Danny Quinn (Donnie Wahlberg) is a former "street kid" from South Boston, colloquially known as "Southie," who returns home from New York City after three years away. He finds his mother (Anne Meara) overwhelmed with worry as her other three kids are caught up in the madness of the hardscrabble neighborhood in which drinking, sex, and fighting is the way of life. Danny tracks down his brothers only to find out they are deeply embedded in the Irish mob in Boston and in debt to local mobster Colie Powers (Lawrence Tierney). His younger sister Kathy (Rose McGowan), meanwhile, became a barfly in Danny's absence.
Danny must get his hands on some quick cash in order to stop his brothers from getting their legs broken and his sister off the streets. In his pursuit to help his ailing mother and right his family's name on the streets of Southie, Danny tracks down his old girlfriend from the neighborhood, Marianne (Amanda Peet), finding that the love he left behind still remains. She tells how she heard about the gunfight he was in with Joey Ward (Jimmy Cummings) and wants to know if that is why he left town. Danny confesses that real reason he left town was that he needed to stop drinking if he were to become the man that she would want him to be.
Unable to find legitimate work and banned from union jobs due to a scuffle at a wedding, Danny becomes desperate for money. Two of his old pals know Danny needs money and offer him an opportunity to be a partner in an underground gambling club, though, they neglect to tell Danny that their silent partner is his old nemesis, Joey Ward. It does not take long before Danny finds out and he and Joey are face to face. In Danny's absence from the neighborhood, Joey's father Butchie has declared war on Colie Powers and without knowing this Danny finds himself caught up in the middle of their war as it looks like he is in business with the Wards. The mob war eventually comes to Danny's front door, and the stress of an attempted murder in front of his house kills Danny's mother.
Southie was written by two young screenwriters from Boston, Jimmy Cummings and Dave McLaughlin. It was originally entitled "Brass Ring".
The lead role was originally offered to Mark Wahlberg but he was not available following the success of the 1997 film Boogie Nights. Cummings' younger brother, Dan, suggested Donnie Wahlberg for the leading role. Shea spent a day with Ron Howard in New York as Howard completed the sound mixing on the 1996 film Ransom, in which Wahlberg had a supporting role. Shea liked what he saw and Wahlberg was offered the role.
Shooting was scheduled for February 1997, in the middle of a very cold and brutal Boston winter. The film was shot with a full union crew in twenty-four days.
After almost a year of post-production editing and scoring by composer Wayne Sharp, the filmmakers changed the film's name to Southie at the suggestion of Donnie Wahlberg. It was the first feature film ever shot entirely in the old South Boston neighborhood, a place once described as "the last white ghetto in America".
