The home of the World Series champion Red Sox opened in early 1912, and that makes it the oldest ballpark in all of Major League Baseball.

The arena, which seats just over 37,000, is also one of MLB’s smallest.

Because of this size and age, it’s also not as sleekly striking as its younger MLB brethren; positively dowdy, in short.

The Robert A.M. Stern-designed condo opened in 2009, and has rankled residents ever since for its starkly utilitarian appearance.

The 107-unit spire could be even more obtrusive, though, so points for that.

One Curbed Boston reader described this complex as "the world's largest air-conditioner."

Another brutalist punching bag, this monolithic structure went up in the late 1960s and very early 1970s.

Paul Rudolph designed it as a way to kind of exhibit government at work, but for many it reigns instead as an eyesore downtown.

The Catholic parish and charity hub is something to look at on the inside, but outside readers described it as basically monolithic and forbidding.

The building dates from the early 1950s—any later and it might've looked worse.

Boston's City Hall has been an architectural punching bag since its completion in 1968.

Kallmann, McKinnell & Knowles, then professors at Columbia, won an international competition to design the civic hub; and pivoted from more traditional fare as well as from sleek glassiness to a brutalist design that still perplexes and enrages the masses.

The Architects Collaborative was behind this 38-story skyscraper that went up in the early 1970s. It's another product of its time.

The pair of 40-story residential towers went up in the late 1960s and opened in 1971.

I.M. Pei designed them in the modern-slash-brutalist style popular at the time. They certainly stand out on the waterfront and not necessarily in a good way.