The film chronicles the foundation of the CIA through the life of Edward Wilson (Damon), a fictional spy who participated in its predecessor's activities. Over the course of the film Wilson's dedication to his work is contrasted with his detachment from daily life as he fails at being both a husband and a father.
This film provides examples of:
- Actor Allusion:
- Alec Baldwin (The Hunt for Red October), Michael Gambon (Bullet to Beijing and Midnight in St. Petersburg), William Hurt (Master Spy: The Robert Hanssen Story, a Made-for-TV Movie), and Timothy Hutton (The Falcon and the Snowman, Aldrich Ames: Traitor Within, a Made-for-TV Movie) had all appeared in spy-related movies in the past. As in his previous spy movies, Hutton's character is a traitor, and Hurt's character is not who he seems to be.
- As noted below under No Celebrities Were Harmed, Joe Pesci plays a mobster based partly on Sam Giancana
, who allegedly was involved in the Bay of Pigs Invasion, and whom some conspiracy theorists believe was involved in the plot to kill John F. Kennedy. In JFK, Pesci played David Ferrie, who was involved in the Bay of Pigs invasion, and who was supposedly involved in the plot to assassinate Kennedy.
- Arc Words:General Sullivan: (to Edward) No matter what anyone tells you, there'll be no one you can really trust.
- Artistic License – History: In detail.
- Bodyguard Betrayal: Wilson, essentially the head of the nascent CIA, occasionally meets his Soviet counterpart, codenamed Ulysses. Late in the film, it's revealed that Ulysses' aide is funneling information to the Americans, direct from the source. The aide doesn't kill Ulysses or even cause him any direct harm, but his actions are definitely a betrayal in the general sense.
- Book Safe: One can apparently also conceal documents between the inside of a book cover and its lining without removing any pages at all.
- Boom, Headshot!: Hannah ends up getting executed this way after she's found out (see Obfuscating Disability below).
- Chekhov's Gun: The copy of Ulysses. Yuri Modin's passport is hidden within the cover.
- Churchgoing Villain: Edward Wilson is an Anti-Hero version of this. He is a practicing Christian who has verses from The Bible inscribed on the walls of the CIA. He is also willing to drug, torture, and kill people. He's also a Noble Bigot with a Badge.
- Deadpan Snarker: Ray Brocco.Edward: How do you know you're in the right place?
Ray Brocco: They told me to look for a serious son of a bitch with No Sense of Humor; there can't be two of you. - Defector from Commie Land: Valentin Mironov is a former KGB agent who defects to the United States to assist Edward Wilson's counterintelligence unit in the new CIA against the Soviets. Turns out he's a Double Agent.
- Excrement Statement: In the pre-war segments, there's a Skull and Bones initiation that involved members urinating and defecating on the initiates from an indoor balcony.
- Fake Defector: A long-term example, where a Soviet defector named Valentin Mironov spends years working with Edward Wilson in Wilson's counterintelligence unit. Another Soviet defector later shows up to claim that he's the real Mironov, while the first one is actually Yuri Modin, a KGB agent. They don't believe the second "Mironov" and torture him until he jumps out a window to his death (it doesn't help that he's dosed with LSD at that point). The first "Mironov" offers to take a polygraph test to prove that he is who he says he is, but Wilson refuses. Later, though, Wilson shows up on Mironov's doorstep in the middle of the night and demands that Mironov play his violin. When Mironov agrees and asks why, Wilson replies that he wanted to finally hear something from "Mironov" that was true. Obviously, he figured out that the second "Mironov" was the real deal.
- Honey Trap: Used repeatedly by nearly every woman in the entire movie!
- Long Song, Short Scene: There is an arrangement of "Oh Shenandoah". Of course, we only hear part of it, and in the background behind the dialogue. It is MIA on the soundtrack, and hours of aggressive searching on the internet have turned up fruitless.
