Trivia / The Good Shepherd

• Development Hell: The Good Shepherd took 14 years of torturous pre-production to reach the screen.
  • The movie grew out of an attempt by screenwriter Eric Roth to adapt Norman Mailer's novel Harlot's Ghost, a similar dramatization of the CIA's early years. Although he had Mailer's blessing, Roth eventually decided that the novel was too difficult to translate to film and scrapped it, keeping only a handful of its broad story elements in his finished script.
  • Francis Ford Coppola was initially attached to direct in 1994, but he disliked Mailer's novel and Roth's early script because he didn't find the characters believable. Philip Kaufman took over from Coppola, but failed to interest studios in the project without a major star attached beforehand. The Good Shepherd languished in Development Hell for a few years (Jane Rosenthal, the film's co-producer, claimed that studios didn't have any interest in a big-scale spy film until 9/11) until John Frankenheimer became attached in 2002, only for Frankenheimer to die in pre-production. Afterwards, Roth learned that Robert De Niro was developing a similar film, met with him and the two decided to combine their projects.
• Enforced Method Acting: Eddie Redmayne says that he had trouble playing Angelina Jolie's son because they are only eight years apart in age and he found her very attractive. For a scene where Redmayne had to compliment Jolie's appearance, Robert De Niro shot hundreds of takes to tire Redmayne out because Redmayne couldn't help but be a little flirtatious in his line reading.
• Fake Brit: British agent Arch Cummings (based on Kim Philby), is played by American actor Billy Crudup.
• Fake Nationality: Russian defector Valentin Mironov (later revealed to be Fake Defector Yuri Modin) is played by English actor John Sessions.
• Underage Casting: Because the film takes place across decades, Matt Damon and Angelina Jolie are only 12 and eight years older, respectively, than Eddie Redmayne, who plays their son. The aging make-up was nowhere near convincing enough to hide this.
• What Could Have Been:
  • Along with Coppola, Frankenheimer, and Kaufman, Wayne Wang was also considered to direct at one point.
  • Leonardo DiCaprio was considered for Edward Wilson.