The 12 ugliest buildings in NYC

These New York buildings give new meaning to the phrase urban blight

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New York, you're a goddamned gorgeous-looking city—most of the time. Millions flock to our city to gawk at such architectural wonders as the Empire State Building and Neo-Gothic cathedral St. Patrick’s. But let's be honest about some of the buildings that make up the classic New York City skyline: They're ugly. Outright hideous, in some cases: the naked mole rats of architecture. And sure, some constructions suffer from being built in the wrong time and wrong place, we get it. But does that make them any less of an eyesore? It does not. So then, take a deep breath and peruse our slideshow of the 12 ugliest New York buildings. Got a few you'd like to see added to the list? Tell us about it in the comments below.


  • Photograph: Laura Gallant

    New York by Gehry

    (8 Spruce St between between Gold and Nassau Sts)
    Frank Gehry’s rippling, residential behemoth reminds us of one of those hulking movie spacecraft that lands by planting itself into the earth and deploying robot arachnoid pods that harvest humans for nefarious extraterrestrial purposes. It sort of makes you think about the Wall Streeter who can afford to live here harvesting taxpayer-bailout money to cover for their screwups. Sorry, that was a terrible analogy. It doesn’t change the fact that both Wall Street and this building are hard to like.

  • Photograph: Laura Gallant

    Citicorp Center

    (601 Lexington Ave at 54th St)
    Currently one of the tallest buildings in New York City, the Citicorp Center was nearly undone in its infancy by a fairly significant design oversight. William LeMessurier’s plan called for the building to rest on four pillars, each positioned at the center of its side, rather than at the corners. Because the unorthodox design concept and some cost-cutting construction oversights, the 59-story tower proved particularly vulnerable to high winds. The structure was eventually reinforced, but not before a close call with Hurricane Ella in 1978. The crisis was averted, though this asymmetrical folly of glass and steel prompts the question: Was it?

  • Photograph: Laura Gallant

    Verizon Building

    (375 Pearl St at Madison St)
    You’d think all of those years Verizon spent charging exorbitant monthly fees for nonsmart phones that we’d leave in cabs or drop in bar toilets would give it enough financial leeway to stick its name on a building that doesn’t make us want to puke every time we look at it.

  • Photograph: Laura Gallant

    The Blue Tower

    (105 Norfolk Street)
    The Blue Tower was designed by Swiss deconstructivist architect Bernard Tschumi, (insert your own joke about deconstructing the building here) and you can find its 16 stories looming awkwardly over the Lower East Side. Writes Tschumi: “BLUE did not start with a theory or a formal gesture, but took the character of the site as its source, parlaying intricate zoning into angulated form, and form into a pixelated envelope.” Yep, that’s how we feel about it, too.

  • Photograph: Laura Gallant

    New York Times Building

    (620 Eighth Ave between 40th and 41st Sts)
    Like the new Yankee Stadium, the Renzo Piano–designed building was supposed to be a necessary housing upgrade for a hallowed New York institution. Instead, it’s basically a jungle gym. Both failed to capture the magic of their predecessors, and consequently the Bronx Bombers and the Gray Lady lost much of their mystique. But Yankee Stadium—superficially, at least—gives a nod to its tenants’ rich history. The new Times building, on the other hand, stands as a stark reminder of the print industry’s bleak future.

  • Photograph: Laura Gallant

    Sony Building

    (550 Madison Ave between 55th and 56th Sts)
    Philip Johnson’s Sony Building (formerly AT&T) defied modernist architectural convention when it was built in 1984. The “Chippendale” ornamental groove at the summit went against all accepted practice of the time (mostly pioneered by Johnson himself), and the building still stands as a classical (or postmodern, depending on how you look at it) screw-you to the surrounding city.

  • Photograph: Laura Gallant

    Museum of Arts & Design

    (2 Columbus Circle at Broadway)
    According to MAD’s website, “2 Columbus Circle’s design, accomplished in collaboration with architect Brad Cloepfil of Allied Works Architecture, weaves MAD into the social and cultural fabric of the newly revived Columbus Circle and its surrounding neighborhoods.” Columbus Circle must be a culturally and socially awkward place. We once saw Jeff Goldblum walking around Columbus Circle. He was tall and ungraceful-looking, but not nearly as much as this.

  • Photograph: Laura Gallant

    The Standard Hotel

    (848 Washington Street between West 13th and Little West 12th Streets)
    Standing 18-stories high, the Standard Hotel straddles the High Line walkway like a big industrial robot creature, a megalith in concrete and glass. Situated in the Meatpacking District's club hub, the Standard became notorious when it opened in 2009 for its occupants having sex in full public view—a fact referenced in the 2011 movie Shame, where Michael Fassbender’s sex addict character Brandon does the dirty against a window at the Standard with a prostitute. Okay, so maybe we’ll keep this one.

