The Weirdest Buildings of Lower Manhattan That You Need to See

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Welcome to Manhattan, or as Kurt Vonnegut calls it, “Skyscraper National Park.” He has a point: Manhattan is home to thousands of high-rise buildings in all shapes and sizes. Despite the island’s relatively small land mass, it seems like architects flock here to flex their creative muscles. Some of this flexing has resulted in instant NYC icons; others have resulted in instant confusion. Get ready to be confused because today we are going to check out some of the weirdest buildings in lower Manhattan. Don’t get me wrong: not all of these buildings are ugly, but they certainly are all odd.

The Oculus

It’s a bird! It’s a plane! It’s whale bones? Or maybe even the aftermath of a Thanksgiving turkey? Whatever you think it resembles, the Oculus is the most striking transportation hub in the whole city. It’s also the most expensive, costing the city nearly $4 billion to build. The hefty price tag may have been worth it because the Oculus is much more than a train station; it’s a swanky shopping center, a tourist magnet, and most of all a symbol of resilience. In the aftermath of 9/11, the station’s architect Santiago Calatrava aimed to create something that would be “a witness of belief that we can overcome this tragedy.” When you stand inside the Oculus and look up at the sky above, you get that inspiring feeling too.

56 Leonard Street

56 Leonard Street Weirdest Buildings in Manhattan

The designers of 56 Leonard Street describe this building as “a vertical glass expression of sculpted surfaces, cantilevers, and sparkling glass.” Anyone else would tell you that it looks like a tall stack of glass Jenga blocks. This thought has crossed so many New Yorkers’ minds, that if you google ‘jenga building,’ images of this building are the top search results. The designers certainly weren’t playing games when it came to amenities. 56 Leonard, which houses 57 floors of condominiums, has a 25-seat screening room, a private dining room, and a 75-foot infinity pool. You too can have a share of the Jenga Building’s fun and games if you have at least $2.3 million dollars to spare.

33 Thomas Street

33 Thomas Street Weirdest Buildings in Manhattan

Does something seem off about this building? It’s not a funky color or an unusual shape. It probably wouldn’t raise any alarms if you were just walking past it. But look closely. This brutalist building is missing a basic component: it has no windows. What type of building eschews windows? According to my research, 33 Thomas Street functions as a telephone switching center for AT&T, as well as a data center. Because it’s such a vital communication link, 33 Thomas is practically a fortress. It is capable of withstanding a nuclear explosion and fallout and it has its own gas, water, and energy supplies. I know where I want to be when disaster strikes.

IAC Building

Weirdest Buildings in Manhattan IAC Building

Anyone else getting nautical vibes? Architect Frank Gerhy took cues from his surroundings when designing this Hudson River-adjacent building, with the structure’s folds intended to mimic a ship’s sails. Inside, the InterActiveCorp (IAC) doesn’t sail the high seas, but they do surf the web. IAC serves as the parent company for websites like LendingTree,,, and

41 Cooper Square

41 Cooper Square Weirdest Buildings in Manhattan

The winner of the most controversial design on this list goes to 41 Cooper Square. When this structure was getting off the ground in the early 2000s, East Village residents protested its construction. They claimed that this addition to the Cooper Union campus didn’t fit the East Village aesthetics and would lead the way in converting the neighborhood into an extension of midtown Manhattan. While soulless high rises have yet to take over the East Village, the residents were right about 41 Cooper Square’s aesthetics. It looks like someone gashed the front of the building open with a giant ax.

Which building tops your list of the weirdest buildings in lower Manhattan? Let me know in the comment section! Check back next week for the weirdest buildings in upper Manhattan that you have to see! But while you’re here already, do me a favor and sign up for my email list and follow me on InstagramFacebook, and Pinterest. Your support means the world to me and allows me to keep sharing NYC’s culture, history, and things to do with you every week. Thanks for reading!


3 responses to “The Weirdest Buildings of Lower Manhattan That You Need to See”

  1. The Rockefellers' NYC: How One of Richest Families Made Their Mark on the City | Shiloh in the City

    […] success and power through the structure of his building. These days, the Standard Oil Building is far from the only imposing structure in lower Manhattan, but this beefed-up building still holds its own in the area, just as the Rockefeller family still […]

  2. The Weirdest Buildings in Midtown Manhattan | Shiloh in the City

    […] week we admired (or made fun of) Lower Manhattan’s weirdest buildings. Now we’re heading uptown to see the weirdest buildings Midtown has to […]

  3. oLaMothe Avatar

    Although the buildings may look weird to some people .I can’t help but, think that they have a certain Je ne sais quoi, that make them appealing.

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