Characters from the first game.
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Red mafia
Morreli
The boss of the Red mafia. He becomes Mission Control Tony is kidnapped.
- An Offer You Can't Refuse: He gives one to Vinnie, though it isn't presented as such. Vinnie finds out it's a rhetorical question a few seconds too late.
- Beard of Evil: He has one in the remake.
- Boom, Headshot!: Him and Tony are both executed this way.
- Cutscene Boss: Him and Tony are both fought and killed in a cinematic.
- Disc-One Final Boss: Him and Tony are killed rather quickly, with some police officers and the gray mafia boss being the last foes to be slain.
- The Don: Of the red mafia.
- Dual Boss: He's fought and killed alongside Tony.
- Even Evil Has Loved Ones: He loves his son Tony, and personally asks Vinnie to rescue him after he's kidnapped.
- Evil Old Folks: He's got wrinkles on his face, so this can be assumed. He's a mafia don and a ruthless man, so he fits the evil quota to a T.
- Faux Affably Evil: He seems pretty friendly for a mafia don, but quickly becomes ruthless when he feels insulted.
- Good Smoking, Evil Smoking: He's got a cigar in hand when Vinnie encounters him. When encountered again, he's smoking an even larger cigar.
- Mission Control: He becomes this after Tony is kidnapped by the gray mafia.
- Outliving One's Offspring: In the remake, Vinnie kills his son before him. Morreli only has about 5 seconds to mourn him before he's also killed.
- Papa Wolf: He makes sure that the best guy is sent to rescue His son Tony when he's kidnapped by the gray mafia.
- Related in the Adaptation: Tony is now his son in the remake.
- Resignations Not Accepted: Like Tony, he won't accept those who don't stay loyal to the red mafia.
- Too Dumb to Live: Trying to execute Vinnie was an absurdly stupid decision. While he probably wasn't as aware of Vinnie's skill with firearms as Tony, it was still a fatal miscalculation that led to his swift demise.
- Tranquil Fury: He's obviously pissed off at Vinnie for turning down a position in the mafia. So much so that he tries to have him killed right there.
Tony
Vinnie's boss and a mobster. He's second to Morreli, and serves as The Dragon for the family.
- Berserk Button: Don't try to leave the mafia. He'll quickly try to execute any defectors.
- Boom, Headshot!: Like many a character in the series, he's killed this way.
- Bullying a Dragon: He tries to execute Vinnie after seeing just how much of a One-Man Army the guy is.
- Cutscene Boss: Him and Morreli are dispatched in this way.
- Damsel in Distress: Him getting kidnapped drives the second act of the story.
- Deadpan Snarker: Like Vinnie, he's quite witty. He jokingly remarks that he wants to keep the chair he was held captive on.
- Dies Differently in Adaptation: He's stabbed through the arm in the remake, with the Boom, Headshot! being reserved for his father.
- Disc-One Final Boss: He's killed before the end of the game, with some unnamed police officers and the gray mafia boss being killed after him.
- The Dragon: He's the underboss to Morreli and a ruthless mobster who is a dangerous man when he's not being ambushed and kidnapped. He's the one to pull the gun on Vinnie when he rejects Morreli's offer.
- Dual Boss: Him and Morreli try to overpower Vinnie. It doesn't work, to put it mildly.
- Faux Affably Evil: He's quick to indulge in witty banter and comes across as a friendly man until he's angered. That's when his true colors slip through.
- Mission Control: He's this for Vinnie for the first few levels. He takes a pretty hands-off approach, just telling Vinnie to kill his targets and not cause too much of a mess.
- Noodle Incident: How the hell he was kidnapped so easily is a mystery for the ages.
- Related in the Adaptation: He's Morreli's son in the remake, possibly to give their connection more of an impact.
- Resignations Not Accepted: Vinnie finds out the hard way he's not allowed to leave the family alive.
- Too Dumb to Live: Pulling a gun on Vinnie sealed his fate, and showed how much of an imbecile he is, as he was well aware of just how dangerous Vinnie can be.
