Despite our best efforts, life—sometimes with the help of a wrecking ball—reminds us that nothing lasts forever, not even architecture that defines a location or cultural era. The 20th century saw the rise of buildings that reached iconic status for their impact on aesthetics, pop culture, and daily life, only to meet their untimely demolition, usually in favor of a more modern and arguably less-inspiring structure. Even the work of our most celebrated architects isn’t safe from destruction, like McKim, Mead & White’s Pennsylvania Station, Frank Lloyd Wright’s Imperial Hotel, or Richard Neutra’s Gettysburg Cyclorama. Here, AD has compiled a list of notable buildings from the 1900s that have been razed (and one that’s about to be), whose legacies, for better or worse, stand as a tacit acceptance of time.

The original Pennsylvania Station , the beloved bygone New York City landmark, was built in 1910 by the legendary firm McKim, Mead & White. Owned by Pennsylvania Railroad, the Beaux Arts building was demolished in 1963 because of a decline in railway ridership and replaced with Madison Square Garden and the current iteration of Penn Station.

A distinctive example of Brutalist architecture, the Prentice Women’s Hospital and Maternity Center in Chicago was designed by Bertrand Goldberg and completed in 1975. The building was razed in 2013 after its owner, Northwestern University, argued it needed the site to accommodate medical research facilities.

The Visitor Center at the Gettysburg National Military Park , better known as the Gettysburg Cyclorama , was designed by Richard Neutra and housed a 360-degree painting by Paul Philippoteaux of the Civil War battle Pickett’s Charge. The modernist structure opened in 1962, and despite protest was demolished by the National Parks Service in 2013 to preserve the historical context of the site.

Completed in 1906, the Marlborough-Blenheim Hotel was a destination resort hotel that graced the shoreline of Atlantic City, New Jersey. Designed by Will Price, the grand structure was featured in multiple movies, including Gary Marshall’s Beaches, and once hosted Winston Churchill. In 1978, the historic structure was demolished to make way for a casino.

After demolishing the original Savoy Hotel, Harry S. Black, then owner of the Plaza Hotel, used the site to build the Savoy-Plaza Hotel , which opened in 1927. The McKim, Mead & White–designed building was an iconic structure along the edge of New York City’s Central Park until its demolition in 1965, making way for the General Motors Building.

In 1919, Russian actress Alla Nazimova bought Hayvenhurst , an estate built in 1913 on Hollywood’s Sunset Boulevard. By 1927, she had added villas around the main house and opened the property as the Garden of Alla Hotel, and in 1930, new owners renamed the property as Garden of Allah. Before it was razed to make room for a bank in 1959, the hotel was a legendary Hollywood hangout, hosting guests like F. Scott Fitzgerald, Greta Garbo, and Frank Sinatra.

The Brown Derby restaurant, also known as the Little Hat, opened on Wilshire Boulevard in 1926 across the street from the celeb-studded Cocoanut Grove at the Ambassador Hotel. The eatery, still an icon of the city’s architectural history, was demolished in 1980 and turned into a parking lot.

Replacing Tokyo’s original Imperial Hotel after it was destroyed by a fire, Frank Lloyd Wright’s iteration of the building opened in 1923 in his signature Mayan Revival style architecture. And though it famously survived that year’s earthquake virtually unscathed, the iconic destination did not survive the test of time. It was demolished in 1967 to make way for the high-rise third iteration of the hotel.

Designed by Michael Blampied and opened in 1971, the Welbeck Street Car Park was a department store parking garage before its closure in March 2017. An icon of Brutalist architecture thanks to its honeycomb-like concrete façade, the building is currently scheduled to be demolished and replaced with a 10-story hotel.