7 Great Movies Centered Around Boston’s famous “Southie”.

7 Great Movies Centered Around Boston’s famous “Southie”.

January 17, 2020

If you grew up in or around the greater Boston area you no don’t have visited South Boston, and probably have a pretty interesting story about an experience there. For decades South Boston has earned many reputations, from being home to some of Boston’s most hardened citizens to a crazy place for locals to drink too much and party too hahd. Southie is one of the most unique parts of Boston and apparently Hollywood agrees, centering movies around this historic area for decades. We decided to pick 7 of our favorites that used South Boston as it’s backdrop. If you haven’t seen one or two of these movies you can probably find them streaming somewhere for free, and we highly, highly recommend watching them all.


Good Will Hunting (1997): For many non Boston area natives, this movie served as their introduction to South Boston, and of course the accent we all speak so well. The main character lived on the West Side (aka the Lower End), and he and his boys would like to hang at Woody’s L Street Tavern. Due to cost concerns, and Hollywood being a bunch of cheap pansies (probably to scared to do much filming in Southie) much of the movie was filmed in Toronto, Canada. There are still a few recognizable exterior shots of South Boston, such as the baseball field off East First Street and the district courthouse on East Broadway. But we couldn’t figure out why someone as “smaht” as Will Hunting would take the Red Line to Cambridge via Dorchester? Although that mystery will be lost to time we still think this movie is worth a watch any day.

How dah yah like them apple’s?

Southie (1999): One of the great Boston based movies actually filmed mostly in and around Southie is a movie with a truly clevah name “Southie”. South Boston’s history with organized crime, and the reign of James “Whitey” Bulger in particular, gets a cinematic reference in this relatively low budget flick featuring Donnie Wahlberg, Rose McGowan, Amanda Peet and a young, Will Arnett. Arnett actually plays a character named “Whitey” but the Bulger stand-in here goes by the name of Colie Powers, and is a little bit older than Bulger would have been if he wasn’t already on the lam at this point. Important scenes were shot at the late, departed Quencher Tavern (oh we will miss you!) and the still-intact Mul’s Diner and South Boston Bowlarama.

Boondock Saints (1999): Editors Choice. This is somewhat of a an albino tigah if you will. A truly rare South Boston, that in fact has no scenes filmed, at all, in Southie. No unfortunately the filming in Toronto and claiming it was South Boston theme doesn’t end here, but the directors did toss Boston a bone and include some shots of Copely Square. Anyways, this tale follows two vengeful Southie (Irish) brothers, accompanied by one dumb Italian friend,  looking to rid the city of mobsters (one of them is a youthful Norman Reedus, of “Walking Dead” fame). There are obviously some echoes of Whitey Bulger’s takedown of the Boston mafia, including the FBI agent played by Willem Dafoe — classic line: “There was a firefight!” — who decides to help the brothers out. They end up defeating all the evil mobsters and living happily evah aftah, until they created Boondock Saints II, what a shame.

Mystic River (2003): Finally a movie keeping it real! (Maybe it’s a milleneal thing?) Clint Eastwood film Mystic Riverwas filmed all over Boston, not just Southie (Eastwood to be brave enough to film on Southies’ mean streets). Yes, we get Miller’s Market on K Street but there’s Doyle’s and Franklin Park, and of course the titular river. This film can make Southie feel a bit disjointed, a bit unfamiliar, that’s intentional based on the original novel. “Mystic River” takes place in a fictional neighborhood, East Buckingham, intended to be an combination of Southie, Dorchester, Brighton and Charlestown. But the neighborhood’s insular nature and the way the characters’ respective past follows them are trademark characteristics of Hollywood’s depiction of South Boston.

The Departed (2006): “The Departed” is the first Hollywood blockbuster inspired by the neighborhood’s most infamous criminal, James “Whitey” Bulger. Although the filmmakers did a decent job of keeping it real, and filming a lot in or near the neighborhood, particularly the Fort Point area and the Neponset bike path in Dorchester, much of the movie was shot in our much despised rival to the South, New “mother-f*cking” York. That shop where young Colin meets Whitey stand-in Frank Costello (Jack Nicholson)? (writer vomits) Brooklyn. The bar where Billy Costigan (Leonardo DiCaprio) meets up with Mr. French (Ray Winstone)? (writer still wreching) Still Brooklyn. The bar that Costello uses as his HQ? The exterior is on Charles Street, here in Beacon Hill, but the interior is in Manhattan. Either way this is a true Boston film classic, and if you haven’t seen it go watch it today. Thank us latah.

Gone Baby Gone (2007): Ben Affleck makes his directing debut, and the Dennis Lehane characters Patrick Kenzie and Angela Gennaro make their big screen debut. Kenzie and Gennaro are Dorchester denizens, but a key scene unfolds in South Boston when Remy Bressant, the character played by Ed Harris, attempts to stage a (faked) robbery at Murphy’s Law at the corner of E. First and L streets. Kenzie, played by Ben’s younger brother Casey, tracks a wounded Remy to a nearby rooftop, where he dies. The view from that building is recreated on the movie poster, showing a somber Kenzie staring downward with the Back Bay skyline as a backdrop.

What Doesn’t Kill You (2008): This independent flick was written as a largely autobiographical screenplay co-written by Southie native Brian Goodman, an actor who also directed the film. The story about a man trying to break free from a life of crime and do right by his family starred Mark Ruffalo and Ethan Hawke, as well as Amanda Peet and Donnie Wahlberg who walked these streets once before in “Southie.” Unfortunately, the company that was going to distribute “What Doesn’t Kill You” filed for bankruptcy, and the movie never got the wide showing it deserved. So find it and check it out today. And hey they filmed a lot of it in Southie!

Hope you enjoyed out list. Have a wicked pissahh day!

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