I think the characters in The Town were portrayed realistically along with the culture. There definitely was a flower shop in Charlestown that fronted for various activity in real life. And there was definitely a culture where bank robbery was a legitimate career option. I don't think there was a guy actually from Ireland that was in charge though. The real life crews were legit hard guys and definitely did a lot of planning for some of the jobs.

But robbing Fenway Park in broad daylight? All Hollywood. And nobody started dating the bank teller after they robbed her either.