Cleveland: The Terminal Tower or the Rock ‘n’ Roll Hall of Fame.
Barcelona: Any of Gaudí’s works, probably Sagrada Familia.
Vienna: Either the Opera House or Hundertwasserhaus.
Paris: In addition to the Eiffel Tower, the Louvre’s Pyramid or the Centre Pompidou or Notre Dame.
Amsterdam: The Ann Frank House.
Venice: San Marco’s.
Rome: The Coloseum or St. Peter’s.
Marseille: Notre-Dame-de-la-Garde.
Toledo (Spain): The Alcázar or the Cathedral.
Florence: The Duomo.
I live in Vegas and I am not sure which building is the best fit.
I kinda want to say The Luxor.
Though Excalibur might be it.
Or it could be the New York New York. Which would be kinda odd…
Same thing with the Paris.
Slee
Is that the sharp pyramidal building downtown? googles Yep.
Until right this minute I had no idea what it was called, but many people recognize that particular “downtown view” are meaning “this TV show/movie” is set in San Francisco.
Barcelona, la Sagrada Familia or Camp Nou. Madrid, Cibeles, Plaza del Sol (more for the Spaniards) or Bernabeu. No, seriously, I’ve met many people whose reaction to “Spain” is “Barça! Real Madrrrid! Camp Nou! Bernabeu!” ok, ok, you can place Maracaná in a map, I heard ya.
Segovia, the Acueduct.
Pamplona isn’t known for a building so much as for a handful of streets and the races which take place thereof, but as buildings go the most emblematic is probably City Hall.
Madrid: I’d also include the Puerta de Alcalá. Not a building, but definitely an iconic structure.
Copenhagen probably has the smallest: The little mermaid. If that doesn’t count I guess Tivoli Gardens would be next on the list.
Well, it’s part of a building, it was supposed to be the Door in the walls on the road to Alcalá de Henares. The rest of the walls just didn’t get built, AFAIK.
Sydney has two iconic structures, the other being the Sydney Harbour Bridge. Does that make it easier?
I think of the big sign outside the Stardust with the “falling” lights. Or the Luxor.
Yes, but one is instantly recognizable to more or less everyone and one is not.
I don’t relate Orlando to the Magic Kingdom at all since it’s in Lake Buena Vista.
I used to think Orlando’s iconic area was Church Street Station but that area has gone down hill over the past decade. I guess now if I think of an iconic image of Orlando I think Lake Eola.
The “city” of Lake Buena Vista is entirely within the boundaries of Disney property. It’s not like it’s a real place - it has 11 households in total.
Chicago: The Sears Tower (I refuse to call it by its new name) and the Hancock building. Heck, how about the whole skyline as seen from the lake?
Los Angeles: Hollywood Sign or Capital Records
Fenway Park, specifically the scoreboard on the Green Monster.
Boston: The Zakim Bridge is the most dramatic, but Old North Church with the Paul Revere statue in front would be the most iconic.
Columbus: Ohio Stadium
NYC: Empire State Building
Pyongyang: The Ryugyong Hotel.
Montreal: Olympic Stadium
Ottawa: Houses of Parliament
Cleveland: Terminal Tower
Providence: The exterminating company on I-95 with the giant blue-painted statue of Nibbles Woodaway, the termite, on top
Lately, Winnipeg’s tourism boards et. al. seem to hype the new Esplanade Riel pedestrian bridge as a city symbol, ever since the darn thing went up, it seems to have taken on a “symbol of Winnipeg” tone - I’ve been living here for close to 30 years and I can’t think of a symbol that did the trick before, but this seems to fill the bill now.
A (rather nice) picture can be seen at Destination Winnipeg’s site.
Not the double-decker swimming pool in “My Winnipeg”? 
Boston - the Pru?
London - St. Paul’s?
Chicago - the Building formerly known as the Sears Tower?
Not the Riesenrad? That was the only Viennese structure I was familiar with before I went there.
Cape Town has the Castle, although it’s not nearly as well known as the Mountain, I think.
Cologne: the Dom.
Dresden: the Frauenkirche.
Prague: maybe Tyn Church?
Lisbon: the Torre de Belem.
Montreal: sadly, the Olympic Stadium. The mountain with the cross does nicely, too, but it isn’t a structure (at least the mountain isn’t).
Heh, haven’t seen (all of) Guy Maddin’s film yet, but, even though I’ve lived here 30 years now, I’m not familiar with that “sight” at all. Don’t get me wrong, knowing Guy Maddin and the film, I’m not the least bit surprised that he’d mention something like that, but I don’t think something like that has been around for decades.