Stories from the set

At the very beginning of the film, Professor Lambeau writes on the blackboard and lowers it; a few frames later the blackboard is raised, and then in a close-up we see it lowered again.

At the construction site, when Will and Chuckie are talking, at the end of the conversation Chuckie is holding a beer in his right hand, and in the next shot in his left.

Here is how Matt Damon and Ben Affleck went looking for a film company: on page 60 of the script they inserted an erotic scene involving Will and Chuckie, and this scene was clearly out of place there, and they began offering the script to major studios. None of the people they spoke with at those studios even mentioned this scene. Only Harvey Weinstein from Miramax mentioned it and asked what this completely out-of-place scene was doing there. Damon and Affleck explained that this was how they determined which studio had read the script and which had not.

In his fifth year at Harvard, Matt Damon studied playwriting. One of the assignments was to write a one-act play; with Ben Affleck's help, it later turned into this film.

A significant portion of Casey's lines were improvised. Matt Damon, Ben Affleck, and director Gus Van Sant later admitted that those lines were much funnier than the ones they had prepared for Casey.

In the scene with Robin Williams (1951-2014) and Matt Damon on the park bench, it seems as if there is no one else nearby. However, Williams was an extremely popular actor, and at one point more than 3,000 people were watching the filming.

The painting seen in the office of Robin Williams's character was painted by Gus Van Sant.

After Robin Williams's death in 2014, the bench where he talked with Matt Damon's character in the film became a place of pilgrimage; people left flowers there and so on.