I really like 1001 Queen St West.
Yeah, you saw that one coming. Rimshot and all. Wockawockawocka.
Though...hmm. Mundane 50s brick modern-Georgian with a 70s pillbox up front, and a series of actually-quite-good-but-doomed-anyway 70s pavilions in the rear. (Someday, someone in the Concrete Toronto spirit is going to speak up for the 70s pavilions--surely, the most underrated extant Brutalism in Toronto, even if one has to overcome the stigma of their function or their destroyed predecessor to properly appreciate them. Now, advocating their *preservation*, at least in toto; that would be a stretch.**)
**and the funny thing is, they actually *don't* seem that "dysfunctional" or even "brutal", despite their aesthetic and function. If they'd served as college dorms rather than as a psychiatric institution, they probably *would* get their due as 70s heritage cult objects--especially considering how un-disfigured they've been over 30+ years.
It isn't exactly for "Boston City Hall" reasons that advocating their preservation would be a stretch--more that, all things considered, let's not jump the gun here...