  • Photograph: Laura Gallant

    Trump Palace

    (200 E 69th St between Second and Third Aves)
    Donald Trump has long established himself as the tackiest real-estate developer—tackiest human, perhaps—to ever walk the earth. This high-rise condo is a fitting tribute to a man and his hair, what with its ugly middle and uglier top. Actually, this is probably one of the least offensive of Trump’s numerous affronts to good taste.

  • Photograph: Laura Gallant

    One Penn Plaza

    (1 Penn Plaza)
    The least aesthetically pleasing structure in one of the least aesthetically pleasing neighborhoods, One Penn Plaza is, by this measure, possibly the least attractive building in New York. Located near the New Yorker Hotel, a strange and mysterious venue that was home to pioneering Austrian scientist and eccentric Nikola Tesla in his reclusive later years, One Penn Plaza stands as a bland contrast with what was once a pretty exciting neighborhood. Tesla may have been a futurist, but One Penn Plaza goes beyond his most dire prognostications. We are just glad he’s not around to see it.

  • Photograph: Laura Gallant

    The Westin New York at Times Square

    (270 W 43th St at Eighth Ave)
    This monstrosity looks like it belongs somewhere along South Beach, catering to vacationing Colombian drug lords and the casino buddies of top Republican presidential donor Sheldon Adelson. Instead it’s parked a block from Port Authority, and fits into the neighborhood about as well as the M&M’s World down the way. The Westin is also a bit of an anachronism—it was built only in 2002, long after the area’s flashier drug-dealing element could’ve made use of its Vegas gangster opulence. 

  • Photograph: Laura Gallant

    305 West 16th Street


    Described by one staffer as “piggy”, the sharp edges of this brown metal-clad condo building (designed by SLCE Architects) look out of place among its elegant Chelsea neighbors. It was mooted at one point that the building might be used as employee housing for Google employees (Google’s New York HQ is across the street) but the deal supposedly fell through. Never mind, there’s still a 37-foot-tall, 5,800-pound steel-and-concrete daisy on the roof, purchased by one of the buildings developers after he saw it at a Burning Man festival. Ahem.

Photograph: Laura Gallant

New York by Gehry

(8 Spruce St between between Gold and Nassau Sts)
Frank Gehry’s rippling, residential behemoth reminds us of one of those hulking movie spacecraft that lands by planting itself into the earth and deploying robot arachnoid pods that harvest humans for nefarious extraterrestrial purposes. It sort of makes you think about the Wall Streeter who can afford to live here harvesting taxpayer-bailout money to cover for their screwups. Sorry, that was a terrible analogy. It doesn’t change the fact that both Wall Street and this building are hard to like.

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31 comments
TheRhinosHorn
TheRhinosHorn

How in the world did the five-theater-destroying Marriott Marquis Hotel NOT make this list?

E J
E J

To say that 8 Spruce is ugly is a joke. The building is very unique as it looks like it is melting from up close but glistening in the sun from afar. Totally un-cookie-cutter. CitiCorp Center epitomizes Italian minimalism making this a classic building in the NYC skyline. Its 45 degree sloped crown made a huge architectural statement denying the skyline of a spire or flattop cap. Back in 78' it was one of a handful of buildings that dominated the skyline. 550 Madison, the former Atlantic Bell corporate headquarters has that classic Chippendale crown and a beautiful lobby. 2 Columbus Circle is definitely weird, but what better way to house the museum of arts and design in a building that is avant-garde in its architecture.


If I had to make a list of ugly buildings I'd say Madison Square Garden which looks like a giant cesspool, 450 West 33rd, 3 Park Avenue, The AT&T Long Lines Building, 375 Pearl, 1250 Broadway and 4 New York Plaza should be included.

Jwelsh8
Jwelsh8

I am mixed about this list. There are certainly easy choices included -- Verizon Building, One Penn Plaza -- but I am bit shocked by the inclusion of the Times Building -- a building I quite love -- and even the Gehry building, even though I think it looks like a cheese grater. (I find his IAC building on the West Side Highway much less successful.)


I am surprised there was no mention made of the MetLife Building, which strikes such a discord with Grand Central. And my personal least favorite building, that orange brick, windowless and unwelcoming monstrosity at East 34th and Park Avenue, turned 45 degrees to the street.

