In 1965, New York City’s then-mayor Robert Wagner signed the Landmarks Law of New York City, which helped spur the metropolis’ budding preservationist movement. But that law doesn’t offer a blanket protection for historic structures; sometimes, there’s nothing that can be done for should-be-landmarked buildings. In the years before and after the law was signed, dozens of beloved places were torn down, whether because of inaction, rejection, or pure skullduggery; these are 15 of our favorite lost landmarks of New York City.

1. PENNSYLVANIA STATION

Demolished: 1963

It’s all but universally agreed that the destruction of McKim, Mead & White’s Beaux-Arts train station—originally built in 1910, and torn down in 1963 to make way for the construction of Madison Square Garden—was one of history's most regrettable crimes against architecture. Horrified New Yorkers railed against the plans to raze their beloved train depot, and its ultimate demise helped galvanize the city's preservation movement.

2. STEEPLECHASE PARK

Demolished: 1966

Donald isn’t the first Trump to leave his mark on New York City’s real estate landscape: Fred Trump, The Donald’s dad, built more than 20,000 houses in Queens and Brooklyn in his career. In 1965, he acquired Steeplechase Park, one of Coney Island’s last remaining grand amusement parks, with the intent of tearing it down and building“a modern Miami Beach high-rise.” The problem? The area was zoned for recreational, not residential, use. And the Landmarks Preservation Commission (LPC) hadn’t yet weighed in. That didn’t stop Trump: in 1966, he held a party celebrating the destruction of the park, even allegedly handing out bricks for people to throw. Trump never did build his high-rise—or anything at all; he eventually sold the land back to the city in 1969.

3. BROKAW MANSIONS

Demolished: 1965

Three lovely French Renaissance-style mansions once stood at the corner of 79th Street and Fifth Avenue. They were built for Isaac Brokaw, a clothing manufacturer, and his family, but later became the center of another building battle. After the loss of Penn Station, activists—including Ed Koch, who would become the mayor of New York in 1978—rallied in an attempt to save the historic homes, one of the few remnants of NYC’s former “Millionaire’s Row.” The buildings were torn down in 1965, but their destruction ultimately helped push the Landmarks Law through the New York City Council and on to be signed into law.

4. THE “OLD” METROPOLITAN OPERA HOUSE

Demolished: 1967

Before the Metropolitan Opera moved into its swank digs at Lincoln Center, the famed company’s home was a smaller building at 39th Street and Broadway. The old Met has the indignity of being one of the first buildings destroyed after the law went into effect: it was on the Landmarks Preservation Commission’s first shortlist of buildings to be landmarked, but didn’t get the votes. It was torn down in 1967.

5. SINGER BUILDING

Demolished: 1968

One of the city’s first skyscrapers also has the distinction of being the tallest building to ever be (willingly) demolished. The Singer Building, built in 1908 in the Financial District, was the headquarters for the sewing machine company and one of two buildings the company owned in New York City. The other, at Prince Street and Broadway, still stands, but the building at Manhattan’s tip was demolished in 1968, with One Liberty Plaza built in its place. And while its demolition is considered an architectural travesty nowadays, at the time very few fought for saving Singer—it was never even considered for Landmark designation.

6. THE LOLLIPOP BUILDING

Converted: 2002-2008

Now occupied by the Museum of Arts and Design, this stately building at the southwestern end of Columbus Circle was the focus of a lengthy preservation battle. When the Modernist structure originally opened in 1964, it wasn’t exactly beloved; The New York Times' architecture critic Ada Louise Huxtable called it “a die-cut Venetian palazzo on lollipops,” inadvertently giving the building its nickname. But when the museum’s plans to overhaul the building surfaced—the iconic lollipops would be removed, along with much of its façade—many were outraged, particularly at the LPC for choosing not to make the building a landmark. After a protracted legal battle, MAD was able to make its proposed changes, and the new-ish museum opened in 2008.

7. DAKOTA STABLES

Demolished: 2006

A sturdy brick building at the corner of 77th Street and Amsterdam Avenue once served as a stable for the wealthy folks who lived in the neighborhood. It was converted into a parking garage by the mid-20th century, and by 2006, the LPC was in the process of deciding whether it should become a landmark. But a mere four days before they were to decide, bits of the stables’ historic façade were removed, rendering its historic significance all but moot. A new condo building now stands in its place.

