Spoilers ahead: for the puzzle and the movies/games
This page reveals all categories and answers for this puzzle. It also discusses plot details, story endings, and other spoilers for some of the movies/games shown.
easy
Starring Julia Roberts
Pretty Woman · My Best Friend's Wedding · Notting Hill · Erin Brockovich
medium
Directed by Wes Anderson
Rushmore · The Royal Tenenbaums · The Grand Budapest Hotel · Asteroid City
All four films were directed by Wes Anderson. Note: cinematographer Robert Yeoman shot all four films (as he does on virtually all of Anderson's live-action features), so this overlap is inherent to any Anderson selection rather than an independent alternate solution.
hard
Twist ending that recontextualizes the entire film
The Sixth Sense · The Prestige · Get Out · The Game
Each film is defined by a late-breaking revelation that retroactively changes the meaning of everything before it: Malcolm Crowe is dead all along (The Sixth Sense), the twin-swap magic trick (The Prestige), the Coagula brain-transplant conspiracy (Get Out), and the entire ordeal being a staged theater production (The Game).
tricky
Title contains an animal
The Silence of the Lambs · The Deer Hunter · Birdman · Crouching Tiger, Hidden Dragon
Each title contains an animal name: LAMBS, DEER, BIRDMAN, TIGER, DRAGON. The connection is the wordplay, not any thematic link between the films. Crouching Tiger Hidden Dragon counts twice as a bonus trap.