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The best buildings in Toronto since 1989?

- E.J. Pratt Library
- OCAD Sharp Centre for Design
- Sisters of St. Joseph Care Home Hospice
- Aga Khan Museum
- Blessed Pier Giorgio Frassati Catholic School
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Outside Core:
Terrance Donnelly Health Sciences Complex at U of T Mississauga - Kongats (masterful exterior)
Absolute Towers (instant classic)

Downtown Core:
Ryerson Image Arts/Image Centre - Diamond Schmitt (innovative adaptive re-use)
401 Richmond St W - Zeidler (innovative adaptive re-use, hugely influential)
20 Niagara St (hugely influential)
Graduate House, U of Toronto - Morphosis / Teeple

Not strictly speaking a building, perhaps, but also worthy of consideration:
Humber Bridge - Montgomery Sisam (foretold the redevelopment of the former motel strip)
Awesome endeavour, @AlexBozikovic. Very excited to read the book. Even just reading this thread and going through my mental catalogue of Toronto architecture has been moderately invigorating. It is also, I think, a reminder that we are privy to some really fantastic architecture despite the obvious (and well founded) griping about the general blandness brought about by the recent condo boom.

On the "since '89" front, unless I've missed prior mention of them in this thread, I'd add:
- Fort York Library
- Bergeron Centre for Engineering Excellence at York (I must just have missed this one in prior comments)
- Terrence Donnelly Health Sciences Complex (also might have been listed already; UTM and UTSC maybe deserve special shout-outs, perhaps as a part of the "outside the core" section? U of T has made a concerted effort and spent a considerable amount of money on its architecture, both inside and outside the core.)
- QRC West
- UTM Innovation Complex (Moriyama & Teshima)
- UTSC Environmental Science and Chemistry Building
- Tableau condos
- Ice condos
- Exhibit condos (obviously, iman-progress, but perhaps spawning another idea for a section of the book: awful condo names)
- Leslie Dan Faculty of Pharmacy building (especially at night)
- Terrence Donnelly Centre for Cellular and Biomolecular Research
- Parliament Street Data Centre (because even boring uses deserve beautiful architecture)
- MaRS Discovery District both for its magnificent indoor public space and for its adaptive reuse
- Humber Centre for Justice Leadership
- Waterfront wave decks

And on the age-agnostic, "outside the core" front, I'll add:
- R.C. Harris Water Treatment Plant. Visiting really just takes you a world (and a time period) away from Toronto, and it's a literally crucial part of Toronto's history.
- St. Augustine Seminary. Because that dome would look at home in Rome.
- Absolute World condos (apply to both categories, but potentially here in the vein of "see, the suburbs can do density, too, and it can be pretty as hell")
- Humber Bay arch bridge
- Technically not quite out of Yorkville, but I feel like we'd be remiss if not to mention the Toronto Reference Library
- Casa Loma (because how many North American cities have a castle downtown?)
- Brickworks (because the bricks that produced much of our vaunted single family homes came from here and ties nicely into an adaptive reuse thread)?
- Hearn (again, industrial past and adaptive reuse)?
- Royal Canadian Yacht Club island clubhouse (a vestige of Toronto's colonial past and a downright beautiful historical building)?
Walk 2:
Does it make sense between 3 & 4 to note the resurrected facade of the National Hotel as part of a new condo?
The Parliament Data Centre is deserving of a mention between an updated 8 and a completely rewritten 9: there's a whole other couple of pages worth to be discussed regarding 9.
The walk should also be extended east to cover the West Don Lands, especially River City, or add a new walk that starts in the WDL and crosses the Don into Riverside and Riverdale. (The revised book really should gaze at more of Toronto than just its navel. Cursory expansions into the outer areas of the 416 is a start, but there's so much more of the old city itself to add.)

Which buildings or landscapes best represent phases of the city's history and development?

