- This is Ben Affleck's major film directoral debut, and his first screenplay credit since Good Will Hunting.
- It is based on a book of the same name by author Dennis Lehane, who also wrote books-that were-turned-into-movies Mystic River and Shutter Island.
- All of the extras were Boston locals, intentionally cast that way for authenticity.
- Ben Affleck considered starring in the film, instead the lead went to his brother Casey.
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