The story is styled after the so-called "poliziotteschi", the Italian crime movies of the 1970s that inspired Quentin Tarantino, as the creators proudly claim. You control Milanian hitman Piero Sacchi, who gets imprisoned for life at the start of the story, after he goes too far during a hit and wipes out his target's wife and child, which prompts a fellow gangster to rat him out to police.
Three years later, he's let out thanks to the boss of the Lanzetta family making a few well-placed contributions. Now, he expects the investment into Piero to pay off, since no-one else under his command seems capable of dealing with the ambitious rivals muscling in on the Lanzetta turf. And while he's busy doing wet jobs for Lanzetta, Piero himself is just as determined to find whichever rat set him up.
Milanoir features examples of the following tropes:
- Advancing Boss of Doom:
- At one point, you have a boss battle with a tram trying to run Piero over, while he's desperately trying to shoot the driver dead. Weirdly, the level just earlier featured multiple instances of trams crashing into the stationary trams unexpectedly present in their path, which kills the driver every time. That turn of events is highly unlikely for multiple reasons (from the mass of the tram dispersing the impact to the likelihood the driver would have had time to brake). It is even less likely when the tram the boss driver is in somehow protects him from multiple shots aimed directly at the cabin. Moreover, he actually crashes into multiple box barricades at ramming speed, clearing them out while taking no damage at all.
- The Metro boss battle also turns into this after it stops being a Dual Boss battle. If you end it by defeating Elena first (as you are likely to), she'll bow out by shooting the connector between the carriages. This means you'll no longer have her knife mooks come after you, but it also means there's nothing but gaping space at the end of the carriage. The remaining boss wields a submachine gun, too, from which you take cover behind a barricade of baggage. That baggage is effectively bulletproof...but it is knocked backwards a little by every burst from the boss, so that it is possible you'll get knocked off the whole train due to this if you take too long.
- Apathetic Citizens: During the "stealth" sequence on a market, several civilian bystanders pay zero attention to either the multiple criminal types patrolling the area, or to another shifty type in a red jacket periodically choking them out.
- Attack! Attack! Attack!:
- You may single-handedly put down about two dozen gangsters within just one level, but the remaining dozen is still going to be just as steadfast about trying to kill you.
- This is averted during your time in prison, however: when other prisoners ambush you with shivs in the yard, they stop blindly rushing at you once you find one yourself, and instead encircle you so that the best you can do is to is keep them away until the yard time runs out and the guards are forced to intervene, and you cannot actually kill any of them.
- Boss-Arena Idiocy: During the first battle with "Africana", she retreats behind a van whenever her health drops by a third, saying that she needs to catch her breath, and letting her thugs attack you on their own. However, there's a stop sign on either side of the van, and Piero's unique skill is to ricochet the bullets off of these. It's understandable that she had no idea Piero could do this the first time she goes behind the van: however, she goes to exact same place when she's down to the last third of her HP, rather than trying to hide elsewhere.
- Bottomless Magazines: Piero will never run out of bullets for his pistol, though he does need to reload it regularly. On the other hand, the other weapons you can occasionally pick up, like a shotgun or a revolver, are all much more powerful, but will get dumped for good as soon as they are out of ammo.
- But Thou Must!: The game railroads you into plenty of the villainous moments, like the time you first have to shoot Beretta's rattling locker by clicking during the cutscene, then you shoot Beretta himself during gameplay after it turns out that was a cat and he flips out (though you were going to shoot him anyway), and then you have to walk up to his grieving wife and cannot just leave, even though that's exactly what your partner Tony wants you to do, just so that you can trigger the cutscene where Piero stabs her to death as well.
- Camping a Crapper: In the opening scene, an assassin tries to pull this on Piero in a diner's toilet... but he makes a mistake and shoots dead the guy in the neighbouring stall instead. By the time he realizes his mistake, Piero already gets his gun out and shoots him through the door instead.
