10 Ugliest NYC Buildings

We will take a bit of a break from mid-century buildings to look at some of the ugliest buildings in New York. Believe me, it took a lot to whittle the list down to 10. Here they are, in no particular order.

2 Columbus Circle

But since we are a mid-century site, we’ll begin with the destruction of a perfectly good building to “improve it” into this monstrosity.



Really, was there anything wrong with the original, affectionately known as the “lollipop building?”

Gallery of Contemporary Art, 2 Columbus Circle

Hearst Tower

Just a few steps from Columbus Circle is perhaps the most offensive building in town. The base of the Hearst Tower is a lovely art deco stone structure. Someone decided it would be a good idea to stick this fat, hulking mass through the middle of it.


8 Spruce St.

Speaking of ugly towers, this could be the worst in the city. It is marketed as “New York by Gehry” to honor the most overrated architect in the history of mankind.


IAC Building

Frank Gehry’s first attempt to ruin New York’s skyline was this squat, wavy building on West St.

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Don’t you love the way it intrudes on the sidewalk?

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In his defense, Gehry comes across as a decent guy in interviews. And he apparently has a sense of humor about himself, as he displayed in an episode of “The Simpsons.” I could only find the French version, but you’ll get the idea.

Whitney Museum

A few blocks down from Gehry’s disaster is another one by Renzo Piano. This guy designed a couple of mediocre buildings for the Los Angeles County Museum of Art. So the folks over at the Whitney asked him to do the same here. And he certainly delivered, coming up with a mish-mash of a building that gets uglier depending on what angle you view it.

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Blue Condominium

Another building that gets worse on each successive angle is the Blue Condominium on the Lower East Side. Real inventive name, guys.

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3 Park Ave

This thing sits like a fortress on 34th and Park. There used to be an armory on the site. Is that why they built such a blank, brick wall — as an homage?


Reebok Building

Well, that’s what we all called it in the neighborhood. Not only is this just an awful, awful building, it changed the entire complexion of Columbus Ave. And not for the better. I’ve still never figured out what that metal thing with the stakes sticking out of it is supposed to be. Art? It just always looked unfinished to me.



Here it is in all its glory in GIF form.


Westin Hotel

No comment on this piece of work.



Cooper Union

I know it’s an engineering school, but come on, did it have to commission this atrocity, perhaps the ugliest building in all of New York? Is there anything attractive about this building? It would work as a prison, maybe. Or maybe it is a lesson for its students on how not to design a building.

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The steel criss-cross beams make the sidewalk very welcoming, don’t you think?


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12 comments to “10 Ugliest NYC Buildings”
  1. Most of these are perfectly fine buildings that simply aren’t to your personal taste.

    Almost every building in the city fits that definition for someone.

  2. How could you not include 15 William Street fka William Beaver House? The yellow painted brick make it visible from pretty much everywhere and not in good way. The yellow looks like the building is unfinished, like exposed insulation panels.

  3. Hey K&A – the word “ugliest” suggests this is a matter of taste from the get-go. And this is a great list – these buildings are all ugly as sin.

  4. Your list is ridiculous. Grow up. You’re gonna list these statement buildings and not list buildings like the ATT Tower on 10th avenue? or buildings are legitimately are just gross like the budget hotels in midtown? This list just proves you don’t like contemporary structures, granted ugliness is subjective, but maybe if you sat down and attempted to apply some level of general objectivity you might have some credibility.

  5. This is the worst list I’ve ever seen in my life. The Cooper Union Building is one of the coolest buildings that exists, you simply don’t like contemporary architecture, you’re a fool. The housing projects that plague this city is what you should be really mentioning

  6. I don’t share your opinion. Some of them are great buildings. The IAC, Hearst Tower, Blue Condo to name a few.

  7. Why isn’t One 57 on this list?!?!?!?!? That building is so downright atrocious that Christian de Portzamparc should be banned from designing anything in NYC ever again. The multi-colored glass panels are an assault to the eye and a blight on the vista of Central Park. To think that the city’s NIMBYs continue to come out in force to block much nicer looking buildings and yet that awful eyesore was allowed to come to pass. What are those dreadful multi-colored glass panels meant to evoke???? The wall of a shower??????? By FAR the worst looking building in NYC!!!!!

  8. I have to agree with this list! Cooper Union tried to win our affections with a Happy Face, but it didn’t work! I have to admit some appeal in the Westin, but I even surprise myself! If these all fell to dust I would have to raise a glass to good fortune! To the eternal beauty of New York City!

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