Jon Hamm (The Town) The Town
Jon Hamm plays Special Agent Adam Frawley, the FBI case agent pursuing Doug's crew. Frawley is the film's ticking clock -- every scene with him tightens the timeline Doug has left. Hamm, then at the peak of his Mad Men fame, took the role specifically because it was the opposite of Don Draper: a man who lives entirely for his work, with no double life and no hidden self.
Hamm wanted a role that was the opposite of Don Draper
By 2009, Hamm had received dozens of scripts casting him as variations on his Mad Men persona. Frawley offered something different.
"I had also seen Dahmer. And I was like, 'Who the hell is this guy? He's crazy.'" — Jon Hamm, on first encountering Jeremy Renner's work, The Ringer (2020)
Hamm's version of Frawley is relentless without being villainous. The film does not frame the FBI agent as wrong -- he is pursuing criminals, and his methods, while occasionally cruel, are professionally sound. The interrogation scene with Doug (beat 25) is the performance's centerpiece: Hamm delivers Frawley's threat -- "You are going to die in federal prison" -- with the measured confidence of a man who has said it before and means it every time.
After receiving "about 40 scripts that were all set in the 60s, or had me playing advertising guys," Hamm was relieved to play a contemporary law enforcement officer whose entire identity was his job. (seattletimes)
He researched the role with real FBI agents in Boston
Affleck insisted his cast immerse themselves in the real counterparts to their characters. Hamm spent time with federal and state law enforcement officials in Boston, studying the rhythms of investigation work.
"It was a tremendous advantage to be able to hang out with and talk to several of the law enforcement officials in Boston, both at the federal level and at a state level and local level." — Jon Hamm, Massachusetts Film Office (2010)
The research shows in the procedural details. Frawley's method is transactional -- he trades prison time for intelligence, working his way up the chain one frightened informant at a time. His approach to Krista (beats 36-37) is calibrated with surgical precision: charm at the bar, then the knife at the hospital when she is most vulnerable.
The interrogation scene gave Hamm his Pacino moment
Critics compared the Doug-Frawley interrogation to the famous coffee-shop scene between De Niro and Pacino in Heat. The comparison is structurally apt: both scenes put the criminal and the lawman face to face and let the tension come from mutual recognition rather than physical threat. The difference is tonal -- Mann's scene has respect between equals, while Affleck's scene has contempt from a man who knows he has the advantage.
Hamm plays the scene as professional pleasure. Frawley enjoys the hunt not sadistically but with the satisfaction of a craftsman doing his best work. His promise to Doug -- "I just want you to know that it's gonna be me who tells you to go fuck yourself" -- is delivered with the quiet assurance of a man who has already won and is simply informing his opponent of the timeline.
Hamm described empty Fenway Park as surreal
The Fenway Park sequences gave Hamm access to spaces the public never sees.
"There's nothing weirder than an empty stadium... I'm getting to see something not many people get to see." — Jon Hamm, The Ringer (2020)
Hamm's warmth extended to the cast. He described Pete Postlethwaite's presence on set with evident affection:
"He just smiled as broad as he could, and he's like, 'Come on, sit down, have a drink.'" — Jon Hamm, on Postlethwaite, The Ringer (2020)