The somewhat taller, more prone to thinking things through of the MacManus twins.
- Anti-Hero: He may be a wanted murderer, but he only goes after criminals who are running free in the streets and members of various mafia.
- Berserk Button: Do NOT mess with his brother.
- Big Brother Instinct: Despite the fact that they are, in fact, twins, Connor shows a much more protective attitude towards his brother than Murphy does towards Connor.
- I Know Mortal Kombat: Many of his plans come from movies or TV shows he saw.
- Improvised Weapon: After managing to pull a toilet right out of the floor, Murphy drops it onto one of the soldiers of the Russian Syndicate from the roof.
- Large Ham/No Indoor Voice: While Connor does have his quiet badass moments (such as during the "kill 'em all" speech at Rocco's place), when he gets going, he can get pretty loud.
- Never Hurt an Innocent: He makes this point perfectly clear when Rocco puts a gun to a priest's head during confession... by doing the exact same thing to him.
- N-Word Privileges: Romeo only gives him one pass at (jokingly) calling him a "greasy spic".
- Politically Incorrect Hero: In the sequel, he uses some derogatory terms for gays and Mexicans, but it's mostly just him fooling around than being genuinely prejudiced.
- Foolish Sibling, Responsible Sibling: Not by much, but Connor is generally more calm, level-headed, and inclined to have a plan, except for in certain desperate situations.
- Red Oni, Blue Oni: Blue to Murphy's Red. Connor can be a lot more soft-spoken and less violent than Murphy, although even he has been shown to get quite volatile when his brother's life is threatened.
- Spell My Name with an "S"/Adaptation Decay: In the credits and subtitles of the first film, he's listed as Conner MacManus. In the first movie's shooting script and the sequel, he's listed as Connor.
- Vigilante Man: He's more than willing to put the law into his own hands is it means saving other helping others.
- Vitriolic Best Buds: With his brother, Murphy. Even though the two are inseparable, they have been known to get into petty squabbles.
The more impulsive MacManus twin.
- Anti-Hero: He can be hotheaded at times, but he genuinely cares about helping other people by killing those who would do them harm.
- Berserk Button: Don't hurt his brother, or any of his friends.
- Deadpan Snarker: There aren't very many situations where Murphy doesn't have a quip ready.
- Foolish Sibling, Responsible Sibling: While both of them are fairly hot-headed, Murphy is definitely the more impulsive of the two.
- Hair-Trigger Temper: Compared to Connor, Murphy has more of a tendency to lose his shit and lash out when provoked.
- Jerk with a Heart of Gold: He's hot-headed, prone to swearing and a bit violent, but so long as you don't have the blood of the innocent on your hands, he's a pretty nice guy to hang out with.
- Knife Nut
- Pretty Boy: Come on. It's Norman Reedus.
- Red Oni, Blue Oni: Red to Connor's Blue.
- Smoking Is Cool: Smokes a lot more. Played almost literally in a deleted scene, where Murphy lights one up right before he takes a shower and promptly complains that Connor used up all the hot water. May also be inherited from their father.
- Tranquil Fury: When shit really hits the fan, Murphy tends to stay very calm while reacting.
- Would Hit a Girl: In his defense, the girl in question was bigger than him, and had just nailed Connor in the nuts.
Il Duce, aka Noah MacManus
- You must watch, dear. It'll all be over soon.
- All There in the Manual: The tie-in comic book expands on the backstory seen in the second movie.
- Archnemesis Dad: He's hired by Giuseppe Yakavetta to kill Connor and Murphy in exchange for his freedom. This is later subverted, however. Once he realizes that they're his sons, all bets are off and he helps them kill Yakavetta.
- Badass Beard: For the second movie.
- Badass Grandpa: He may have gray in his hair, but Il Duce is more dangerous than anyone can ever guess.
- Beard of Evil: For the first movie.
- Cigar Chomper: Word of God says they had to give Il Duce a smoking habit, because Billy Connolly couldn't stop smiling during the firefights.
- Cold Sniper
- Dual Wielding: Just like his sons.
- Eerie Pale-Skinned Brunette: When he was younger, at least.
