The Boston Masshole

What’s the most annoying trope in books or movies?

Listen, one thing I know about is Massholes. I grew up with plenty of them. I know when the accent is real.

In movies, they never get it right. Even Matt Damon and Ben Affleck, who grew up in highbrow Cambridge, don’t get it quite right. (Despite that slight flaw, I loved the film Good Will Hunting. It captured one of the key characteristics of Masshole mentality—class awareness. “You think you’re bettah than me cuz you go to Hah-vahd? Well Faaaack you”)

Mark Wahlberg, on the other hand, is an objectively terrible actor, but an authentic Boston Masshole. Did you know he grew up in the infamous South Boston “projects” and was involved in a number of serious racially-motivated assaults and harassment incidents as a teenager in Boston during the mid-1980s? I did! He’s the type of guy I would’ve avoided like the plague in high school.

This is a famous image by Stanley Forman. Titled “The Soiling of Old Glory,” the photo won a Pulitzer Prize for breaking news photography. Forman took the picture on April 5, 1976, for what was then the Boston Herald American. A young white man lunges at a black man (Ted Landsmark) with the sharp point of a flagpole, with the American flag attached.

Well, this is all a long-winded way of saying that I finally saw an authentic portrait of that trope last night. The film Tony about one summer in the life of the late celebrity chef Anthony Bourdain has a great Masshole character played by Leo Woodall. He’s SO good in this. In my opinion, he steals the film, which is largely set on Cape Cod in the summer of 1975. His accent and demeanor are perfect. It just figures that he’s a Brit! He totally nailed his part. GENXers should go see the film for Woodall and the soundtrack (including some classic Jonathan Richman) alone.

Leo Woodall as the Masshole character—a restaurant worker named Sal—in Tony (in theaters now)
Here’s me at a dinner with Ted Landsmark (from the Pulitzer Prize winning photo) in 2013. It was an honor to meet such a distinguished Bostonian.

The late comeback

Daily writing prompt
Write about a time when you didn’t take action but wish you had. What would you do differently?

I’m not typically someone to not say something. I will speak-up when needed. I trust my instincts.

For example, when an ambulance (with no siren or lights in use) nearly ran over a woman in a Boston crosswalk, I made a mental note of the name of the ambulance company (which was from a different part of the state), called the main office, and got the driver in trouble. Another time a FedEx driver (a complete stranger) beckoned my young son to his truck when he was walking by himself and asked him to carry a package up the driveway. I got that guy in trouble too.

Being a native-born Masshole who participated in the hellish Boston commute for decades, I’ve also been involved in my fair share of road rage flare-ups. I’m quick to flip the bird to the deserving. I’ve been involved in one or two shouting matches with other drivers while sitting at traffic lights.

One time two young men with a Harvard window sticker cut me off dramatically on a winding thoroughfare, only to end-up at the exact same ATM as me minutes later. I went up to them and said, “Did they teach you to drive like that at Harvard?”

The only times I remember regretting not saying something are when I couldn’t think of a comeback fast enough. I hate that.

Ponytail Harvard guy from “Good Will Hunting”

Click here to watch the best comeback in the film.