In terms of the US...
1)
Chicago: to me it's the ultimate city skyline. Perfect layers, balance, distinctiveness, good peaks, nice mix of eras, etc.
2)
Los Angeles: it's not the biggest, but it has one of the more iconic skylines around and I appreciate the distinctive Po-Mo buildings that add a variety of colours and shapes, while there's still City Hall and a layer of Art Deco and some newer stuff to balance it out
3)
New York: I feel like this needs to at least be in the top 3 just for its sheer size and impressiveness, but it's not my favourite. Maybe I've seen it too much, I'm not sure. The Downtown Skyline feels very underwhelming because the buildings are just huddled together and don't stand out super well, except for WTC. And WTC being so much taller just makes it seem lopsided and makes the rest feel stubby by comparison. It probably needs another 2-5 distinctive (non-skinny please) skyscrapers above 300m to balance it better. The Midtown skyline is more interesting but it also feels very chaotic, unbalanced, and messy. It's more substantial but I also feel like there aren't really good angles of it for some reason. The skinny towers don't help.
4)
Seattle: not much to say other than Seattle to me is an exemplar of the imposing American-style CBD ringed by mid-low density neighbourhoods and winding freeways and it has some of my favourite skyscrapers (Rainier, Columbia, Smith)
5)
San Francisco: This skyline really rose in prominence for me after Salesforce, but it always held a special place for me due to TransAmerica, also love the bridges and hills to add dimensions to the CBD
6)
Pittsburgh: not a big skyline by any stretch, but very well done
7)
Philadelphia: very much a "glow up" from the 1970s and despite the predominance of newer towers, manages to have distinctive focal points unlike Toronto or Miami
8)
Portland: probably one of my more controversial ones as Portland's skyline doesn't really stick out in most people's minds compared with other big West Coast cities, but it has a nice eclectic mix of colours and, again, some of my favourite buildings (KOIN, the Big Pink, Wells Fargo, 1000 Broadway, etc)
9)
Detroit: Detroit's skyline is probably one I like more in theory than in practice. When you can get a view from inside the city, such as from the north looking south, it's easily in the top 5, because all those Art Deco era skyscrapers are prominent, but the most accessible views from around the river are so dominated by Ren Cen that it's sort of like the Downtown Manhattan issue
10)
Dallas: it's just a fun skyline, what can I say?
In terms of Canada...
1)
Toronto: hard to dispute such an king in skyscrapers, particularly considering how much its grown. I do lament the shrouding of the old bank towers from the lake view and lack of non-CN observation decks to take in the skyline from, say, Yorkville (besides expensive lounges). My main issue is that the more distinctive towers have been engulfed by Vancouverism, so it's just the CN Tower and endless nameless blue, but new proposals seem to upending that a bit.
https://www.flickr.com/photos/clementlo/52428087621/
2)
Montreal: almost as good as Toronto for me and although I don't like many of the new towers, they haven't engulfed the older 1960s-1990s towers (yet) and so Montreal's skyline remains very distinctive to me. Some of the new towers aren't bad, either, but I do love Sun Life, Gauchetiere, CIBC, PVM, Bourse, etc. Do wish they got rid of that height limit, though as it's starting to become a tall Ottawa in areas.
https://www.facebook.com/jfsavariaphotographe
3)
Calgary: my only gripe is that the city is too eager to build twin towers. They're fine in moderation but start to be distracting in their repetitiveness after a while. It's also perhaps the only Canadian skyline where the new major towers don't just turn into an anonymous blob. The Bow, Brookfield, and Telus compliment Bankers Hall and Suncor and there's a litany of interesting shapes and designs throughout the skyline. Impressive too for its size to have such a skyline.
https://calgary.skyrisecities.com/fo...8#post-1758354
4)
Edmonton: biggest change over the last decade, even with only a handful of big changes. Feels refreshed and modernized, while still complementing what existed from the 20th century, so avoiding a slip into Vancouverist tower development. The glass towers are just another layer, rather than *the* layer.
https://twitter.com/i/web/status/1574071543780741120
5)
Vancouver: not the hugest fan just because of how cookie cutter all the condos look, but it's not bad if they're off to the side and you get to see the old office towers around Burrard or the pre-war skyscrapers in the DTES (which are some of the best high-rises in Canada)
https://www.flickr.com/photos/aerojad/52334984558/
6)
Quebec City: small but classic and extremely well done
https://www.instagram.com/zeshelter/
The rest I don't find particularly interesting, though Winnipeg, Halifax, and Victoria have some charms.
Outside of North America...
1)
Shanghai
2)
Hong Kong
3)
London
4)
Moscow
5)
Melbourne
6)
Guangzhou
7)
Dubai
8)
Singapore
9)
Frankfurt
10)
Tokyo