- Everyone Has Standards: Il Duce is a merciless killer, but he refuses to kill women. This ends up saving Smecker's life when he arrives to Yakavetta's mansion in drag.
- HeelFace Turn: He's first hired by Giuseppe Yakavetta to hunt down and kill Connor and Murphy. Once he realizes that they're in fact his sons, he stops pursuing them and joins their crusade for justice by killing Yakavetta during his trial.
- Freudian Excuse: When Il Duce was younger, his father was murdered by mobsters before his eyes.
- Improvised Weapon: In the comic, he and Louie end up defending themselves with everything they can get their hands on in the leather shop. Louie's heavy metal leg brace even serves as a way to strangle a thug.
- I Was Quite a Looker: During his youth, Il Duce was quite the handsome young man.
- Knight of Cerebus: Whenever Il Duce gets called in around the halfway mark, things get serious. Which is very odd, seeing as Il Duce is played by Billy Connolly.
- Lennon Specs
- Long-Lost Relative: Turns out, he's actually Connor and Murphy's father.
- More Dakka: He wears a specially modified vest that holds six guns.
- Papa Wolf: Don't you ever try to hurt Connor and Murphy in front of him.
- Shipped in Shackles: Il Duce (who provides the page image for this trope) is introduced in the first film being moved from his cell to the ground floor for a parole hearing. He is cuffed hand and foot, chained to a rolling platform, and wheeled down to the parole board. The entire prison is put on high-alert, with shotgun-wielding guards on every floor, all to move one man down a few flights of stairs. Once he's there, they even put him inside a metal cage to protect the parole board. All of this serves to establish the guy as a hard-core badass.
- Throw-Away Guns: His signature gun vest. Justified, as it makes a seasoned FBI detective believe he was six men instead of one, making it harder for him to be traced.
Special Agent Paul Smecker
- There was a FIREFIGHT!
- Agent Peacock: Smecker proceeds, throughout the film, to become more and more camp and more and more awesome, culminating in the Wholesome Crossdresser-incident listed beneath.
- Awesome by Analysis: He shows this constantly, as he manages to piece together crime scenes with relative ease. He also does it so he can poke fun at Dolly, Duffy and Greenly.
- Badass Gay: He earns the title "Special Agent" for a damn good reason, has sex with other men, and hangs out at gay bars. Doesn't stop him from using derogatory slang towards them from time to time.
- Bunny-Ears Lawyer: When first introduced, he investigates a crime scene while listening to classical music on a set of earbuds, dancing along as he goes. He gets weirder as the unfolding events continue to wear on him.
- But Not Too Gay: Played with as Smecker is actually the most sexual of the main characters, but he doesn't cuddle and he seems annoyed with most gay men unless they are actually having the sex. After the sex, not so much.
- Deadpan Snarker: Mostly when working with Dolly, Duffy and Greenly.
- Friend on the Force: He starts to become this to the Saints over the course of the first movie, confessing in church that he believes in what they're doing.
- Groin Attack: Delivers five in a row to a mook.
- Jerk with a Heart of Gold: He constantly humiliates and one-ups detectives Dolly, Duffy and Greenly, and can be downright unpleasant at times, but he's an honest cop who wants to do the right thing. Even Duffy admits that while he was a pain to work with, Smecker was a "stand-up guy".
- Large Ham: Probably the biggest ham of the first movie, especially during that scene.
- N-Word Privileges: Averted, and Played for Laughs at the same time. He repeatedly calls other gay men homophobic slurs, and is unfailingly given dirty looks. At the very least, he doesn't seem to mind when it's directed at himself, either.
- Not So Stoic: While he's a little weird from his very first appearance, he is generally calm and collected. As the bodies begin to stack up, he becomes increasingly frayed, bordering on Sanity Slippage, leading to his quote above.
- Straight Gay: He appears to play up the Camp at times to poke fun at himself. And to discombobulated straight cops.
- Wholesome Crossdresser: He does this to infiltrate the Big Bad's mansion. It inadvertently ends up saving his life, since Il Duce mistakes him for a woman from behind and simply knocks him out.
