Dang, awesome list.

Neverwinter Nights 1 Diamond Edition (unfortunately only "available" by purchasing the new version and getting Diamond as an extra) mod Some Distant Shore and cinema masterpiece The Seventh Seal .

Perhaps more of a stretch, Night Call and Collateral

For an outside-the-box pick, how about Noctropolis paired with unfairly maligned cult classic (to me anyway) The Spirit ?

Surely there are parallels to draw between pre-2013 Tomb Raider games and the Indiana Jones movies.

If TV shows are also allowed, Deadly Premonition is clearly inspired by Twin Peaks and The X-Files .

For anyone interested in it, I notice that Deadly Premonition is also on sale for about the next two and a half days; in US the price is listed as $1.24 when I looked now.

Edit: made links to read more neatly

Putting aside a moment that there's a Mad Max game, I dare say Fuel pairs well with Road Warrior in particular, just for the emphasis that gasoline is a dying resource.

Stellaris and Star Trek. Not only they share a myriad of scifi tropes (many of which were established by Star Trek); it is clear the Trek universe was the inspiration for many events and gameplay mechanics.

I don't know. Maybe Theme Hospital and Scrubs, even so Scrubs was just a TV-show.

edit:
removed a "maybe" too many

Hmm . Maybe ?

film: Dagon (2001)
game : Call of Cthulhu: Dark Corners of the Earth

How about some American Western themed pairings:

Red Dead Redemption (game)

with

True Grit (original version) or Unforgiven (movies)

Stray - The Cat from Outer Space

Requiem: Avenging Angel - Legion

Even better: Stray and Flow! Both fallow a regular house cat in a world previously bristling with humans, now overflowing with either mobile fungal creatures or literal water.

I was trying to come up with something for Grim Fandango. Beetlejuice would probably fit best, although I guess you could also make an argument for Corpse Bride. Either way, it has to be Burton.

Oh, and Ben There, Dan That / Time Gentlemen, Please would go very nice I think with Bill & Ted's Excellent Adventure. Comedy, time travel, two goofy best friends as protagonists.

This only makes me wish we had Stray here all the more, as Flow was really great.

Showgunners - The Running Man

Grim Fandango HAS to go with Coco.

I dont know... it's subjective to a degree, of course, but I feel like Coco is too cutesy for Grim Fandango. At least the way I remember Fandango it definitely felt more Burton than Pixar.