I can't believe this hasn't specifically been mentioned yet, but the Distillery redevelopment is an obvious and hugely successful undertaking that almost singlehandedly pointed the way forward for the Pan-Am Games developments, the East Bayfront development and even the ongoing development of the King East design district. The whole area was little more than a post-industrial wasteland before the Distillery swung its doors open to the public like a phoenix spreading its wings.
Walk 1:
7b: note of the new courtyard between 7b and the condo to the north should be made, including the inlaid "stamps".
17: odd that there's no mention on Peter Dickinson, and you'll have to add a note about the L Tower.
I think it's also worth working The Esplanade and Market Street into the walk. Market Wharf's balconies when seen from various angles must be a point of interest for many, and that building is notable for nerdy reasons like that fact it was built with a basement so as to cap—not disturb—contaminated earth below it.

Golden. Thanks, Craig.
Certainly agree with a lot of the answers here- absolutely Absolute. More recently I'm also quite fond of Exhibit. Not strictly a building but the Calatrava's atrium is my favorite space in the Finance district, and I really like the Queen-Richmond centre- terrific job. On a similar note I'm looking forward to the proposed project on Atlantic Ave.
For the 905, UofT's Mississauga campus has some incredible examples of architecture in a pretty tranquil setting. It's not Absolute in terms of it's prominence, but definitely worth mentioning, and the campus itself makes for a great walk!

Perhaps the walk can involve a trip on the Mississauga Transitway? (The stations themselves are pretty neat) That takes you through the Airport Corporate Centre, the quintessential suburban business park, into City Centre (Absolute) - an example of how the burbs are trying to densify and create 'place', and then back onto the Transitway towards UTM.
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It is perhaps too early to say this, but Five condo demonstrated how to renovate heritage buildings on Yonge and keep that old small Toronto feeling while still adding big skyscrapers along a subway line. While the architecture is very nice, what it represents is/will be deeply relevant to the ongoing change to the city's main drag.
In Scarborough, you might consider including Raymond Moriyama's Momiji, the Japanese-Canadian retirement home. It was built with part of the reparation money for the treatment of the Japanese community in WWII, I understand. The exterior is pleasant, but the interior is a gem, IMO. The design and the quality of materials and the woodwork are superb. (Momiji means "maple" in Japanese so excellent woodwork is fitting.). The interior spaces exude serenity.

I tend to think good architecture is "inside out" for seniors' housing. The interior may take precedence.
Here are my additions, in case these haven't been mentioned already.

Best condos:
500 Wellington (architectural excellence)
MOZO (pioneering, mixed-use midrise)
18 Yorkville (pioneering tower-on-podium)
The Morgan (excellent historicist / Post-Modern architecture)
Radio City / National Ballet School (ground breaking mixed-use; architectural excellence)
River City 1, 2 and probably 3 (pioneering West Don Lands / Canary District project; architectural excellence)

Loft Conversions:
Candy Factory Lofts (pioneering project)
Merchandise Building (pioneering project)

Integral House (architectural excellence)

Gardiner Museum (architectural excellence)
Max Gluskin House (heritage preservation, extensive and possibly pioneering use of Core-Ten steel; architectural excellence)
National Ballet School (see Radio City above)
Royal Conservatory of Music (heritage preservation; architectural excellence)

Recreational / Community:
Regent Park Aquatic Centre (architectural excellence)
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Royal Canadian Yacht Club island clubhouse (a vestige of Toronto's colonial past and a downright beautiful historical building)?

Not exactly "colonial past"; the present Henry Sproatt clubhouse was built in 1906 and rebuilt after a fire in 1922. But mention should also be made of Laurence Cazaly's amazing late 50s RCYC bowstring bridge--an unsung precursor to the Calatrava/Humber Bay engineering aesthetic...
Brookfield Place. The tower facades topped with complimentary but varied spires are a scenic combination of postmodern and late modern geometry. The Galleria and banking areas/elevator lobbies are spectacular. The complex also nicely integrates the Hockey Hall of Fame into the old Bank of Montreal offices, as well as several other facades. It enhances the vista of the Gooderham flatiron building from Front Street with the skyscrapers in the background. In a district defined by midcentury modernism with buildings by Mies van der Rohe, I.M. Pei and Edward Stone, it holds its own as a spectacular landmark of its time. The city is better for it.