8. SUPERIOR INKS BUILDING

Demolished: 2007

This former warehouse on the Hudson River just missed landmark status. In 2006, the LPC voted to extend the Greenwich Village Historic District to encompass the far western edge of the neighborhood—but left this building off of the map. It was also never considered for landmark status on its own, and by 2010, a swank condo building (which would later become home to Hilary Swank and Marc Jacobs) stood in its place.

9. 5POINTZ AEROSOL ART CENTER

Demolished: 2013

For years, a hulking warehouse in Long Island City, Queens, acted as a mostly legal graffiti incubator, with aerosol artists from around the globe coming to tag the space. But in 2013, the building’s owner Jerry Wolkoff made good on a threat to tear down the space to make way for condo buildings. Despite the efforts of the 5Pointz artists to have the space named a landmark (their proposals were rejected by the LPC), the warehouse was first whitewashed in the middle of the night, then razed in 2014.

10. RIZZOLI BOOKSTORE

Demolished: 2014

Though publishing company Rizzoli New York had only occupied its flagship store on West 57th Street since 1985, the elegant, bi-level space felt like it had been around for much longer. When the building’s owners announced plans to demolish the shop and rebuild on the site, Rizzoli fans—including Manhattan borough president Gale Brewer—sprung into action. Unfortunately, the LPC rejected a bid to landmark the space, saying the interior wasn’t old enough and the exterior had lost much of its historic character. The shop closed in 2014, although its owners plan to open a new shop in NYC’s NoMad neighborhood.

11. DOMINO SUGAR REFINERY

Demolished: 2014

Call this a case of adaptive reuse: the old Domino Sugar Factory on the Brooklyn waterfront was declared a landmark in 2007, but was bought by Two Trees, a real-estate developer, in 2012. Their plan calls for preserving some of the original Domino factory—but not the iconic sign—and turning much of the site into apartments. As a last hurrah before the buildings came down, artist Kara Walker held an immersive exhibit, “A Subtlety,” in one of the large, decrepit warehouses.

12. KENTILE FLOORS SIGN

Demolished: 2014

Brooklyn’s Gowanus neighborhood had a beautiful icon in the Kentile Floors sign. Once an ad for a flooring company, in recent years the massive steel marker became a symbol of the borough’s industrial past. (Inevitably, it showed up on T-shirts and tote bags.) But after a half-century of looming over Gowanus Canal—and several rejections from the LPC to landmark it—in 2014 the owner of the building it stood upon took down the sign. But not all is lost: Kentile has been preserved by the Gowanus Alliance, a neighborhood advocacy group, which hopes to put it on display in the future.

13. CAFE EDISON

Closed: 2014

Here’s an odd case: this Midtown cafe closed in 2014, but the Edison Hotel, whose ground floor the restaurant occupied, isn’t coming down. The hotel’s owners asked the managers of the decades-old cafe to vacate to make room for a high-end restaurant and a restoration of the historic space, which once served as a classy ballroom. But because of Cafe Edison’s legacy—Neil Simon set one of his plays there, and it’s long been a favorite spot with the city’s theater elite—preservationists called on the LPC to preserve the space. Alas, it was not to be. In an interview with the New York Observer, LPC communications director Damaris Olivo said, “We can’t landmark a diner because it’s a diner, we can only landmark a building.”

14. 69 VANDERBILT AVENUE

Demolished: 2015

There are plenty of times when historic buildings aren’t saved because of greed, inertia, or a simple lack of interest. But sometimes, buildings aren’t saved because they’re just too decrepit, and this 19th-century wood-frame home on a corner near the Brooklyn Navy Yard falls into the latter category. In 2011, the neighborhood surrounding the house was landmarked as the Wallabout Historic District, but 69 Vanderbilt was rotting: its foundation was not secure, the windows were boarded up, and squatters had made their mark. In 2015, the city finally—and reluctantly—tore the building down.

15. P.S. 31, THE BRONX

Demolished: TBD

Much like 69 Vanderbilt, the problem with this Bronx building isn’t whether or not it’s historically important. The building, often called “the Castle on the Concourse” (Grand Concourse, that is), was designated a landmark by the LPC in 1986. The problem is that the building has steadily deteriorated over the years, with officials referring to it as a “public hazard.” Though no concrete demolition date has been set, there won’t be much left to take down: bits and pieces of the building have been falling off (or, in one case, were knocked off by Superstorm Sandy) since it closed in the 1990s.