Perhaps the most interesting aspect of Kanye West’s career has been his relationship to Chicago. Born in Atlanta and raised in Oak Lawn, Illinois, Chicago was never so much a part of Kanye’s blood as it was a part of his marketing. The man who proudly proclaimed himself the first rapper with a Benz and a backpack aligned himself with Chicago’s conscious-rap past on his first album. On his second record, the influence was subsumed by the music; Kanye and West-side emcee Lupe Fiasco performed linguistic hopscotch over a sample of “Move On Up,” a track Curtis Mayfield recorded 40 years previously in Chicago. By his third album, the requisite “Chicago” track had turned into “Homecoming,” featuring the dude from Coldplay. The city became less a place, less about people. It became a talking point—something for which Kanye could yearn.

I thought about Yeezy the other day as I zipped along Watch Dogs’ strange recreation of Michigan Avenue, wondering where the Field Museum went, and also wondering why I had just climbed out of a gigantic spider-tank, and why I knew the man idling in front of me was transgender. I thought about Late Registration—partially because Mayfield’s “Move On Up” was playing on the radio, and partly because that album, like this game, represents a gargantuan, flawed achievement, an almost physical space where the talent is nearly in step with the ambition. At the time Kanye was the best producer in hip-hop, but he seemed to be eyeing something larger on the horizon, a music at once universal and personal. And so his bright poppy aesthetic dilated; in came indie composer Jon Brion, string sections, Adam Levine and a sound so big it scared Nas. Watch Dogs, too, wants to bring everything in; it wants to say serious things about technology and surveillance and have spider-tanks and have a personalized bio for every single NPC in the game. For Mayfield and West and the developers at Ubisoft, Chicago is rocketfuel.

That almighty ambition is Watch Dogs’ strength. The game is a sort of inverse of Grand Theft Auto 5: triumphant in ambition but faltering in execution. Nowhere is this more apparent than in those NPC bios, which can’t seem to decide if they’re funny or serious. This is why I know, when I gaze at a character on the street and a wireframe bio pops up next to him, that his name is Felix Spencer and he huffs paints when he’s not working at his dry cleaner job; I know that Sarah Glick, at 58 years old, is necking with a man 37 years her junior, a man who makes $71,500 annually and apparently consumes hallucinogenic mushrooms frequently enough that that is the single most salient fact about him. What sort of man is this? None, to be precise. The self-conscious quirkiness of these bios recalls the advertisements that the apartment rental website Domu has subjected Chicago residents to the past few years, in which purportedly “real” people smile at us from the sides of busses and cabs, each boiled down to facts like “PJ. Turquoise dealer. Chatroulette addict.” Everyone has a fun name and a fun job and a one-phrase bio; a city full of handsome young quirks, all pining for an apartment in Pilsen. We read about them as we are joylessly shuttled to our jobs.

Watch Dogs’ Chicago, full of MMORPG enthusiasts and insomniacs and night-school attendees, rings just as false. In their unrealness, their exaggeration, and their sprightly insistence upon a class of human that resolutely does not exist, the Domu ads and Watch Dogs form a sort of obverse reflection of the Tribune’s “Lost Friends” feature series, which also feature portraits accompanied by words. Only in “Lost Friends,” which was composed entirely by teenage journalists, the words look like these, from Kristin Brown: “I saw (my dad) lying on the ground. … I was angry because it was on TV. That was a personal moment we were not allowed to have.” Or they’re these words, from Michael Walton II: “Sometimes at a funeral you can’t even cry just because it seems like a funeral is every other day.” A few weekends ago in Chicago, 45 people were shot, 8 fatally; these numbers actually represent improvement over recent years, but the improvements are incremental, and unevenly distributed. President Obama called the 65 children killed by gun violence in 2012 “a Newtown every four months”; residents from throughout the city gleefully refer to it as “Chiraq.” This nihilism is both a rallying point for politicans and a source of romanticism in pop culture. As the city’s violence rose in the public consciousness, Kanye ditched the forward-thinking Common and co-opted the drill movement, a burly, meatheaded hip-hop pioneered by producer Young Chop and the ultraviolent emcee Chief Keef. (Keef’s catchphrase is a chirpy “Bang bang!”)

There is a lot of violence in the Chicago I prowl in Watch Dogs, too. The game’s guns have the thinness of, say, the first Mass Effect game, firing out little plasmoid blasts of hurt in a sort of tok tok tok fashion. But a click of the joystick reveals a super-power; I slow down time and rattle off bullets in righteous John Woo style, shredding the faces and torsos of cops and gang members alike. That tok tok adopts the righteous rhythm and bass-heavy thomp of a Young Chop beat. This game was never meant to be an outright shooter, but instead a patient, measured game of mass murder. One side quest has me hunting down the source of a rash of dead bodies, but as I step over the bodies of Darren Taws, a train technician, and a man whose name I didn’t catch, I wonder why the side-quest corpses matter. Why do their stories get to be told when so many other trails lead back only to me?

