Danny Quinn is a former "bad boy" from South Boston who returns back home after living in New York for three years and he quickly gets involved in troubles between his irresponsible friends, who are supported by one Irish mafia clan, and his family whom include his equally irresponsible sister and widowed mother, who are members of another Irish-American mob clan.
Southie was originally written as "Brass Ring" by two young first-time screenwriters from Boston, Jimmy Cummings and Dave McLaughlin. In 1995 they brought their screenplay to New York where it was given by the original producer, Merrill Holtzman, to Shea to read. Shea met with Cummings and thought that the script was "full of promise". Shea felt that Cummings and McLaughlin, who had both grown up in Boston, had captured the flavor of the dialogue and of the characters in the Irish American community but felt that the beginning of the movie and the original ending, in which Danny Quinn kills Joey Ward needed to be changed. Over the next year, Shea spent time in South Boston with Cummings getting to know the neighborhood that Cummings had grown up in, worked with the writers on the screenplay and eventually agreed to direct the film. During the next year they continued to write in partnership as they scouted locations and put the pieces of the film production together.
The lead role was originally offered to Mark Wahlberg but when his film "Fear" became a hit the production could no longer afford him. Cummings had the idea of approaching Mark's brother Donnie Wahlberg who at that point had only played minor roles in movies. Cummings met with Donnie and the two hit off. After spending time with him Cummings called Shea, they met with Wahlberg and Shea realized that Wahlberg was, in many ways, born to play the role. At the invitation of Ron Howard, Shea spent a day watching Wahlberg do vocal dubbing for scenes from Howard's film "Ransom" in which Wahlberg had a supporting role. Wahlberg was then offered his first starring role without an audition. He was already a star in the music business as a member of the Boston singing group "New Kids on the Block" but was ready to test himself as a serious actor. Independent financing came from young producers, Bill McCutchen and Hugh Wilson. Shea then offered the lead female role to Rose McGowan and the rest of the cast fell into place. Amanda Peet joined the cast in Boston just before production began. Will Arnet was a friend of Cummings in New York and Anne Meara, a friend of Shea's, agreed to play the key role of the mother of the Quinn clan.
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. Many of the people in the film had never acted before but Shea wanted the real-life quality they possessed and tried to bring out their natural talents. Sue Costello, Bo Cleary, Phil Barineau, Steve Sweeney, Jere Shea, Robert Wahlberg (Donnie's real older brother), Jay Giannoni, Jeffery Cook, Steve Koslowski, James Cummings as the antagonist Joey Ward, and others all make their feature debuts. In addition to Donnie Wahlberg in the lead role of Danny Quinn, Rose McGowan was cast in the supporting part as Danny's sister Kathy, as well as Anne Meara in the role as Danny's mother. Amanda Peet played a minor role as Marianne, Danny's former girlfriend, and veteran character actor Lawrence Tierney was cast in a small role as the aging Irish Mafia boss Colie Powers.
Celebrated jazz drummer Johnny Blowers also makes an appearance in The Quencher tavern, "telling Sinatra stories." The film ends as the real St. Patrick's Day parade goes through South Boston. The film makers were given permission by Thomas Menino, the Mayor of Boston, to shoot the parade, the first time that had happened. Directors of photography Allen Baker and Michael Bulter used five 35mm cameras, some of them hand-held and hidden on the parade floats.
After almost a year of post-production editing and scoring (by composer Wayne Sharp) in New York the film makers changed the film's name to "Southie" at the suggestion of 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" and the home of the Irish mafia headed by the controversial James "Whitey" Bulger, called in the film "Colie Powers" and portrayed by Lawrence Tierney in his final screen performance. In 1998 "Southie" won Best Picture (The American Independent Filmmaker Award) at the first festival it entered, The Seattle International Film Festival. It then played to sold out houses at the Nantucket Film Festival, the AFI Festival in Los Angeles, and was acquired for distribution by Lions Gate Pictures after its screening at the Montreal Festival du Monde where it represented the United States in the main competition. In April 1999 it played at the 14th Dublin Film Festival. Critic Padraig Browne wrote in the Irish Times: "Shea directs with a nice lean style and Wahlberg shows that he's every bit as good as his brother, Boogie Nights' Mark."
Film critic Jay Carr of The Boston Globe wrote that the film had "heartfelt urgency" with "an intense individual and communal commitment that seems to boil up from the streets." James Verniere of the Boston Herald gave it three stars and wrote that there were "powerful performances" with an "electric charge especially by leading man Donnie Wahlberg."