Boston City Hall

Completed in 1968, Boston City Hall combines all the worst cliches of 1960s public architecture into one remarkably unattractive cast-concrete package. It even makes for an unfortunate metaphor for city government, since its cantilevered design means that the public sections of the building on the lower floors are dwarfed by the oversized upper floors housing the city's bureaucratic offices. A more pointed illustration of Boston's legendarily heavy-handed, obstructionist city politics is hard to imagine.

But what makes Boston City Hall a true monstrosity is the arid, treeless expanse of its surrounding red-brick plaza, which turns the once-thriving heart of downtown Boston into perhaps the most soulless and depressing public space in the country, of use only to the teenage skateboarders who get chased off its multi-leveled staircases on a near-hourly basis. Even during joyous celebrations like the 2004 Red Sox victory celebration, the plaza's overwhelming scale and dreadful monotony dampens any sense of human connection. Walking across City Hall Plaza on a cold, gray January day, when it turns into a wind tunnel that threatens frostbite for even the most well-bundled pedestrians, is such a hopelessly dreary experience it's a wonder Boston's suicide rate doesn't quadruple every winter.