Ugliest New York buildings: Blights on the NYC skyline

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

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New York is world-renowned for its many architectural wonders, from the iconic Empire State Building to the neo-Gothic cathedral of St. Patrick’s. In fact, it’s difficult to step outside your door without running into some engineering marvel. But what about the misfires? Some NYC building projects suffer from being in the wrong time and wrong place, and others are just plain ugly. Here are ten New York buildings we could do without.


  • 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.

  • 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.

  • 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.

  • 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.

  • 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?

  • 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.

  • 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.

  • 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.

  • 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. 

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.

Users say

14 comments
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.