There is never any value or artistic merit assigned to anything, except for one scene wherein Aech and Parzival have a pissing contest regarding the merits of Ladyhawke, which Parzival considers "canon" (i.e. sacred to Halliday) and Aech does not. There is no such thing as layers of enjoyment, explorations of what made The Shining scary or why Ladyhawke was enjoyable besides that Halliday said so. The characters collect the media of Halliday’s childhood like Pokémon, memorizing his favorite movies and becoming masters at his favorite games, but because of a game of one-upmanship, not because they enjoy them.
Instead, what we get is Halliday's contest for control of his virtual reality world, which rewards the player not for intellectually or emotionally engaging with the media they consume, but instead rote memorization and being mechanically good at video games. A computer could more easily win the contest because the two most important skills -- spitting out memorized lines from movies and playing '80s video games the bestest -- require no critical brain to do so. It's not about the depth of a player's knowledge base or the encouragement of critical thinking (itself the very enemy of nostalgia!), it's about the amount of references they get.
The one integral thing that Spielberg understands is that all of these pop culture references don’t really matter unless they directly relate to what the character is going through. Instead of a series of rewards for slavish rote memorization of movies like War Games, Spielberg’s vision played up the challenges by relating mistakes made throughout Halliday’s life. Memorizing lines from Monty Python and the Holy Grail is replaced with solving puzzles directly relating to Halliday’s own regrets. The film version doesn’t add any dimension to Wade or Halliday’s relationship to the media they’re obsessed with, but at least it understands that it’s hard to stay emotionally engaged in a narrative where the pop culture references have no connection to what’s going on with the characters. So, they fade to the background of reference for reference’s sake, rather than becoming the focus. The film gets its selling points, but still has no thoughts on our relationship to the media we consume.
Spielberg, of course, obliges the audience’s apparently unquenchable thirst for nostalgia, and at times his own (the inclusion of The Shining, for instance, feels quite gratuitous). And there is a place for that -- there is evidence that nostalgia in moderation can actually be good for mental health.
But it needs to be balanced, and big production companies commodifying their own properties to hit those happy buttons cheapens all parties involved. The inclusion of the Iron Giant (and his later death with a thumbs up, a la Terminator 2) as a war machine isn’t a crime, but it does show that the filmmakers don’t really care all that much about the media they are professing to adore, and of their audience, they expect the same.