Although China now has the most amount of skyscrapers in the world, the race to the sky began in America during the late 1800s, when architects decided that building out was so yesterday and building up was the future. These pioneering skyscrapers might look cute next to today’s supertalls, but back in their day, they were the equivalent of landing on the moon.
Each one held the title of world’s tallest building when completed, making them the original height-obsessed overachievers. From Chicago’s game-changing steel frames to New York’s Art Deco masterpieces, these buildings tell the story of how humans learned to defy gravity with style. Ready to meet the OG giants?
8. Chrysler Building, New York City (1930)
Although it’s not among the tallest skyscrapers in the USA today, it remains one of the most recognizable. This Art Deco beauty shot up to 1,046 feet, making it the world’s tallest for about eleven months before the Empire State Building crashed the party. The whole building is decorated with automotive-inspired details, from hubcap patterns to stylized radiator grilles and shiny eagle gargoyles that look like hood ornaments.
The lobby alone is worth the visit because, sadly, the observation deck is no longer open. But if we are being honest, the best views include the Chrysler Building, so head up the Empire State Building to catch the best glimpse.
7. Woolworth Building, New York City (1913)
Known as the “Cathedral of Commerce,” the Woolworth Building proved that five-and-dime stores could build monuments too. Standing 792 feet tall, this Gothic Revival stunner held the tallest title for seventeen years. The building’s terracotta-clad façade gives a nod to dramatic cathedrals, and you’ll even spot gargoyles, including one of architect Cass Gilbert holding a model of the building and another of Frank Woolworth counting his nickels and dimes.
The lobby is open during business hours and features Byzantine-style mosaics that’ll make you forget you’re in an office building. Today, the building houses offices and luxury condos, because apparently, living in a Gothic cathedral is totally normal in Manhattan.
6. Metropolitan Life Insurance Tower, NYC (1909)
Before Met Life was just another insurance company, they were showing off with a 700-foot tower modeled after Venice’s Campanile di San Marco. The building’s most distinctive feature is its four-faced clock, each face measuring 26.5 feet in diameter. The minute hands alone weigh half a ton each. At night, the tower lights up, serving as a beacon for lost tourists trying to find Madison Square Park.
While you can’t access the upper floors unless you work there, the ground level features some impressive marble work. The building underwent a major renovation that stripped away much of its original Renaissance Revival details, but the tower still stands as a reminder of when insurance companies had serious architectural ambitions.
5. Singer Building, New York City (1908)
Sadly, the Singer Building doesn’t exist anymore as this 612-foot beauty was demolished in 1968, making it the tallest building ever voluntarily destroyed. The Singer Building was the sewing machine company’s attempt to literally rise above the competition. With its distinctive mansard roof and elaborate Beaux-Arts styling, it looked like a French palace had a growth spurt. The building featured one of the city’s first high-speed elevator systems, whisking visitors up at the mind-blowing speed of 600 feet per minute.
Its demolition to make way for One Liberty Plaza remains one of New York’s biggest architectural losses. All that remains are photographs and the regret of city planners who probably should have thought twice about tearing down such an icon.
4. Flatiron Building, New York City (1902)
The Flatiron Building is by no means a skyscraper in today’s New York jungle and at 285 feet and 21 stories, it wasn’t the tallest when completed either. This wedge-shaped wonder was one of the city’s first steel-frame skyscrapers, though its Renaissance Revival facade makes it look like it could have been built centuries earlier.
The building’s unique shape created wind tunnels that allegedly blew up women’s skirts, making 23rd Street the original spot for New York’s street harassment problem. Today, the Flatiron remains one of the most photographed buildings in the world. The surrounding plaza offers perfect photo ops, and the neighborhood has evolved into one of Manhattan’s trendiest areas.
3. Prudential Building, Buffalo (1896)
Buffalo’s Prudential Building (now called Guaranty Building) proves that not all skyscraper innovation happened in Chicago and New York. This 145-foot Louis Sullivan masterpiece practically invented the modern office building aesthetic.
Sullivan’s famous principle “form follows function” is on full display here. Every surface is decorated, yet it all serves to emphasize the building’s vertical lines.
The building underwent a massive restoration in the 1980s that returned it to its original glory. Today, you can tour the lobby with its stunning mosaic floors and ornamental ironwork. Buffalo might not be on everyone’s travel radar, but this building alone makes it worth a detour.
2. Monadnock Building, Chicago (1891)
At 16 stories and 197 feet, it’s the world’s largest load-bearing brick building, stubbornly avoiding that newfangled steel-frame construction and the walls at the base are six feet thick! The building’s stark, unornamented facade was considered shockingly modern for its time, though it was really just the developer being cheap. Sometimes, penny-pinching creates accidental masterpieces.
Split between two sections built at different times, the building showcases the transition from old-school masonry to modern construction. The northern half is all brick, while the southern half cheats with a steel frame. Today, it houses offices and shops, and you can wander through to appreciate its canyon-like lobby.
1. Home Insurance Building, Chicago (1885)
The granddaddy of all skyscrapers, the Home Insurance Building, was a modest 138 feet tall when completed. Like the Singer Building, it’s no longer with us, demolished in 1931 to make way for an even taller building. Circle of skyscraper life.
This was the first building to use a full steel frame, making it the world’s first true skyscraper. The building’s steel skeleton supported the walls instead of the other way around, revolutionizing construction forever. While you can’t visit the building itself, a plaque at the corner of LaSalle and Adams marks where it stood. It’s a humble memorial to the building that started humanity’s vertical obsession. Without this Chicago pioneer, we’d all still be spreading out instead of up.
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