- Never Trust a Trailer: They pinned the movie as a deep look into the history of the U.S. Central Intelligence Agency, better known as the CIA, including scenes of supposed espionage underway. Really much of the movie is about the personal life of Edward Wilson’s various affairs with women and his struggling marriage. And he just happened to find a secretive agency that spends most of its time trying to decipher a mysterious video.
- No Historical Figures Were Harmed: Almost all the characters are fictionalized analogues of real people:
- Edward Wilson is James Jesus Angleton & Richard Bissell. His name is also very similar to controversial CIA figure Edwin Wilson.
- Arch Cummings is Kim Philby.
- Bill Sullivan is William J. Donovan.
- Philip Allen is Allen Dulles.
- Joseph Palmi is Sam Giancana & Santo Trafficante Jr.
- Thomas Wilson is James Forrestal.
- Yuri Modin is Anatoliy Golitsyn.
- Richard Hayes is Richard Helms.
- Valentin Mironov is Yuri Nosenko.
- Edward Wilson is James Jesus Angleton
- Not the Fall That Kills You…: Averted with Edward Jr's fiancée Miriam, who is thrown out of a plane in mid-flight and doesn't survive.
- Obfuscating Disability: Hanna Schiller, a German translator working for Edward, is pretending to be deaf since she needed some way to use a recording device without being obvious, so she masks it as a hearing aid. She gets found out when Edward calls to her from behind, and she reacts.
- Sarcastic Title: Edward Wilson, an emotionless robot of a man who built up the CIA, can hardly be called a good shepherd. Even in his private life he ultimately does more harm than good.
- Shout-Out:
- When Edward first appears in the flashback to 1939 at Yale, he's performing (in drag) in a production of H.M.S. Pinafore.
- When Edward takes Laura out dancing on one of their first dates, the band is playing "Blue Skies", and Edward sings part of it to her.
- At a Skull and Bones gathering, Philip and several of the older members of the group perform "There is Nothing Like a Dame".
- Shotgun Wedding: Edward gets Clover pregnant the first time they have sex, which is also the night of the day they meet. Her brother tells him "I know you will do as expected". He does, despite being in love with another woman. He then leaves a week after the wedding for six years to fight in World War II and after returning, becomes a workaholic in the newly established CIA, rarely seeing her. The marriage ends in divorce.
- Shut Up, Hannibal!: While neither is exactly a good person, Edward Wilson shuts up Joseph Palmi's politically incorrect posturing with a counter that's rather dismissive of minorities.Joseph Palmi: Let me ask you something... we Italians, we got our families, and we got the church; the Irish, they have the homeland, Jews their tradition; even the niggers, they got their music. What about you people, Mr. Wilson, what do you have?
Edward Wilson: The United States of America. The rest of you are just visiting. - Spy Fiction: Stale Beer-style.
- The Stoic: Edward Wilson is almost emotionally dead. This was possibly the result of witnessing his father's suicide, but as an adult he's closed off to his wife (whom he doesn't love anyway) and his son, barely has a reaction when his mentor is killed, and even sends his son's pregnant fiance to her death with no remorse.
- Truth Serum: Subverted in a disturbing, graphically realistic way. Edward Wilson, the head of the newly-formed CIA's counter-espionage branch, is confronted with a Soviet "defector" who may or may not be who he claims to be. In order to determine the man's real identity, Wilson has his men administer a brutal physical beating. When they still aren't sure, they use a newly-developed truth serum called "Lysergic Acid" (better known as LSD). Rather than the above-mentioned effects of "Hollywood" truth serums, the LSD does what you would expect from reality- the man babbles like an idiot and hallucinates. Later, when the drug begins to wear off somewhat, he delivers a "Reason You Suck" Speech to his interrogators... then jumps out the window to his death. In case you were wondering, he really was who he claimed to be, making the tragedy all for nothing, and highlighting the ineffectiveness of the so-called "truth serum". This was based on
a real incident where a man who was given LSD without knowing threw himself out of a window while hallucinating. He wasn't a Soviet defector, though, but a CIA agent given the drug by his own agency to test its effect on unsuspecting subjects.
