King of Chicago
This is another one that’s edging the “IF” category, but is probably closer than others on this list. Thought about putting this in the Ye Olde Video Games thread, but I figured I might as well put it here.
King of Chicago takes place in that whole 1930s gangster era. Obviously by the title the place is Chicago.
The closest I could say the gameplay is to is a VN. Hell, might in be an early example of one, since the original version of the game was pure conversation based and didn’t have any arcade like sequences.
Generally your character get a selection of a few choices in conversations which then lead to what happens next. Sometime this might be more conversation, sometimes it leads to an arcade sequence, sometimes it even gets you outright killed.
So you play as Pinky Callahan and Al Capone has just gone to jail, so it’s time for a new mob boss to rise to power.
However, you’re not even the boss of the Northside Gang yet, so you have to plan on taking out the “Old Man” before you can take on Santucci (Southside Gang) who is the main enemy you’ll be going up against.
There’s a cast of characters that show up in the game, sometimes more than others. The main ones you’ll probably see the most are Ben, Bull and Peepers who are all members of the Northside gang.
As I’ve mentioned the first order of business is taking out the Old Man. This can be done a few ways. You can set things up to just outright shoot him or even bomb him. Bombing something is an arcade sequence which I never could get the hang of and typically if you fail it, you get killed in the process.
Shooting him leads to a minor sequence of you pulling out a gun and aiming it before he does that to you. This is another arcade sequence that pops up after conversations from time to time. Sometimes suddenly, so you need to pay attention and be quick. (Or again, you’ll get killed)
The third way is to convince him to just retire.
Failing to get rid of the old man in a timely manner (Keep putting it off for example) eventually leads events leading to confrontation anyway and probably not in your favor. You might even get a sequence where you get thrown into the river wearing cement shoes.
In any case, however you get rid of the Old Man, the game opens up a bit more. You then get a desk where you can click on various things. One of these is a picture of your girlfriend, another is a ledger where you’re hiring more men and doling out how much money various people get. And finally you even got a small map of territory where you can plot your next take overs. Again, these are arcade sequences usually in the form of a shoot out with gangsters running around on screen while you attempt to shoot them like you’re playing Duck Hunt or another one of those type of games. (You can do bombings if you want though)
The shoot outs are easier than the bombing, though if you get shot too many times, it’s a game over. Also occasionally a woman’s shadow will pop up in a window and if you accidentally shoot her, it’s another game over. Though not an immediate one. You get some conversations leading to your arrest and then eventual execution. You even get the option of choosing your last words before you get a sequence of getting zapped in the chair.
The ledger really doesn’t do too much, though you might want to just make sure you’re paying everyone enough since if you don’t you’ll eventually get Ben complaining that everyone is pissed that you’re stuffing yourself while everyone else goes hungry. Not correcting this won’t end well.
Of course it wouldn’t be a gangster game if Pinky didn’t have a girlfriend. In this case, it’s Lola who is the one on the picture. If you click on the pic, you’ll get a scene with those two talking to each other where you’ll get some choices. Interestingly, you can go an entire game without ever interacting with her directly.
In-between doing all that, you’ll get more conversation sequences with choices of what to say, some of which are just flavor and don’t actually impact anything, while others lead to other potential action sequences. There’s also other characters that pop up like Pinky’s mom, some kid that wants to be a gangster, the mayor, Pinky’s childhood friend that became a cop, etc.
So you win by taking out Santucci and this can be accomplished two ways that I know of. One is the direct way of taking over all the territory in action sequences and then finally shooting him in a showdown.
The second way involves Lola. If you actually focus on her sequences and things are good between you both, you’ll eventually get the option of having her set up Santucci and you pop in to take him out without bothering with all the territory stuff.
Apparently there is a third way to win the game, but I never did discover it. Maybe it’s getting Santucci thrown in jail by bribing the mayor with enough money or something.
Much like taking out the Old Man though, taking out Santucci is on a timer. If you stall too long (Like going through a lot of conversation scenes and never going for the last territory or failing to take it over a few times) you will eventually get confronted by Ben who says the gang has lost faith in you as a leader and it won’t end well for you. I don’t think there’s an option to retire like the Old Man did either, you either get shot by Ben or you kill Ben and then Peepers kills you. I believe you can get arrested as well.
And that’s about it. It plays fairly quickly so I definitely played through it multiple times.
Now this game is from 1986, so I doubt anyone here will be playing it anytime soon though I did hear there was an emulated version available on apps. This version is the Amiga one which is definitely the best looking of the bunch (And the one I had). The original ye olde 80s Macintosh one looks like a horror show since they used digital claymation for the characters, but this is the one that had the pure conversation choice before they added more arcade sequences for the other computer versions.
You can probably watch a youtube video of it if you’re not interested in hunting down ancient games to play. There’s probably a couple versions that explore most of the options available of it.