The city: Main characters classified by intelligence

Several personalities meet The city. The film focuses on Ben Affleck’s Doug MacRay while his crew carries out robberies around Boston. They meet other characters outside the crew like Rebecca Hall’s Claire Keesey. The people the audience meets present their intelligence in their actions.

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The city is hailed by many as one of the greatest robbery films ever made. The plot stems from these robberies, and some characters show their cleverness during these intriguing sequences. Others present their sense in the other actions of the film.

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Krista “Kris” Coughlin


Kris is Doug’s ex-boyfriend. Blake Lively plays Kris in one of her highest rated roles. She presents her intelligence in the actions she takes. Her foolishness is shown several times throughout the film. When Agent Frawley talks to her at a local bar, she fails to discern his cunning.

Kris shows his lack of emotional intelligence through his outbursts in confrontations with Doug. She is too fat-headed to deal with his constant rejections. She lacks foresight, drives her car with her child when she is drunk, and lands her in the hospital. Crisis rarely presents intelligent moments.


Stephen “Big Mac” MacRay


Chris Cooper uses a prison phone wearing glasses in The Town.

Big Mac is Doug’s father, and audiences hear more about the character than they see him on screen. Big Mac gives Chris Cooper one of his highest rated films. Mac is introduced as he and Doug talk through a glass wall in prison. He is less developed than many of the characters in The city, but fans learn his intelligence from his actions.

When Big Mac talks to Doug, he shows his lack of emotional intelligence with his numb attitude and inability to understand Doug’s concerns. Moreover, he foolishly crosses the powerful florist, resulting in the destruction of his family.

Albert “Gloansy” MacGloan


Shared image of Gloansy in The Town.

Slaine’s Gloansy is one of the members of Doug’s crew. He’s a supporting character. However, he presents his wisdom a few times. When he is questioned by the police, he presents his lack of education. When asked to read lines fed by police, he tells them he is trying to make them sound “genuine” and searches for the word “authentic”.


He presents various skills, such as excellent driving, which require certain prudence. He also comes up with the final plan to rescue Doug during the Fenway Park robbery. He creates a distraction by driving an ambulance while Doug and Jem slip out of a side door in police uniforms. His smart moments, however, are sporadic.

James “Jem” Coughlin


Ben Affleck and Jeremy Renner sit and talk in The Town

Jeremy Renner’s Jem is one of Doug’s good friends. He shows his lack of emotional intelligence in his violent outbursts and short temper. However, he also highlights his wisdom in several actions. He helps plan the robbery and presents his quick mindset in their operation.

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Jem is not the most likeable character in The city. However, he shows intelligence in some of his insidious behavior. After the first robbery, he shows foresight and wants to be sure there are no eyewitnesses, knowing they have the potential to put him in jail.

Claire Keesey


Shared photo of Rebecca Hall smiling in town.

Claire is Doug’s love interest, played by Rebecca Hall. She is presented after witnessing the first robbery at her job as the bank’s assistant manager. She is pleasant, but shows her lack of wisdom in her naivety.

She blindly trusts Doug, unable to find out he is involved in the robbery until FBI Special Agent Adam Frawley reveals his identity to her. However, she shows her emotional intelligence when she stands up to Doug after learning the truth.


Fergus “Fergie” Colm


Fergie holds a rose in The Town.

Pete Postlethwaite’s Fergie is a powerful member of the Irish mob. Also known as the “florist”, he organizes jobs for Doug and his crew. His personality is most evident in his confrontation with Doug after he tries to back out of the Fenway Park robbery.

Fergie speaks eloquently as he threatens Doug. He uses intimidation and says just the right things to scare Doug into working at his job and succeeding in the process. He gives the extra detail of sending a funeral to him, which underscores his critical thinking. But his arrogance fuels his mind from preparing for Doug’s revenge, which leads to his death.

FBI Special Agent Adam Frawley


Shared photo of Jon Hamm in the City.

Agent Frawley is leading the investigation into Doug’s crew. Jon Hamm plays the character, and his wisdom is expressed in his hunt for Doug. He tricks Kris into giving him information at the bar after telling her he works for the FBI, knowing she will think he’s joking.

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He is able to put together clues and expose the Fenway Park robbery, which takes almost every member of the team down in the process. However, he is not smart enough to oversee Doug’s final plan for escape.

Douglas “Doug” MacRay


Ben Affleck’s Doug is the main character and reveals himself as one of the film’s smartest characters. He presents his lack of emotional intelligence in his outbursts with Kris, Jem and Fergie. However, he shows his intelligence in his calculated robberies.

Doug is spotlighted as one of The city‘s brightest characters at the end of his bow. He manages to outwit Frawley and the FBI and escape Boston. He thinks ahead and manages to send Claire some of his money. In addition, he cleverly leaves the trail of a mandarin to signal where he wants to be in Florida so Claire can come to see him while the FBI is no wiser.

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