40×40: The Boondock Saints (1999)

Written and directed by Troy Duffy.

“I’m not the rope-toting Charlie Bronson wannabe that’s getting us lost!”

Why Did I Get This?

I saw this film at 17 when dual-wielding silenced pistols, smart-alecky dialogue and brual violence were right at the top of my viewing agenda. As I recall, it was on Sky at around the same time as the excellent The Jack Bull, and might’ve benefited from funding from the corporation – it was certainly billed as a Sky Original, or something similar, when I saw it.

Obviously, I knew Billy Connolly and was aware of Willem Dafoe. I knew Sean Patrick Flanery from The Young Indiana Jones Chronicles, but Norman Reedus was yet to hit big as Daryl in The Walking Dead. I knew nothing of the writer/director Troy Duffy, though I understand the documentary about him is fascinating and doesn’t show him in a great light (I’ll endeavour to seek it out down the line, I promise).

Whatever the behinds the scenes stories, to me The Boondock Saints was a tough, straightforward action film, with cool imagery and cooler shootouts, and one I crowed about whenever I could.

Will it hold up? Honestly, I do remember there being quite a bit of… let’s say problematic moments and attitudes in the film, but maybe I’m misremembering.

Let’s find out.

The Late Review

As always, the Late Review will include spoilers from the film. If you’d like to avoid them, scroll straight down to the next heading!

Boston Irish brothers Connor and Murphy MacManus (Sean Patrick Flanery and Norman Reedus), get into a bar fight with Russian mobsters on St Patrick’s Day. When the gangsters return for revenge, the brothers kill them in self-defence, then inadvertently become local heroes as they rage what they feel to be a righteous war against organised crime in the city. FBI agent Paul Smecker (Willem Dafoe) is tasked with working out who is murdering the city’s mobsters, but finds himself questioning whether he really wants to bring them to justice.

The late 1990s saw a slew of violent, stylish thrillers where young men in cool coats bungled their way through dangerous situations and came out swearing and dual-wielding silenced pistols (because that’s the coolest a handgun can look). This one, for me at least, was one of the more memorable, and not just for the overblown religious imagery and prayer of execution that is surface-level cool but has no doubt led to more than one regrettable tattoo in the last couple of decades.

Watching it back now, and it has a lot going for it – the upbeat music, Irish-American stereotypes and sweeping shots of Boston feel very much like The Departed (which, in fairness, is the better film), Reedus and Flanery bring a great energy to their characters (though the accents are less than stellar), and the recurring trick where we cut away before the shootouts begin to have the blanks filled in by Agent Smecker’s preternatural ability to assess and reconstruct a crime scene is a genuinely nice approach.

Where The Boondock Saints stumbles is with some of its boorish behaviour and mixed messaging. Violence, it suggests, is the only answer to society’s problems, but within the space of a couple of lines, the characters are mocking the macho bullshit the movie is celebrating. But then maybe that’s the point, it’s not as simple as black and white?

It couldn’t be more of a lads film if it tried, and maybe looking back from 2022 it’s easy to cry ‘different times’ or ‘nonsense snowflake wokery’, but when homophobic slurs are flying around left, right and centre – even from one of the gay characters – the script really does feel, for want of a better word, unpleasant.

To his credit, Duffy’s decision to make his lead investigator and smartest man in the movie gay could be seen as quite forward thinking, and Dafoe looks to be having a good time with the character – a sort of Cumberbatch-era Sherlock who can reverse-engineer a crime scene then walk the viewer through it. But while including a level of apparent self-loathing could be seen as offering some depth to the character, to me it comes off as disappointingly nasty or dismissive.

An early line about Billy Connolly’s boogeyman hitman character Il Duce states that he’s a monster, but doesn’t kill women or kids – all very morally sound for a multiple murderer, but the line sticks out as a lead-up to Dafoe’s dragged-up assault on the mob boss’s home to save the brothers at the end.