- You, Get Me Coffee: Whenever Detective Greenly would say something stupid or mouth off, he would be dispatched to fetch coffee and bagels.
Special Agent Eunice Bloom
- I am so fucking smart, I make smart people feel like they are retarded.
- Action Girl: Bloom is smart and good with a gun. Even when she gets kidnapped by Jimmy, she manages to turn the tables on him and make him talk.
- Contrasting Sequel Main Character: For Smecker. While she at first seems like a Suspiciously Similar Substitute, there are enough differences between them for her to be her own character.
- Smecker listened to music when analyzing a crime scene, Bloom would actually use ear plugs to cancel out all noise around her.
- Smecker made it a hobby of chastising and humiliating Dolly, Duffy and Greenly, Bloom is more frustrated by them but doesn't give them that hard of a time
- Smecker is a Large Ham and Bloom is more soft-spoken and reserved.
- Cowboy Cop: Aside from working with a group of vigilante killers, Bloom goes as far as helping them tamper with a crime scene to make it look more like a shoot-out and less of a hit.
- Gun Twirling: While in the cowgirl outfit. It Makes Sense in Context. Sort of.
- Insistent Terminology: Special Agent Bloom. Justified, as "Special Agent" is a specific job title in the FBI.
- Inspector Javert: Subverted. At first, she seems to be on the trail to hunt down the Boondock Saints, which leads to Dolly, Duffy and Greenly to try and throw her off the track. Turns out she was only looking for them so she could become their new "Guardian Angel".
- Male Gaze: Troy Duffy got Julie Benz to be in his movie, and damn it all if he wasn't going to take full advantage of it for his male audience! To be fair, this was after plenty of shirtless and/or naked Irish twins.
- Ms. Fanservice: High stiletto heels, cowgirl outfits, shorts skirts, hair color changes. You name it, she most likely does it at some point in the movie. It's even lampshaded by Smecker when he remarks about the length of her skirt at his funeral.
- Precision F-Strike: Does her nickname for Special Agent John Kuntsler sound familiar to anyone?Kuntsler: So, how ya doin', Bloomy?
Bloom: Just fine, Kunty.
- With Due Respect: Lampshaded.Eunice: With all due respect... man, I hate it when people say that because it is inevitably followed by a disrespectful remark. Here let me give you an example: With all due respect, detective, this matter falls under whatever jurisdiction I fuckin' say it does.
Detectives Dolly, Duffy, and Greenly
- Badass Beard: Duffy grows one out in the sequel.
- Black Comedy Rape: Greenly fears the idea of them being subjected to Prison Rape if they're found out to be covering the Saints tracks.Greenly: "Calm down? Calm down? You know they're gonna throw us in the Hoag. We put half those deranged sex-freaks in there. I hope you guys like cock-sandwiches, because we'll be eating them for breakfast, lunch and dinner!
- Butt-Monkey: While all three of them are are constantly humiliated by Agent Smecker, Greenly just can't seem to catch a break.
- Distracted by the Sexy: Greenly is even more dimwitted than usual around Special Agent Bloom.
- Friend on the Force: By the sequel, all three of them are this for the Saints and willingly help them in taking down Yakavetta.
- Inspector Lestrade: A trio of them. During the first movie, they have a knack for taking all the details and coming to exactly the wrong conclusion. When they finally do gets something right, mostly Greenly ("They were bad guys. Now they're dead bad guys." and "What if it was one guy with six guns"), no one believes them because of how often they screw up.
- Invoked in the second movie, as they intentionally take all the details and come up with wrong conclusions, because they are trying to cover for the Twins, and themselves by association. Until they realize that Eunice Bloom is on their side and is just having fun toying with them.
- It Has Been an Honor: Greenly's last words to the Saints.
- Only Sane Man: Compared to Dolly and Greenly, Duffy seems to be the one who doesn't get the most shit thrown at him.
- Overly Long Last Name: If you're wondering why a South Boston detective has the imposing name of Dolly, it's because his actual last name is Dollapoppaskalious. This is lampshaded in the first movie when Smecker manages to pronounce it.Dolly: Holy shit. You're the first one that's ever got that.Smecker: What can I say? I'm an expert at Nameology.
