The Best Movie Massholes, in Honor of Pete Davidson’s Hilarious ‘Dumb Money’ Performance

After a wild blockbuster summer, Pete Davidson is back on the big screen, and the New York native has done the unthinkable: become a Masshole.

In the financial comedy Dumb Money (in theaters now), Davidson is part of a talented and diverse ensemble that includes Paul Dano, America Ferrera, Nick Offerman, Shailene Woodley, Sebastian Stan, Anthony Ramos and Seth Rogen. But many of the funniest moments in the film, which chronicles the infamous GameStop short squeeze, belong to the back and forth between Keith Gill (Dano), an internet personality who inspires other outsiders to invest in GameStop, and his stoner brother Kevin, a Postmates driver who steals Keith's car (and his customer's food) for deliveries.

In real life, Davidson can often be spotted sitting courtside at Madison Square Garden supporting his hometown New York Knicks. But in Dumb Money, he trades in his usual gear for the prototypical Masshole uniform, a.k.a. anything featuring the Boston sports teams. From the wardrobe to his lack of interest in work to his general bitter demeanor, Davidson's Kevin personifies the Masshole, a character that has long been a film staple.

For the uninitiated, a Masshole — a combination of the words "Massachusetts" and "asshole" — refers to a particular type of person from the Massachusetts area. Typically, they are decked out in Boston-related clothing, obsessed with their sports teams and struggle to pronounce the letter "R." The word was added to the Oxford Dictionary in 2015, and while it's defined as "a term of contempt for a native or inhabitant of the state of Massachusetts," it's also often used as a term of endearment. So, in that spirit, grab a Dunkin', forget about the Sox missing the playoffs, and join this Boston native in taking a fond look back at some of cinema's greatest Massholes.

Ben Affleck in Good Will Hunting

C'mon, you knew our favorite Boston boy had to be on the list! Long before he was the unofficial — and then official — spokesman for Dunkin', Ben Affleck was putting Massholes on the big screen map. Written by BFFs Affleck and Matt Damon, the South Boston and Harvard-set Good Will Hunting is littered with Masshole contenders, including Damon's math genius Will Hunting and Casey Affleck's perfectly-named Morgan O'Mally. But it's big brother Affleck who earns a spot on this list via his star-making turn as Chuckie Sullivan.

In one of the best performances of his career, Affleck gives himself two of the film's defining moments, proving that Chuckie is both the ultimate Masshole and a first-class ride-or-die buddy, with the latter often being a defining trait of the former (see The Town below). First, when filling in for Will during a job interview, Chuckie hilariously ensures that his friend will be taken care of financially. But that gesture pales compared to his "the best part of my day" monologue, in which the blue-collar character reveals previously unseen layers. Let's hope that Will never made Chuckie follow through on that threat of killing him — and that Chuckie is surviving in this post-Tom Brady Patriots world.

Dan Aykroyd and Daniel Stern in Celtic Pride

Written by New Yorker Judd Apatow and starring Maryland native Daniel Stern and noted Canadian Dan Aykroyd, on paper, the sports comedy Celtic Pride is missing that Masshole DNA behind the scenes. Its plot, however, is a Masshole fantasy come true: Two diehard Celtics fans kidnap their opponent's star player in the NBA Finals. (Not to endorse kidnapping, but we could have used a Mike O'Hara and Jimmy Flaherty when Steph Curry was torching us in the 2022 Finals!)

Mark Wahlberg in The Departed

Often overshadowed by Damon and Affleck in the "Famous Actors From Massachusetts" department, Mark Wahlberg has returned home a couple of times and always delivers standout showings, including in the biographical boxing drama The Fighter (more on that below). But it's his Oscar-nominated turn in Martin Scorsese's The Departed that earns him a spot on this list.

Wahlberg's Sgt. Dignam is the quintessential foul-mouthed Boston cop who delights in trash-talking criminals and his colleagues alike. Dignam takes an immediate disliking to Leonardo DiCaprio's undercover trooper Billy Costigan, telling him early on: "Hey asshole, he can't help you! ... I'm the best friend you have on the face of this earth, and I'm gonna help you understand something, you punk: You're no f---in' cop!" He also nurses a grudge against Damon's Colin Sullivan, whom he rightfully suspects is a rat. When Sullivan seemingly gets away with his crimes, Damon bides his time and does the most Masshole thing possible: Dons his best matching tracksuit and takes the law into his own hands.

Ted in Ted

Despite Wahlberg's bona fides as a native Bostonian and Oscar-nominated Masshole, he is thoroughly outdone in the latter department by a talking bear in this outrageous comedy from 2012. Ted writer, director and voice star Seth MacFarlane does have New England roots, which helps explain how he created the best Boston Ted since Red Sox legend Ted Williams. Whether he's smoking pot, being a general deadbeat, dating a Tami-Lynn, or never missing an opportunity to sing "Sweet Caroline," Ted is truly one of us.

Jeremy Renner in The Town

Have you ever seen the legendary shot (and meme) of Dwyane Wade throwing an alley-oop to LeBron James? Having delivered the perfect setup, Wade doesn't even need to turn around to know that James is going to slam it home. That is Ben Affleck and Jeremy Renner in The Town. Directed and co-written by Affleck, the heist masterpiece has so much going for it, from its electric direction to its electric performances (even Blake Lively held it down for the ladies of Massholedom). But the legacy of the hit film is Renner's unforgettable, Oscar-nominated performance as Jem Coughlin, the hot-tempered, coke and Xbox-loving sidekick to Affleck's bank robber, Doug MacRay.

Rocking his "sweatsuits and me against the world" attitude, Jem is like a pitbull itching to be let off his leash, as demonstrated in The Town's most often-quoted and memorable moment. Told by his new love interest (Rebecca Hall) that some guys have been harassing her, Doug, the leader of the "not f---ing around crew," goes to his best friend/muscle with a request. "I need your help. I can't tell you what it is, you can never ask me about it later, and we're going to hurt some people." Jem, watching TV, slightly shifts his eyes, waits a second, and replies, "Whose car we gonna take?" While there's so much more to Renner's Masshole Hall of Fame case, that gem easily solidifies his place.

All of the Sisters in The Fighter

Hey, women can be Massholes too! Wahlberg is once again outdone in that department in the sports drama The Fighter, in which he stars as real-life boxer Micky Ward, who hails from Lowell and might have the most Masshole family of all time. And while Christian Bale and Melissa Leo earned Oscars for their performances as Micky's drug-addicted brother and controlling mother, The Fighter's secret Masshole weapon is Micky's seven sisters, all of whom are always ready to talk sh-- or throw down. Also, shoutout to their pitch-perfect hair and accents. Speaking of hair, Conan O'Brien's sister, Kate, plays one of the siblings. And speaking of accents, Adams, who grew up an Army brat and never lived in the greater Massachusetts area, probably should have also won an Oscar just for keeping up with the natives.