Originally the filmmakers were considering making a crime caper movie in the vein of Lock, Stock and Two Smoking Barrels (1998) or Snatch (2000) called "Imperfect Crime," many characters from which made it into "Beantown." Ed Zeppelin, Sheep-Shaggin' Sean, Fancy Dan Medici and others were originally from that script, as were several of the gags including that of a character continually fixing himself up with duct tape and other objects as he is more and more injured.
Many of the character names in the film are references to history, traditional music, and pop culture: -Molly Finn gets her first name from the Celtic rock band Flogging Molly. -Sergio "The Director" is clearly named after the Italian director, but the Leone family is also a reference to the video game Grand Theft Auto III (2001). -Fancy Dan is named after an obscure Spider-Man villain and the infamous Medici family from Renaissance-era Italian politics. -Jimmy "The Weasel" Fratianno is the name of an infamous Mafioso stoolpigeon. -Mikey Killeen takes his surname from the Killeen brothers of Boston's Irish Mob Wars of the 1960s. -Dion Moran takes the first and last names of two members of Chicago's Prohibition-era Northside Mob: Dion O'Banion and George "Bugs" Moran. -Ed "Zeppelin" Battimo takes his name from the rock band Led Zeppelin. -Alphonse Machiavelli clearly takes his name from the infamous author of "The Prince." -Silvio Manfredi is the real name of the Spider-Man supervillain Silvermane. -Tony Lupino is named after one of the bosses from the computer game Max Payne (2001). -Fry McFly takes his names from the lead characters of the television show Futurama (1999) and the Back to the Future (1985) film series. -Speranza "Snakes" Zilioni takes his nickname from the fake gangster movie made for the film Home Alone (1990). -Slaughter O'Toole is a name taken from the traditional Irish song "The Irish Rover." -Il Mercenario's name is taken directly from the title for The Mercenary (1968). -Big Joe Vanzetti and Frankie "Shades" Sacco take their names from the famous Italian anarchists Sacco and Vanzetti. -Dublin O'Shea is the name of the titular character from the traditional Irish song. -Spike O'Donnell was the name of another Prohibition-era Irish mobster from Chicago, and was similar in name to the South Boston Irish gangster Spike O'Toole. -Tim Finnegan was the name of the corpse from the traditional Irish song "Finnegan's Wake." -The Fallon Brothers are named after the criminal Fallon from the Daredevil comics. -Bobby "Jaws" Killane takes his nickname from the famous henchmen of the Roger Moore Bond films. -Dicey Riley takes his name from a song by the Tossers, another Celtic rock band. -Blackie Flanagan takes his first name from the obscure Spider-Man villain Blackie Gaxton. -William "The Kid" McBride's name comes from the traditional Irish song "The Green Fields Of France." -Vitale's bodyguard Pietro "Mustache Pete" Morricone takes his nickname from the 'Mustache Petes,' a group of Old World Italian gangsters who immigrated to America during the early 20th Century, and his surname from the famous Italian composer Ennio Morricone, who scored many of Sergio Leone's films.
The BMW used in the opening credits was found through Craigslist. The shots of Bob Ondek riding inside the sedan were shot with another car in downtown Manchester, CT, while the shots of the car itself were shot in Boston a year later.
Director Timothy Norman let actors name their own characters if they wanted to in return for their free performances.
Kristen Savage and Matt Reardon's scene in the hockey rink scene was shot during the summer when the rink was empty, and the hockey game and spectators were filmed much later. The summer footage became damaged, and director Timothy Norman had to go through each shot frame by frame to repair it.