- Sacrificial Lion: Greenly.
- Those Three Guys
- Wrong Genre Savvy: The reason they have such a hard time figuring out what happened is because they don't realize the men they are after learned everything they know from watching bad television. Every overdone action movie trope that never happens in real life happens to or is invoked by the Twins.
- Affectionate Nickname: "Fuck-ass", due to his Verbal Tic.
- Cool Old Guy: He's completely okay with letting the Saints, a pair of wanted murderers, stay at his place for the second movie. Even in the first one, he's egging them on as they trash his bar beating up Russian thugs.
- Hollywood Tourette's: Averted. While Doc does display coprolalia (foul language), he also has the stuttering and motor tics most Real Life Tourette's sufferers have.
- Mixed Metaphor: He keeps coming out with nonsense combinations like "people in glass houses sink ships". Rocko offers to buy him a phrase book after that one.
- Verbal Tic: FUCK! ASS! Justified in that he has Tourette's.
David Della Rocco
- As Himself: David Della Rocco.
- Butt-Monkey: Both from his fellow mob dudes, who call him "The Funny Man" and make him tell racist jokes, and from the MacManus brothers, who mess with him every so often and put him on "bitch detail" during their jobs. Not that he didn't deserve it. Remember the stripper? But in contrast to the mafia's decision to just get rid of him, Connor and Murphy go ballistic when Yakavetta murders him.
- Cluster F-Bomb: This scene.
- Crouching Moron, Hidden Badass: Yes, he can be a bit of an idiot, but he can still hold his own in a gunfight alongside the Saints.
- Dude, She's Like, in a Coma!: After another successful hit, Rocco feels up topless stripper who fainted during the shoot out. The brothers are quick to call him out for it.
- Fingore: Rocco loses a finger during the big shootout with Il Duce, which is used by Smecker to finally gain his lead on the brothers. Another finger gets shot off at point blank range with Papa Joe's .357 magnum, shortly before the mob boss decides to just kill him.
- Face Death with Dignity: When Guiseppe is ready to execute him, Rocco simply glares him down without struggling or freaking out.
- Large Ham: Best exemplified by this scene where every line of dialogue he delivers is AT THE TOP OF HIS LUNGS! Say what you will about the character, but he has some of the most entertainingly over-the-top lines in the movie.Rocco: SSSSSHYYYYYYUT your FAT ASS, Rayvie! I can't go down to the store and buy a pack of cigarettes without running into nine guys you FUCKED!
- Pants-Positive Safety
- Plucky Comic Relief: Given his status as Butt-Monkey, you can usually rely on him for comedy.
- Posthumous Character: His role in the sequel, where he's only featured in flashbacks and dream sequences.
- Redemption Equals Death: Spent his entire life working for the Mafia and passively witnessing all manner of evil deeds. He signs on with the Saints to help them kill off the evil Mafiosos and gets killed.
- Sir Swears-a-Lot: You'd have an easier time finding a scene where he isn't swearing.
- Sixth Ranger: Well, third, but he's a latecomer to the team.
- Token Good Teammate: Of Guiseppe's mob. He only works for the mob and is forced to watch heinous crime after heinous crime. Having had enough, Rocco makes a full HeelFace Turn, defecting to join the Saints and acting as their man on the inside.
- Ascended Fanboy: He already knows who the Saints are and seems pretty jazzed about meeting them, despite having a gun in his face half the time during their first meeting.
- Badass Boast: During his introduction scene."Never fight a Mexican, Pierre. Pound for pound, toughest motherfuckers on Earth. You know why? We like pain, Pierre. Think about it, man. Tabasco sauce? What kind of fucked-up people invent that shit?"
- Berserk Button: Downplayed as he doesn't exactly lose his shit, but still doesn't take too kindly to prejudice directed towards Mexicans, mostly due to being Mexican himself.
- Boisterous Bruiser: He's a pretty talented fighter and a lot of fun to be around.
