What are the oldest and youngest works referenced by James Halliday in Ready Player One?

Question

In Ready Player One, James Halliday has riddled the Oasis in general and the quest specifically with references to things he enjoyed in his youth in the '80s. Music, such as 2112. Films, such as War Games. Games, such as Joust.

What is the oldest piece of real life, 20th century pop culture referenced by James Halliday? And what is the most recent one (20th or possibly 21st century)?

This can be a part of a challenge, or something else created by James Halliday and inserted in the Oasis, that reflects a person, group, organisation, work, object, or anything else that exists or has existed in real life.
This assumes more or less that the timeline as presented in Ready Player One is equal to the real world timeline up until present day (technically until the date of publication).

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I'm interested primarily in the book. Answers based on the film should mention that they are.

Answer 1

TL;DR:

• Earliest book reference: Tennis for Two, invented by William Higinbotham in 1958
• Earliest movie reference that's certain: Robby the Robot, from 1956 Forbidden Planet and Cyclops from Ray Harryhausen's The 7th Voyage of Sinbad (1958)
• Earliest movie reference that isn't by Halliday: Kira is referred to as "rosebud", a reference to 1941 Citizen Kane
• Earliest disputable movie reference: 1933 original King Kong or 1948 Marvin the Martian.
• Latest book reference: 2008 Indiana Jones and the Kingdom of the Crystal Skull
• Latest disputable book reference: 2011 Ready Player One audiobook, narrated by Will Wheaton
• Latest movie reference: characters from 2016 Overwatch videogame

Earliest References

Book

The museum’s bottom level, located in the planet core, was a spherical room containing a shrine to the very first videogame, Tennis for Two, invented by William Higinbotham in 1958. The game ran on an ancient analog computer and was played on a tiny oscilloscope screen about five inches in diameter. Next to it was a replica of an ancient PDP-1 computer running a copy of Spacewar!, the second videogame ever made, created by a bunch of students at MIT in 1962.

Movie

• Child Halliday's room recreation features Robby the Robot, from 1956 Forbidden Planet
• During opening sequence, DenOfGeek's commenter David Thiel spotted the Cyclops from Ray Harryhausen's The 7th Voyage of Sinbad (1958).

Disputable

• One avatar is Marvin the Martian who first appeared in 1948. But it existed till ~2000.
• When Nolan Sorrento first approaches I-R0k, he steps out of a crashed martian ship from the 1953 War of the Worlds (from the same DenOfGeeks article). However, this probably isn't a mention by Halliday so may not count.
• Depending on how you squint, you can count the movie's King Kong - it could be counted as a reference to 1933 original King Kong; however visually it most resembles 2005 remake one.
• There was also a quote by one of the movie characters who was quoting 1946 It’s a Wonderful Life: “No man is a failure who has friends.”
• In the movie (but not the book), Kira is referred to as "rosebud", a reference to 1941 Citizen Kane. But, that's NOT Halliday doing so.

Any Pop-culture Event

Depending on whether you count it as "works", we also have a famous event 1922 that was featured in many popular culture works and culture overall:

During our World History lesson that morning, Mr. Avenovich loaded up a stand-alone simulation so that our class could witness the discovery of King Tut’s tomb by archaeologists in Egypt in AD 1922. (The day before, we’d visited the same spot in 1334 BC and had seen Tutankhamen’s empire in all its glory.)

Latest References

Book

Just for completeness, I'll have to steal JohnP's answer of 2008 Indiana Jones and the Kingdom of the Crystal Skull; in my defense, his answer borrowed that factoid from someone else, I assume a commenter.

Disputable

The latest work was (indirectly kinda) 2011 audiobook of Ready Player One itself, narrated by Will Wheaton.

Movie

As per DenOfGeek article again, the final battle avatars included characters from 2016 Overwatch videogame

From this article, here's the two superimposed images:

Disputable

(again from DenOfGeeks article)

During the final third of the film, we discover the fate of the OASIS depends on your dexterity with an Atari 2600. If you pick the wrong game, into the ice you go, which feels like it could be a nod to the “banishment” seen in The Dark Knight Rises (2012), as Spielberg is a vocal admirer of Christopher Nolan and those Batman movies

As this is earlier than Overwatch, doesn't really matter, but still too cool to avoid mentioning.

Answer 2

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.