- Car Fu: More like motorboat fu, as you end the boss battle against the smuggler ship by revving up the engine so that it leaps through the air and lands right onto the top smuggler, instantly killing him.
- Cat Scare: When interrogating Gianni "Beretta", his locker starts rattling. Piero shoots, and you then discover it was their baby in there, as a bloodied teddy bear falls out. This provokes Gianni to draw his gun, and so you have to shoot him too, and then stab his widow as well. Though, Piero does ask who's in there and Gianni fails to respond. Then again, he might have thought he would have shot their child anyway.
- Concealment Equals Cover: Averted, in that many of the things you can take cover behind are not actually bulletproof, and will soon break apart under the sustained fire.
- Cool Shades: Piero always has these on. Torinese wears these too, to add to his role of The Lancer. Fittingly, Piero's shades get broken right at the point he finally manages to kill Torinese.
- Dark Action Girl: Africana and Elena both count, being powerful enforcers of their respective gangs.
- Death of a Child: The reason Piero is initially imprisoned for life, before his boss gets him out, is for killing the child of Gianni Beretta. This causes his partner-in-crime Tony to understandably decide he's too much of a lunatic, and rat him out to the police.
- Deliberately Monochrome:
- The close-ups of characters' faces during the conversations are done in black and white.
- Every time you kill someone with a revolver, the level briefly goes black and white.
- Destination Defenestration: The fate of Elena, right after she teams up with Piero.
- Diegetic Interface: There's no health bar; instead, the screen gets increasingly covered in film artefacts and even spaghetti stains as you take more damage. There's one instance where Piero does get a hugely visible health bar, however: it is when he gets beaten by the wardens in prison while already knocked to the ground, after they decide he hasn't been suffering enough for killing a baby. In that moment, he gets a health bar that goes across the whole screen, identical to that of the bosses.
- Disturbed Doves: Some levels have pigeons near distracted guards, which will take off once there's gunfire.
- Do Not Run with a Gun: The aiming reticle shakes if you try to aim while moving, and it shakes even more if you attempt to land a shot while running.
- Driven to Suicide: Piero's father hanged himself once Piero goes to prison and he found out he raised a hitman.
- Dual Boss: The battle on the train, against Elena and her unnamed black ally.
- Equal-Opportunity Evil: The rival gangs regularly have women backing up the men by trying to charge in with knives. Moreover, while most gangsters are obviously white, black or Arabic members are hardly uncommon, and the knife-wielding women can also be black or Asian.
- Even Bad Men Love Their Mamas: Heavily downplayed with Piero. When he's visited by his mother in prison, he knocks back her absolutely justified questions as to why he chose this life in spite of all their efforts with "I get slapped around by prisoners, I get beaten by cops, and now I have to listen to you moan?" and demands to get good food from the outside instead. Still, even his cynicism is breached once she tells him his father hanged himself from the shame of raising a killer, and he's rendered speechless in that moment. Later on, though, when wounded Ciero insults his mother, Piero drops any attempt at interrogating him and just finishes him off. Then again, Ciero likely knew that either he was too wounded to live anyway, or that Piero will kill him even if he spilled the beans regardless.
- Even Evil Has Standards: Piero's indiscriminate murder going beyond the moral code of a fellow gangster is the reason he ends up in prison in the first place. There, he's also reviled by the other inmates: after you grab your tray in the prison's canteen, every other prisoner whose table has a free seat tells you to go away. Later on, a couple of prisoners tell you they figured out a plan to escape and invite you to talk about it at the yard, when everyone will be watching football... only for it to turn out to be a trap, as they and another dozen of prisoners ambush you with shivs instead, and all you can do is to keep them away.
- Everything Fades: Even though the game prides itself on its violence and other transgressions, it still only takes a few seconds for the blood from the enemies' bodies to completely dry out and disappear. Similarly, spent cartridges drop out of guns, but will also fade away after a few seconds.