- Establishing Character Moment: Romeo is introduced in a naval fighting ring against a guy who's over a head taller than him. With his hands cuffed behind his back. Romeo beats him in less than a few minutes.
- Large Ham: He can be pretty loud at times and full of himself.
- Lightning Bruiser: Romeo is tough, strong, and pretty light on his feet.
- Manly Tears: Rather prone to these.
- Patriotic Fervor: He's extremely proud of his Mexican roots and racist remarks towards his ethnicity are guaranteed to make him angry.
- Replacement Goldfish: For Rocco. He has enough personality and wit to make him into his own character, proving that this trope can be effective.
- Third-Person Person: He has his moments.
- "Well Done, Son!" Guy: An approving pat on the hand from his uncle and clear father figure results in Manly Tears from Romeo as he reflects on it later. Naturally, the brothers tease him for it.
Giuseppi "Papa Joe" Yakavetta
- Bald of Evil
- Big Bad: Ultimately becomes this in the first movie.
- Bilingual Bonus: As the leader of the Italian Mafia, he has a tendency to speak both Italian and English.
- Defiant to the End: When the Saints prepare to execute him during his trial, instead of begging for his life, his Famous Last Words are "Vaffanculo", which translates to "Fuck you." in Italian.
- The Don
- Hoist by His Own Petard: He's the one who wanted to bring in Il Duce, and ends up getting killed by him.
- Large Ham
- Oh, Crap!: He gets two, when he realizes Il Duce is still on his way after killing Rocco, and when the Saints burst in on his trial.
- Politically Incorrect Villain: When Rocco tells him a joke involving a black man, he very forcefully insists that Rocco call him a "nigger".
- Smug Snake: He thinks he's getting off scot-free during his trial.
- Used to Be a Sweet Kid: The tie-in comic shows him as a typical little kid crying after getting a shot.
- Beleaguered Childhood Friend: He and Noah were close friends, with Louie helping him kill off the Mafia. It's revealed he only did this to rise up the ranks of the Mafia himself.
- Big Bad: Of All Saints Day
- The Chessmaster: Was originally The Strategist for Noah before becoming this.
- The Farmer and the Viper: Louie uses the Scorpion and Frog fable variant to explain why he betrayed Noah after they had worked together for so many years. But he also ruminates that like the scorpion, he lost everything by his betrayal, because he was no longer useful to the Mafia.
- The Man Behind the Man: He's the one who had been giving instructions to Ottilio, having him assassint
- Nom de Guerre: The Roman.
- Only Known by Their Nickname: The Old Man or The Roman. Even his FBI file only has a first name: Louie.
- Wicked Cultured
- You Have Outlived Your Usefulness: His reason for setting up Noah. Unfortunately, without Noah, the mob didn't really need him.
- Kick the Dog: The first thing he does is to shoot a priest in his church, under Concezio's orders, all to get the Saints' attention. Concezio's capos and lieutenants are appalled at this.
- The Napoleon: His terminal case of short-man's disease ends up leaving plenty of evidence for the police that otherwise wouldn't have been there. Bloom even calls him Napoleon.
- Psycho for Hire: Is a direct reason as to why he was hired. Concezio knew that if he asked anyone else, they wouldn't do it.
- 0% Approval Rating: Not even his under bosses care much for him.
- Bad Boss: He breaks the jaw of one of his subordinates just because he corrected his pronunciation of a word. How he treats his underlings the rest of the time isn't a huge improvement.
- Big Bad Wannabe: He might've been the one who ordered the hit in an attempt to bring the Saints to America so he could have revenge, but the idea actually came from The Roman, who knew that the Saints would kill Concezio.
- In the Blood: When he realizes he is about to die, he has the same Famous Last Words as Papa Yakavetta did years before.
- Large Ham: Guess it runs in the family.
- Malaproper: God help you, if you correct him.
- Unwitting Pawn: He religiously followed the orders of the Roman, completely unaware that Louie was actually trying to bring the Saints and their father back so they could eliminate the Yakevetta family in revenge for casting him out.
- You Killed My Father: His primary motivation for ordering the hit on the priest is so he could bring the Saints to New York and avenge his father's death.