"It would be a mistake to discard any moment in history as useless or incapable of speaking to the present," says Kathryn VanArendonk. "That kind of disregard tends to be based on assumptions that could stand to be reexamined. But City on a Hill does not seem interested in unpacking elements of ’90s Boston in a way that feels any different from most other crime shows, nor is it uncovering a vision of Boston that felt in danger of being lost to pop cultural memory." She says the 1990s-set crime drama "doesn’t quite manage to sketch out the broad institutional framework that underpins a show like The Wire, and it also fails to make any of its primary characters especially endearing in a way that buys the show time for the rest of its mechanisms to click into place." She adds: "City on a Hill is oddly, unmistakably loving. It’s a depiction of rough-and-tumble Boston, a Boston of yesteryear, that feels distinctly nostalgic for the time of cash stacked inside holes in the wall and brotherly bands of men who knock over armored vehicles. And it’s hard to know of any other reason why City on a Hill is being made right now, except that it is a passion project by people drawn to that vision of the city — and here it’s worth noting that City on a Hill’s producers include Matt Damon and Ben Affleck, two men whose careers were shaped by writing and starring in Good Will Hunting, a movie also rooted in Boston’s working class. But for all of its bigness and lack of nuance, Good Will Hunting also casts a much more wary eye on the classist assumptions of Boston’s cultural divides. City on a Hill has no interest in that kind of analysis; its characters will never try to escape. It’s almost a fairy tale of a time gone by, when crime was committed by good working-class men, and corruption was sort of lovable. Or at the very least, when corruption coexisted with competence."
City on a Hill is the kind of show Seth Meyers would parody: "Three years ago, Seth Meyers skewered the proliferation of Beantown crime thrillers with a fake trailer for Boston Accent that nailed the tropes established in films like The Departed and The Town. That should have been a clear signal that future such projects would be well-served by putting a fresh spin on the material, but Meyers could cut together a sequel to Boston Accent using only clips from Showtime’s new series City On A Hill. It’s got everything short of a cop and his informant arguing whether to meet in Swampscott or Braintree… and that could happen yet."
City on a Hill is good if you like gritty crime drama and crooked cops: "The scope of City on a Hill is more ambitious than most of the Boston stories we’ve seen, including (Ben) Affleck’s The Town and Gone Baby Gone, and that gives it distinction," says Matthew Gilbert. "The show aims, through its many plotlines set in different corners of the city, to do what The Wire did in Baltimore — take a step back and look at how judicial, criminal, and political institutions work and, mostly, don’t work. No, City on a Hill is not nearly as sharp and authentic as David Simon’s masterpiece (The Wire) (even though Simon came up under (Barry) Levinson and (Tom) Fontana on Homicide: Life on the Streets); it’s showier, with sometimes-hammy acting, and far more melodrama. But, as its plots build and overlap, City on a Hill takes a more distanced, systemic view of this thorny city than expected."
City on a Hill starts from a rich premise and then it falters: "There are plenty of reasons that a relatively small U.S. city has become the staging-ground for crime stories onscreen from Mystic River to The Departed, says Daniel D'Addario. "Some are worthwhile (the city’s history of segregation makes it a dramatically interesting laboratory for ideas of justice), some less compelling (Boston accents sound funny to non-locals; a lot of creative people have roots there and are still hung up on it). Both sides of this equation come into play in City on a Hill."
City on a Hill isn't doing anything we haven't seen many times before, but it plays the hits well: "Creator Chuck MacLean loads up the scripts with pithy one-liners, the characters all have shady motives that keep you on your toes, and the supporting cast is stocked with familiar faces like Jill Hennessy, Kevin Dunn, and Sarah Shahi, who all do good work," says Liam Matthews. "And since it's a Showtime show, it feels built to last. The network likes to keep its dramas on the air for a long time, and City on the Hill has the kind of architecture that can support multiple subplots, new cases and characters coming up as other parts of the city get explored, and different combinations of characters as alliances shift."
In many ways, City on a Hill seems like a throwback drama -- if you have the time and patience: "The opportunity is there for Showtime, MacLean and company to really have something meaty to rip into for seasons to come. The trick, though, is circumventing that aforementioned attention-span issue — City on a Hill, early on, looks to be a series for viewers who are only committed to a handful of shows and can therefore give it their undivided attention, not the more plentiful modern group of viewers who are juggling 10 or more. Its density demands dedication."
Ben Affleck and Matt Damon need to get over their Boston obsession: "I say this as someone who loved The Town, Gone Baby Gone and The Departed—all movies that explored the Boston crime underworld, the crooked police force that aided and abetted, and the long-standing ramifications of their corrupt interactions," says Amy Amatangelo. "Showtime’s City on a Hill, which boasts both Affleck and Damon as executive producers, is so derivative of those three projects (you even can play six degrees of Kevin Bacon while you watch) that it’s laughable. I get why Affleck and Damon are so enamored with this particular slice of Boston history and lore; it’s fertile ground for a story. But you’ve had your fun and now it has to stop. While watching these first episodes, I could almost hear a Saturday Night Live parody of series."
City on a Hill gives Boston The Wire treatment: "Look out, David Simon, Chuck’s coming for you," Mike Hale says of City on a Hill creator Chuck MacLean. "Fair or not, The Wire and Baltimore are the obvious analogues for City on a Hill and Boston. And while the most noticeable names in the City on a Hill credits are the executive producers and Boston boosters Ben Affleck and Matt Damon, Showtime didn’t discourage any Baltimore associations by bringing in Barry Levinson and his Homicide: Life on the Streets partner Tom Fontana as fellow e.p.’s, with Fontana also serving as the City on a Hill showrunner. A conclusive comparison can’t be made because Showtime only provided three of the new show’s 10 episodes for review."