Aimee B
Aimee B

This list is so full of crap that somebody's sewer pipes must be massively backed up! Citicorp got a lot of positive attention when it opened, not just because of its crown (Along with Astor Plaza of Times Square, it was one of the first to break with the flat roofed style that had become dominant), but also for its public spaces- unlike the plazas of many towers, this one was people friendly. Gehry's tower is creative and original, I love its undulating surfaces. The New York Times building is also striking and unique, its facade is interesting because it's so different from your average garden variety curtain wall. And I've got a soft spot a mile wide for One Penn Plaza- from one side, it's massive- broad shouldered and muscular. With nothing else of comparable height around it, it looks like it's staked out its territory and nothing messes with it. Its tenants also love the unobstructed views from all angles! But from the narrow sides, it's downright slender. One of my favorite viewing angles is from the steps of the nearby post office, where you can see the narrow and broad faces at once. Looking up at it like that, it looks like a classic International-styled monolith. Dark and Bad-ass. The only major changes I'd make would be to replace the mismatched panes of glass it's acquired over the years, and maybe close up the openings in the crown around the cooling towers (perhaps some kind of fine metal mesh that looks solid from a distance but still lets air circulate) so it looks a little less industrial up there. I actually did a pretty cool Halloween/Convention costume inspired by One Penn, it got lots of love from building staff, and I've won some awards for craftsmanship with it too!

brklynmind
brklynmind

Ridiculous - Gehry building is original,interesting and beautiful.  Verizon Building is ugly but is about to get alot better looking with the addition of windows on upper floors, Citicorp Center is another iconic building....This list is beyond stupid!

Anthony P
Anthony P

What about that godawful mess stuck on top of the Hearst Building at 8th & 56th? 

Ken B
Ken B

Def agree on the Blue Tower and disagree on the Gehry.  And they just CANNOT seem to get it right on Columbus Circle; the current bldg.: Feh which replaced the dreadful Huntington Hartford (?) white elephant that was there for years.  I do like the MAD though.  You would think that a museum dedicated to arts and design would have deserved a better home.

jasonacurry
jasonacurry

I love the Gehry Building, I'm looking at it right now from by window.  I do agree w/ the rest of the list.  I can also see the Verizon Building from my window—buuumer.  There are quite a few more Brutalist buildings around town that could be on this list...

Gene R
Gene R

Who the hell is this.. Drew Toal ?

I've never heard of him, do not agree with most of these and don't know what this jerks qualifications are.

Gene Robins

gener6935@yahoo.com  

GigiValenti
GigiValenti

The worst ever is 15 William St ... the yellow building which ruined the entire downtown skyline!

Jerry M
Jerry M

You left out the new New School building at 65 Fifth Ave and 14th street - just looks hideous and cheap!

chris s
chris s

Real New Yorkers hate these eyesores - across the board.  The hideous story-upon- story of undulating boring-ness, is only surpassed by their downright ugliness and lack of any sort of human scale.  Let the pumped-up, contemporary "size queen" architects feel good about themselves while receiving awards from their ilk. But In the meantime, Hunt, Gilbert, Van Alen, White and others who actually earned their creds as REAL architects in this city, are turning over in their graves.  Pathetic.  

Michael G
Michael G

New York by Gehry is amazing. It should not be on this list. I love Manhattan's classic "New York" style but it is so restricting for creative design in the future. This list does not count for me because BY FAR the ugliest building was left off the list. One Madison Park is the worst building ever to grace the New York skyline. It should be all 12!

ria
ria

whoever put this list together has zero understanding of either architecture OR ugliness.

Raymond
Raymond

I was beginning to think that I was the only person who thought this building was ugly. It's a pretentious eye-sore.

Jack
Jack

OK literally none of these with the exception of Citicorp Center are ugly. In fact, I would even call some of them masterpieces. I don't know what you think makes a building ugly, but I can tell you that your tastes go against the grain of the architecturally educated.

Kyle
Kyle

I love New York by Gehry! I think that building is fascinating to look at!

Joe Strike
Joe Strike

You picked a bunch of mediocre towers that aren't doing anyone any harm and overlooked the real crappy ones. Offender number 1: Cooper Union's recent building on 3rd Ave (Bowery?) between 6 and 7th street. Its facade features seasick-inducing curves and incredibly ugly gashes that looks like someone took a knife to the architect's model.

Matt
Matt

Luckily for the rest of the world, snotty & boring staffers at TONY have nothing to do with making buildings.

AUDREY M TORRES
AUDREY M TORRES

NOT LIKET TOWERS HIS OK HIS NICE THIS YEARS THAT FISCH TOWES GO THERE

A_
A_

I was surprised that Chase Bldg in Astor Place was not one of them. Seems like another ugly / unfitting bldg is about to appear across the street though.

Nelson
Nelson

Yes, Andy, Ghery is famous for the proliferation of his ugly buildings.

Lilly
Lilly

Tesla was from Yugoslavia! Born in Croatia. Check your facts before going on the web.

Andy
Andy

This list is already BS, based on the first building being there....Frank Gehry is only the most famous, prolific architect in the world.

Tommy T
Tommy T

@ria I agree! Some of these buildings are my faves in NYC.

Tommy T
Tommy T

@TJ Williams The pic you posted looks a lot like number two on this list. 

Robert Q
Robert Q

@Andy famous, prolific artist who designed a gross building, that obscures the Woolworth building, has a horrible industrial prison like school at the ground level, and has the potential to be dangerous any time there is wet heavy snowfall as the snow could accumulates and fall down the sides in the grooves