Quotes / Hilarious in Hindsight

"Comedy can be a dangerous business. It's hard to make the world look ridiculous when it's always finding new ways to make itself look ridiculous."

"At one point in an early scene, Slater sarcastically sneers “Nice job, Terminator 3!” which when taken out of context is some real Nostradamus movie criticism, pre-dating its release by well over a decade. Maybe later there's a line where Lisa comments on the hygiene of a passing nerd with a Kevin Smith stinks!”, or Screech pulls a face and remarks The Hobbit films take all of the worst, most over-indulgent parts of Peter Jackson's output and stretch them across three far too long, atom-thin piles of badly-rendered, unevenly toned, cinematic faeces,” which is a strange non sequitur, even for him."
—Stuart Millard on Saved by the Bell ("Boss Lady"), So Excited, So Scared

"The Mary Tailor-Made Show" must be part of The Da Vinci Code, because you have a man saying "Hey, let's say I make a story for tonight's news about a woman having eight babies?" How many prophecies have you printed that you are not telling the world about?"
MAD reader

"After seeing that Barbie Horse Adventures was on the list, and recalling this old strip, we really had no choice."

"Space Megaforce! Presented by Toho."
Space Megaforce (1992, four years before Touhou)

"Hey, do you remember back in one of my E3 videos, I made a very hilarious joke in which I pretended to mistake the Dead Space 3 trailer for a new Lost Planet? How strangely prophetic that very hilarious joke now seems!"

David: Lois has decided she’s going to keep herself in perfect health with an epic truckload of Vitamin C every day, all generated by creating her own orange juice, “for exercise,” because pills aren’t “natural.” All while smoking cigarettes. Lois Lane: Hipster Extraordinaire.
Chris: Ace reporter for the Portland Daily Planet.
David: “Yo, Clark, want a PBR?”
David Uzumeri and Chris Sims on on Superman II

You also get some unintentionally hilarious moments. Take for example when Bo walks out of his mandatory anger management course and waiting in the lobby is a stressed out Mel Gibson with stacks of journals documenting his “feelings”. That may have been funny at the time when Mel only had a crazy on screen persona, but now when we have heard his ramblings on race, religion, and sex? Comedy gold my friends.
Miles Antwiler on Paparazzi (2004)

Unfortunately, it was supposed to be just a self-contained joke, but current events are making it more and more relevant. Which is not normally how jokes work.
John Oliver to Stephen Colbert on one of his jokes