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* Martin Scorsese was unaware of the original when he read the script in late 2003. [citation needed]
* Scorsese and the producers wanted to shoot the film on location in Boston where the story is set. But due to economics and politics, the production chose New York City to double for Boston due to a 15% tax incentive. Six weeks were reserved for Boston with the first half in June and the second half in August. Most of the film's exterior shots are filmed in and around Boston.
* Leonardo DiCaprio was cast in the title role in The Good Shepherd, but he dropped out to play Billy Costigan in this movie. Coincidentally, his co-star Matt Damon took his intended role in that film.
* Jack Nicholson signed on to play Frank Costello because in the past ten years he had only done comedies, and he wanted to play a villain again. He has mentioned that he considers his character of Costello to be the ultimate incarnation of evil. [citation needed]
* Both Matt Damon and Mark Wahlberg returned to their hometown of Boston, Massachusetts in this film. Wahlberg's schedule was moved to the beginning of principal photography so he would have time in his schedule for another film, as was Alec Baldwin's.
* Some of the stunts were performed and filmed in the old Fore River Shipyard just south of Boston. This location may have been chosen for the sightlines in the background so the Boston skyline would be true.
* Robert De Niro was offered, but declined, the role of Frank Costello.
* The Dropkick Murphys cover of Woody Guthrie's "I'm Shipping Up to Boston" from their latest abum The Warrior's Code is in the soundtrack and trailer. The Dropkick Murphys are from Boston.
* Also in the trailer and in the film is the Pink Floyd song "Comfortably Numb", as performed by Van Morrison and The Band during the 1990 staging of The Wall in Berlin.
* Jack Nicholson refused to wear a Boston Red Sox hat during filming and instead wore his New York Yankees hat.
* The term 'the faithful departed' is a reference in Roman Catholicism to the belief that baptised souls who have not atoned for their sins will be unable to attain to grace without prayer and the sacrifice of the Mass. Without these the departed are believed to reside in Purgatory.
* Whether on purpose or by coincidence, Frank Costello shares his name with real life New York mobster Frank Costello.
* The character of Frank Costello was largely based on real life Irish Boston mobster James J. Bulger.

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