- Explosive Barrels: The docks level caps off with a battle against a smuggler ship which attacks Piero and his fellow thug by rolling such barrels off the deck and onto their motorboat, while you need to throw grenades right at that moment to blow the barrel on the deck, along with the person rolling it.
- Eyepatch of Power: Elena, a rival gang enforcer, wears one.
- Falling Chandelier of Doom: This function is served by the large cross in the Cathedral, which is dropped on Piero by Torinese shooting the rope holding it.
- Fate Worse than Death: Invoked on Piero's first day in the San Vittore prison. After he's knocked out in the canteen by another prisoner, the warden who attends to him summarizes the incident with "Welcome to San Vittore. Personally, I'm sorry you didn't die in custody. Soon, you will be too."
- Flunky Boss: Several bosses have back-up arrive at regular intervals, though it's usually in the form of basic guys with knives.
- Freudian Excuse: Averted. When Piero's mother visits him in prison, she explicitly says "We were good to you. We gave you everything. Why? Why did you do this to us?"
- The Guards Must Be Crazy:
- Enemies' awareness range is quite short, and so they won't react to Piero shooting dead fellow thugs if it occurs five meters away from them. Even if the thugs have the time to shoot back, they still won't alert the ones that are clearly standing within earshot.
- The docks level has motorboats regularly going through the channel dividing the level in two, and these all have a guy with a gun on them (as well as the untargetable driver.) Weirdly, you do not have to shoot them at all, as they will simply disappear after going offscreen: while they may not have enough room to turn the boat around, it's still strange that they won't even try to either stop the boat near the end of the screen to keep shooting at you, or to have the shooter climb up the bank to rejoin the fight.
- The stealth sequence immediately after that level will have several thugs patrolling a market and Piero having to choke them out one by one. The thugs can walk almost right up to a fellow criminal you just choked out, and pay absolutely no attention to him.
- Hand Cannon: The six-shooter revolver is very powerful, to the point its shots outright pierce their targets and continue on to the next ones.
- Mexican Standoff: One occurs at the end between Piero, Lancetta, and Tony. Ultimately, it doesn't get resolved: either Piero gets explicitly killed, or the game rolls the credits instead.
- Molotov Cocktail:
- Can be used by both Piero, and some of his opponents. Notably, they deal great damage and have a pretty large area-of-effect, although they cannot set other things on fire. Wooden objects hit by a Molotov simply break apart as if they got hit by a lot of bullets.
- Molotov cocktails also get all the big moments in cutscenes that the enemy bullets cannot. First, Piero has to jump off the smuggler's boat after a Molotov cocktail ignites spilt motor oil there on fire. Then, a single Molotov thrown off a scooter kills both of your allies during the park showdown, when earlier they had easily mown down the rival gangsters and were effectively immune.
- No Ending: In the end, there's a Mexican Standoff between Piero, Tony and Lanzetta. If you don't die there, the game just rolls the credits immediately.
- Only Known by Their Nickname: Piero's first assassination target in the game is only ever known as "Africana": not because she's African herself, but because she's into black girls, and so you begin the mission by attempting to ambush her at the brothel. You never find out just when the preferences of a high-ranking Mafia clan enforcer became such public knowledge.
- Over Penetration: Shots from the revolver can go right through several enemies at once.
- Pinball Projectile: It is possible to ricochet bullets off of street signs.
- Piranha Problem: When Piero is sent to deal with the madam controlling Milan's brothels, he finds out she's already made an acquaintance with a piranha tank. Notably, the game downplays the usual trope of piranhas stripping everything to the bone. Her body is still mostly intact, with only half an arm and a leg gone. Then again, there were only a few piranhas in that tank.
- Press Start to Game Over: Some levels begin with the enemies already aware of you and rushing your location, so one might die almost immediately.
- Recursive Ammo: An unusual example occurs with the triangular street signs. Piero is such a skilled hitman that he can shoot them at just the right angle to split the bullet in two. Moreover, the halved bullet will instantly kill both targets, whereas it usually takes 2-3 normal ones to do the job.
