Note: The below answers are from the book.
Oldest pop culture reference
Captain Crunch Bosun's Whistle - Mid 1960's - The discovery of the whistle tone is attributed to John Draper (aka Cap'n Crunch) an early phone phreaker/hacker. It is a whistle that emitted a tone of 2600 Hz that enabled free phone calls at the time, which was included in boxes of Cap'n Crunch cereal. There is no more precise date than mid to late 1960's.
Supporting quote (Clue for the second/Jade key, written by Halliday):
One entire cupboard what crammed with boxes of vintage breakfast cereals, most of which had been discontinued before I'd been born. Fruit Loops, Honeycombs, Lucky Charms, Count Chocula, Quisp, Frosted Flakes. And hidden way at the back was a lone box of Cap'n Crunch. Printed clearly on the front of it were the words "Free toy whistle inside!"
The captain conceals the Jade Key
Honorable mention: The planet Chthonia (Created by Halliday), which could go all the way back to Greek Mythos, but possibly also from the Chthonian creatures created by Brian Lumley in the Cthulhu mythos, short story titled "Cement Surroundings", 1969.
Newest pop culture reference:
Indiana Jones and the Crystal Skull movie, release date May 20, 2008.
I devoured each of what Halliday referred to as “The Holy Trilogies”: Star Wars (original and prequel trilogies, in that order), Lord of the Rings, The Matrix, Mad Max, Back to the Future, and Indiana Jones. (Halliday once said that he preferred to pretend the other Indiana Jones films, from Kingdom of the Crystal Skull onward, didn’t exist. I tended to agree.)
Thanks to @Odin1806 for the catch.
Final note: There are older references (Such as Galileo and Shakespeare) that are directly referenced by Halliday, but the OP wanted it limited to 20th/21st century artifacts.