In the slow enactment of violence—first hacking into the security system, pinpointing the doomed men, toying with them electronically, then creeping through the shadows to thin out the numbers before, finally, unleashing full slow-mo explosion-filled hell—the game finds its surest footing. As a stealth game, it features Ubisoft’s famous friction-less sense of fun, a slickness and sense of grace in its murders that few other developers approach. To play this game well is to play it beautifully. Grim white protagonist Aidan is more human than any of the Assassins he’s modeled off of, more earthbound and fragile, but he still has a dancer’s sense of movement. His legs soar to his right as he hops an easy fence; his baton to an enemy’s knees is bookended by dramatic flicks. When he takes down enemies in stealth it is almost an annexation of the spaces they once inhabited. It is a geographic exertion of power that the level design accommodates with great delight.

In real life, that practice is called redlining, and it too is baked deep into the fault lines of Chicago, where, in the 1930s, a literal red line was drawn around black neighborhoods on insurance maps of the city. Those lines have shifted over the past century—projects have turned into condominiums, and destinations into slums—but the sense of two Chicagos, one white and safe, the other black and dangerous, remains. (The murder rate in Chicago’s most violent neighborhoods can be 80 times what it is in its least violent ones.) This practice of re-drawing, of restructuring a city’s geography to tell a chosen story, is repeated by Ubisoft, who carve the city into blobs of island but pretend that these zones are differentiated in economics only.

This desegregated utopia seems stitched together as if by the fond recollection of a child. The Willis Tower and the gorgeous arcing steel of the Pritzker Pavilion are lovingly recreated, but the city is dotted with geographic impossibilities. What are these mountains in the distance, looming like monsters beyond the city? (“Do you know this place?” I am asked at one point, standing on an imaginary island.) Move out of downtown and the city’s distinctive, rigid grid of streets, which Daniel Burnham reinstalled after the original city burnt to the ground, mutates into a network of lassoing, curlicueing roads through nondescript urban facades. All the better to enact a car chase through, of course, but the graffiti-clad warehouses of the Docks lack any real sense of place. A gauzy sun beats down the morning after a hard rain, casting a familiar blue and orange light across streets that do not exist, that loop from nowhere to a tourist attraction and back to nowhere. At least I can drive a car through the crowds at Navy Pier now.

The game’s structural centerpiece also uncomfortably straddles the real and the dreamed-up: a protracted mid-game assault on the Rossi-Fremont housing projects, which are based in name, shape and general sense of damnation on Chicago’s notorious Cabrini-Green units. These projects are traversed three times, first as a hacker, then as a stealth infiltrator, then as the rifle-wielding angel of death. It is an ascent into hell: collapsed ceilings form makeshift hallways to new floors; a man disdainfully tosses money at a prostitute after a blowjob; someone yells, to no one I can discern, “Boy! You ain’t about that life!” In my earpiece, my partner muses, “People lived here?” to which my grim white protagonist replies, “And died here.” In my final jaunt up the urban space, through strobing ladder wells and bullet-riddled hallways, I flip the butt of my shotgun into gang members’ stomachs and snipe them at close range. I toss bombs beneath their feet and detonate IEDs as they flock into the room. The chapter is called “By Any Means Necessary,” evoking the rhetoric of the human rights activist Malcolm X. I wonder if this is intentional.

I can’t decide. For all Watch Dogs‘ wonderful forward-thinking largesse—its very serious aesthetic concern with memory and surveillance and violence—it still thinks small. The plot confuses memes with jokes, confuses hoops with plot points, confuses Deadmau5 with cool. We move from person of interest to person of interest, as in a Raymond Chandler story, but unlike in a Chandler story no larger structure takes shape. We uncover only more hacking, more people of interest; jabs are taken at corruption but the corruption is only a type of information, a thing to hack. We hop up and down the ladder, from club to ghetto to skyscraper, but each setting is just a new set of boxes and cameras and targets. It is assumed that the setting will tell the story, but the city will not speak.

Because a city cannot. A city is an idea that speaks through the stories we tell about it. Chicago serves a different function every time Kanye mentions it, but at least he meets its gaze. If the Watch Dogs series ever learns to do the same, it could be the most purposeful open-world videogame ever made.

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At some point, the city in all its infinite vagaries just becomes too much, so I hotwire a truck and get out of dodge. I take the winding roads out of the city and into the serene wooded retreat of Pawnee. I swim through a lake in my trenchcoat and hat, parkour over a sedan, and eventually hop on a dirt bike to follow the road up to its end. A handful of people are hanging out around a fire there, so I take a read of them. David Grant, 50, with a fresh pack of smokes in his pocket, plays some blues licks on an acoustic guitar. Lena Marsalli, who makes six figures, tells David, “That’s the shit.” Jojo Shaftsbury, who the game tells me recently witnessed a stabbing, vibes serenely nearby.

Behind them is a small wooden structure leaning against a rocky outcropping. I try to clamber on top of the rocks but can’t make it, so I head around, down a ledge about six feet, toward the water. The sun is setting, and I can see, just behind the rocks, another faint orange glow. It lights the back of the rocks in this imaginary archipelago, and it’s impossible to reach. There’s someone over there, sitting by that fire, whose name I’ll never know. That’s a start.

Bottom image via urbanfeel