Yeah, this bit felt a bit much, as we’re treated to Smecker acting as a hooker to distract the goons, writhing around on the floor urging them to get undressed before gunning them down, adjusting his wig in the mirror and admitting he’s gone too far.

Still, it means he just gets knocked out by Connolly’s character instead of being killed, as Il Duce only sees the short dress and wig – it’s a neat payoff, in fairness.

Connolly’s character even gets a second, later payoff, in the movie’s third act.

Released from one of those highest of high security prisons that only exist in heightened crime movies, Il Duce is a silent hitman hired by the mob to take out whoever is killing their goons – the MacManus brothers are completely unaware of his existence, and work their way from slaughter to slaughter almost at random… but they are assisted in their later missions by their friend and low-level hood, Rocco (David Della Rocco).

Rocco is a peon who barely registers on the mob boss’s radar, except for his reputation as a funny man, so when he delivers a sandwich to the big guy, we get a riff on the Goodfellas “funny how?” scene, as he’s forced to tell a joke to the boss and his right-hand man (played by Ron Jeremy – nice to see him meet a sticky end, considering some of the stories about him in recent months).

As the bodies pile up, the assumption is only a disgruntled insider could be targeting these goons, so Il Duce is pointed at Rocco. When he joins the brothers in an assault on the boss’s home, the three are captured and tortured and Rocco is killed, though not before he urges the lads to continue their holy war and never stop.

Devastated but ready to shed more blood, the brothers say their family prayer over Rocco’s body as Il Duce enters the room, pistols aimed… only to join in the prayer and reveal he’s their long-lost dad!

Does it feel a bit out of the blue? Yeah, kinda. But it feels about right for this sort of wish-fulfilment, vigilante-pardoning, late-90s actioner.

The closing scenes see the reunited family stroll into a courthouse where the boss is expected to be acquitted for his many crimes, casually tossing their weapons over the metal detector, before forcing the packed courtroom to witness them execute him for his crimes and as a warning to other evildoers.

It’s worth mentioning that the film opens with a church service recounting the story of Kitty Genovese – who was raped and murdered while locals turned a blind eye and neither came to her aid or phoned the police.

The message is ‘the only thing necessary for the triumph of evil is for good men to do nothing’, so the MacManus brothers do something.

But then, what does that say about Smecker, who comes to respect them for doing what the law won’t allow? Do his actions (in aiding the vigilantes), and inaction (by allowing them to murder a man in front of a crowd), make him a good man or an evil one?

Metaphorically, he’s looking the other way, but in the final scene in the courthouse, he forces himself to watch the murder take place and looks visibly appalled by it.

It’s a genuinely interesting quandary, and as the credits roll we’re treated to a stack of local news voxpops arguing for and against the vigilante brothers – it feels like Duffy has something interesting to say about society, whatever your thoughts about how he says it.


With its attitude, violence and mixed messaging, The Boondock Saints occasionally felt more dated to me than some of the films twice its age I’ve rewatched for this site.

Was it enjoyable? Yeah, aside from the racial and sexual slurs, dubious attitudes towards LGBTQ+ lifestyles and attitudes towards women, I suppose it was.

Women really do get short shrift here. There’s no doubt in the script or direction that the manly men are very much the heroes in this movie, and the women are either drug addicts, strippers or a butch caricature with ideas above her station.

The only female actor given anything close to a respectable character gets two lines as a forensics expert before getting bawled out by Willem Dafoe because the blood she’s testing has been covered in ammonia and is useless as evidence.

Questionable attitudes aside, The Boondock Saints is a fun ride, and Troy Duffy had the bottle to make exactly the film he wanted (even if what it wanted to be was filled with echoes of many other films). I’m curious to see the sequel, which I’d probably watch before Overnight (the documentary about Duffy and the making of the first movie), and the world of the MacManus brothers certainly seem ripe for further adventures.

The leads are engaging and fun, there’s a swagger and confidence to the movie that feels brash but genuine, and sucks you in for the 90-odd minutes it lasts, and while it’s not exactly a John Wick universe, it’s got that kind of a heightened feel to it that could be interesting to explore further.

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