Pulp Fiction is a must. In fact, they could do Forrest Gump, Pulp Fiction, Shawshank, Ed Wood, and Quiz Show.
They could do an entire episode just about 1999. Like 1939, it was a landmark year for cinema:
The Matrix
Office Space
Fight Club
Eyes Wide Shut
American Beauty
The Sixth Sense
Being John Malkovich
The Green Mile
Boys Don't Cry
Girl, Interrupted
https://en.wikipedia.org/wiki/1999_in_film
Toy Story 1 & 2 definitely. The big Disney Renaissance films.
Scream and the glossy 90s teen slashers.
Edit: I somehow got this confused with CNN's The Movies. I still like the 1999 idea. They should definitely throw in some blockbusters and tentpoles.
Batman
Batman Returns
Superman
Spider-Man
Batman Begins, The Dark Knight and/or the entire Dark Knight Trilogy
MCU
Halloween
Friday the 13th
A Nightmare on Elm Street
The Thing
Escape From New York
The Warriors
Blade Runner
Tron (They could especially talk about the then-groundbreaking special effects)
The Wrath of Khan
Star Wars original trilogy
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