''every instance'' of people talking positively about Homer.