At a glance: The King of Chicago · Apple IIGS · Cinemaware, 1989 · Gangster strategy adventure · Score: 7.5/10
Cinemaware’s second IIGS offering took the “interactive movie” idea somewhere Defender of the Crown never went: the back rooms and speakeasies of Prohibition Chicago, rendered as a living comic book of tough talk and tougher choices. The King of Chicago casts you as Pinky Callahan, a small-time hood with large ambitions in the vacuum left by Al Capone’s imprisonment. Starting with a tiny gang, a borrowed bankroll and a moll named Lola who has opinions, you have until the end of 1931 to take over the city — or to end up the way most of Pinky’s profession ended up.
The structure is a strategy game wearing an adventure’s clothes, and the clothes are superb. The campaign unfolds as a sequence of illustrated scenes — meetings, confrontations, negotiations, betrayals — in which dialogue choices carry real mechanical weight. Do you buy off the alderman or lean on him? Expand into a new district or consolidate? Trust your lieutenant, the memorably untrustworthy Ben, a little longer? Between scenes, a map-and-ledger layer tracks your territory, your gang’s size, your income from speakeasies and your standing with everyone from the mayor to your own mother. It is, in modern terms, a management game with a graphic novel for an interface.
Talk your way to the top
What still impresses is how much of the game is conversation. The King of Chicago’s cast — Lola, Ben, the rival bosses, the crooked officials — are drawn as archetypes and written with a pulp ear, and the dialogue trees remember what you have done. Generosity, menace and competence are all strategies, and the game grades your blend of them continuously: a Pinky who shoots every problem will find the city’s problems developing bodyguards. The branching is not infinite — this is 1980s software, and the seams show on a third playthrough — but a single campaign is full of moments where the “right” answer is genuinely debatable, which is more than most narrative games manage now.
The IIGS presentation serves the material handsomely. The game’s art style — flat-colour comic panels with heavy shadows — suits the super-hi-res screen beautifully, arguably better than the Amiga original’s more painterly approach: on the GS the panels have a crispness that reads like newsprint in the best way. Character portraits carry the acting, scene transitions keep the film-noir rhythm, and the Ensoniq chip supplies period-flavoured music and the occasional gunshot punctuation. Loading between scenes was the era’s tax; on modern storage the pacing snaps back to the brisk serial-adventure tempo the designers intended.
An empire in an evening — several evenings, ideally
A campaign runs a couple of hours, and the design expects you to play several. Pinky can die in a dozen authored ways, go broke, get frozen out politically, or — with the right blend of bribery, expansion and timely ruthlessness — end 1931 owning Chicago. The variables are visible enough to learn from: you can feel the difference a bigger gang, a fatter bankroll or a bought election makes, and failed runs teach the systems in a way that makes the victorious run satisfying rather than lucky. It helps that failure is usually funny. The King of Chicago writes its obituaries with relish.
A gangster epic you play by talking: The King of Chicago turned Cinemaware’s interactive movie into a pulp novel with a ledger, and the IIGS edition wears it beautifully.
The reservations are honest ones. The strategy layer is thinner than Defender of the Crown’s — territory maths is simple, and some scenes repeat across campaigns with only their outcomes changed. Players who want a pure strategy game will find a light one; players who want a pure adventure will find the management interruptions odd. But judged as what Cinemaware always intended — a film you steer — it is one of the studio’s most distinctive works, and the GS version is a first-class way to experience it.
The company it keeps
It helps to see The King of Chicago in Cinemaware’s IIGS pair. Defender of the Crown, its stablemate, is spectacle first and strategy second; King of Chicago inverts the recipe — conversation first, empire second — and between them the two games mapped the whole territory of what “interactive movie” could mean before the CD-ROM era claimed the phrase. Of the two, Chicago has aged the more interestingly, because its core pleasure — reading people, choosing tones, living with outcomes — is the pleasure modern narrative games rebuilt an industry on. Playing it now feels less like archaeology than like meeting an ancestor who resembles the grandchildren.
Practically, the modern player is well served: the game runs happily from modern storage, which removes the disc-swapping that once punctuated its scenes, and a campaign’s length makes it an ideal evening game — long enough for an empire, short enough for a rematch with a different strategy. Try the diplomat’s run after the gunman’s; the city, and Lola, will treat you very differently, and the second campaign is where the game’s writing really shows its range.
Lola, Ben, and the art of the cast
A word for the supporting cast, because they are the game’s real content. Lola — ambitious, clear-eyed, and entirely unwilling to be a hood’s ornament — functions as the campaign’s conscience and its scoreboard: her opinion of Pinky is the truest measure of his rise. Ben, the smiling lieutenant, is the game’s loaded gun on the mantelpiece, and how long you keep him close is the single most argued decision in the design. Around them orbits a Chicago of fixers, rivals and officials, each drawn in a dozen lines and voiced in fewer, each perfectly placed. Cinemaware’s films needed faces; on the IIGS, these are the faces, and they carry the picture.
The verdict
The King of Chicago is the thinking player’s Cinemaware game: an empire built from dialogue, bribery and nerve, illustrated like a pulp comic and staged with real flair on the IIGS. It is lighter as strategy than its reputation suggests and richer as storytelling than almost anything else on the machine. Take the city, Pinky. Just watch Ben.
For collectors, a closing note: the IIGS edition is among the scarcer Cinemaware releases for the platform, and its pulp box art makes it one of the shelf’s ornaments as well as its pleasures. For players, the simpler summary stands — this is the Cinemaware game for people who like their movies with dialogue worth choosing, and its Chicago remains open for business to any Pinky with the nerve to call on it. Mind the alderman, fund the speakeasies, and whatever Lola tells you about Ben, believe her the first time.
One more virtue deserves its line: restraint in the writing. For a game built on pulp, The King of Chicago knows when a scene is a look rather than a speech, and its best moments — a pause before an answer, Lola’s silence at the wrong moment — play like the films Cinemaware loved. The IIGS’s crisp panels serve that timing beautifully. Not bad for a gangster game you play with a mouse.
Score: 7.5/10 — Cinemaware’s gangster serial in a crisp IIGS presentation: build an empire one conversation, bribe and betrayal at a time.