--STORY RELATED--
This achievement is obtained on your 3rd run-through of the Drive-In Theater.
You will have to match certain things inside the Projector Room to what the manuscript page says:-
It was late at night - change the time to 2am.
It was almost the end of summer - change the calendar to August.
There was a Film Noir poster in view - flip the movie poster to the left of the Arcade Machine
The Red Fire Extinguisher was illuminated - turn the Lamp in the other room to face the Fire Extinguisher in the corner
Alice's film was in the Projector - take the film from the rack in the room with the Lamp and put it in the Projector at the front of the other room.
Once you've done these steps, it will trigger a cutscene and the achievement.