- Ungrateful Bastard: He tries to kill Vinnie for rejecting a position in the red mafia offered by Morreli even though Vinnie just rescued his ungrateful ass.
- What the Hell Is That Accent?: Supposedly Tony is an Italian mobster. His accent comes across more as someone aware of the regional differences who is unable to emulate them.
Gray mafia
Gray mafia boss (Edmondo)
The boss of the gray mafia.
- Boom, Headshot!: How he dies, like pretty much everyone in the game.
- The Don: Of the gray mafia.
- Even Evil Has Loved Ones: Unless he kidnapped them for a publicity shoot, he's shown posing in a photo with two children who seem to be related to him. They seem to be happy together.
- Fatal Family Photo: A framed photograph of him and his kids is displayed to the player before he's killed by Vinnie.
- Final Boss: Of the first game.
- Flat Character: Absolutely nothing is known about him apart from the fact he's the don of the gray mafia and he enjoys golf. The remake adds a bit of depth by showing that he has a family, though he's not saved from the Flat Character curse.
- Giant Space Flea from Nowhere: He has almost no bearing on the story and is never mentioned until the end, only being killed to stop him from coming after Vinnie for killing his men.
- He Knows Too Much: Vinnie kills him to prevent any retribution by the family for killing some of their members.
- No Name Given: He doesn't seem to have a name. Maybe Angelo stole it?
- Angelo presumably gave it back in the remake, where he's named Edmondo.
- Villains Out Shopping: He's golfing when he's assassinated.
Guy from the gray mafia
Some poor schmuck who was selling on the red mafia's turf.
- Asshole Victim: He is a mobster, so little sympathy is offered for his untimely demise.
- Boom, Headshot!: How Vinnie kills him.
- Briefcase Full of Money: He's carrying one. Vinnie, the greedy bastard that he is, decides to steal it as a compensation for his hit.
- Flat Character: He is in the gray mafia. He's presumably a low level mobster and arms dealer, but that's all that's known about him.
- No Name Given: He doesn't have a name. The briefcase he has is the only unique thing about him.
- Starter Villain: He's the first person killed in the series, though Vinnie has murdered far more people in the past.
Angelo
A mobster with a stupid hat who Vinnie interrogates.
- Ain't Too Proud to Beg: He's willing to plead for his life when cornered by Vinnie. It doesn't work.
- Bad Guy Bar: He's gambling with his fellow mobsters in some tacky and dimly lit tavern.
- Boom, Headshot!: He's untimately put down by a bullet to the head. This stops him from knowing that Vinnie stole his car shortly afterwards.
- Bullying a Dragon: Antagonising an armed mobster who murdered all your allies and threw a chair at you is a horrible idea. Vinnie isn't impressed with this bravado. In the remake, he drops this, and is far more rational and desperate.
- Cold-Blooded Torture: On the receiving end of it, from a pissed off Vinnie.
- Cruel and Unusual Death: He's maimed with several shots to the arm before being brutally executed. If he wasn't killed, he'd never be able to shoot with that hand again.
- Killed Offscreen: His bullet ridden body is the only indication of his demise in the original game. The remake lets you participate in his brutal death in all it's glory.
- Precision F-Strike: He curses at Vinnie when the latter has him looking down a handgun's barrel. He becomes a bit less cocky when he's tortured to death.
- Screw This, I'm Outta Here: He wisely tries to do this after Vinnie kills everyone by him. Cue a chair being chucked at his noggin.
- Sir Swears-a-Lot: In the remake, this is his coping mechanism as he's being shot multiple times.
- Too Dumb to Live: He continues to be a dick to Vinnie, even after being a witness to Vinnie's murderous methods. This goes as well as you'd expect. In the remake, he's more realistic, actually subverting this by pleading with Vinnie to spare him.
- Villains Want Mercy: In the remake, he pleads for his life as Vinnie starts shooting him. It doesn't work.
