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

!! Tropes:
* BaitAndSwitch
** One of the children followed by the documentary becomes a successful laywer and doctor, but then loses her job and becomes the CrazyCatLady.
** 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.
* 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.
* FutureLoser: What the Crazy Cat Lady ends up being.
* GilliganCut: When Declan 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 Declan but Mr. Burns unexpectedly showed up and ended the hoax.
* NeverTheSelvesShallMeet: Prof. 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.
* OrphanedPunchline: "and that's how I got the vending machine contract for the Kremlin."
* 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.
* SomethingCompletelyDifferent: This episode feels a tad bit different from your average Simpsons episode. Almost all of this episode focuses on the perspective of Declan 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.