These are what we call the 'YMMV items.' Things that some people find in this work. We call them 'your mileage might vary' because not everyone sees these things in the same way. This starts discussions in the trope lists, a thing we don't want. Please use the discussion page if you'd like to discuss any of these items.
YMMV: The Town
Award Snub: The film did not get a Best Picture nomination.
In an interesting way, Doug can be seen as a much darker take on Neil McCauley from Heat. Both men are the main characters and career criminals who rob banks. But after they plan to retire from their criminal life, both also plans to flee the cities they're living in with the woman they encounter in their lives.
Claire and Eady. Both women are lovers to the criminal protagonists. But after finding out that the men they fell in love with happens to be living a criminal life, both were forced to leave them when they're on the verge of being caught by the police.
Darkness-Induced Audience Apathy: Given the gritty nature of the film, it can be hard to root for any of the characters in the cast, up to and including Doug himself.
Harsher in Hindsight: The death of Fergie - death by Groin Attack no less - becomes a lot less gruesomely funny when you remember that Pete Postlethwaite died not long after filming ended.
He Really Can Act: Ben Affleck restored faith in his acting abilities and Blake Lively proved there is more to her than Serena van der Woodsen. Everyone knew Jon Hamm could already act but this showed he could go all the way.
Moral Event Horizon: You know Fergie is a goner when he tells Doug that he hooked his mother on coke and indirectly caused her suicide.
One-Scene Wonder: Chris Cooper as Doug's father, Stephen MacRay. Also, Pete Postlethwaite is on screen for hardly more than 5 minutes, but makes the most of every moment in an intense, genuinely frightening performance as Fergie the Florist.