- Regenerating Health: Present so that you can recover health while in cover, though it doesn't happen very quickly.
- Rooftop Confrontation: There's one near the end, on top of the office block building, against helicopter from which you are shot at by Africana, who survived the hit you pulled on her in the opening. Then, the Mexican Standoff in the end also occurs on a rooftop.
- Searching the Stalls: A hitman sent after Piero tries to be Genre Savvy and just immediately shoots at the stalls. Unfortunately, that meant that he shot a wrong guy to death, while giving Piero enough time to pull out his own gun and shoot him the through the door.
- Shoot Out the Lock: You need to do this in the metro chapter to go through the metro train.
- Short-Range Shotgun: Played straight, as the hostile thugs with shotguns have to close in before using them, giving Piero a chance to shoot them from much further ahead..
- Shotguns Are Just Better: Averted. While enemy shotgunners are definitely more of a threat than the basic pistol or knife mooks, and are roughly even with the revolver ones, Molotov wielders are generally more of a threat, and they are absolutely no match for the Uzi users in the later chapters.
- Shout-Out: One of the chapters in the game is called "Almost Human", which is the English title for the 1974 poliziotteschi Milano odia: la polizia non-può sparare. Piero is also visually reminiscent of Tomas Milian's character in that movie, who was an equally ruthless and pitiless gangster. Several scenes (most notably the one with teddy bear) are also picked directly from this movie.
- Smoking Is Cool: Averted with Piero's smoking while in prison, as it is portrayed as desperate instead.
- Stealth-Based Mission: Several of these are present, and getting discovered immediately fails them.
- Tactical Suicide Boss: Torinese can only be targeted by Piero when he's under the streetlamps' light. Moreover, he understands that, as he'll regularly shoot out the light under which he got shot by Piero. Yet, he is not smart enough to either stay in the unlit areas where he's invincible, or to just shoot out all the lights after the first time he gets wounded, and remain invincible.
- Take Cover!: Even though it is a 2D game, cover is nevertheless very important due to the fragility of your character. However, enemies will often manage to land a shot regardless.
- Trap Is the Only Option: After the docks mission, the rival gang wants to call a truce, and so they set up a park meeting that'll supposedly be without guns. Piero immediately realizes that it sounds like a trap. Lanzetta simply replies that's why he'll be the one going there, as only he can be trusted to handle it anyway. It works out, as the other gangsters really did expect Lanzetta himself to show up in person.
- Universal Driver's License: Piero can drive a car, a scooter, a motorboat and a tram equally well.
- Unusable Enemy Equipment: Downplayed. The enemy equipment can be used... in the very rare, scripted circumstances when the game wants to have a setpiece opportunity.
- Vehicular Assault: There's both the first battle against Ciero, when he's trying to run you down with a tram, and a later battle where two minivans are both trying to run you down as well.
- Villain Protagonist: Piero is a wholly amoral gangster, and he remains that way throughout the narrative.
- We Have Reserves: The docks levels have motorboat riders spawn at set time intervals and indefinite number of times. Even the other levels usually feature some 20+ enemy gangsters in one spot at once per each setpiece. Even the chase against Africana's truck still has a dozen or so gangsters on scooters suddenly appear to back her up.
- What Happened to the Mouse?: Just who was stealing money from Lanzetta, if Piero was clearly broke the whole time? Can it really be Tony if Lanzetta doesn't even seem to consider that possibility?
- You All Look Familiar: There's usually one or two sprites for each enemy type. This is especially apparent when Piero is ambushed in the prison ward, as there are 14 enemies there, half with the exact same moustache and a beret, and half clean-shaved and with uncovered head. Moreover, the mustachio-ed and beret-wearing prisoners have a practically identical face to that of the pistol-wielding thugs at the docks in the next scene: only the clothing changes. Same happens for the other prisoner face type.
- You Kill It, You Bought It: Lucia claims that she wants to kill the madam who ran all of Milanese prostitution for revenge, but once she actually does it, she settles for taking over her position.
