Artists and designers through the age have imposed their visions of the present and future on an always-changing New York.

The earliest known map of New Amsterdam — what’s now New York City — was made in 1660 by Dutch surveyor general Jacques Cortelyou. Called the Castello Plan, it pictured a cute little settlement of tree-lined blocks and farm plots. Three years after this plan was drafted, the British captured the colony from the Dutch. Around that time, an unknown mapmaker, probably in London, ripped off the Cortelyou Plan, creating a more colorful, embellished rendering of the city for James Duke of York, who later became King James I. This map (above), adorned with cupids, pictured lower Manhattan as a verdant waterfront paradise, conveniently located next to “Longe Isleland.”

Whoever this anonymous draftsperson was, they kicked off centuries’ worth of creative cartographic renderings of New York City. Artists have since created New York maps using everything from honeycomb to scratch-and-sniff stickers. In You Are Here: NYC: Mapping the Soul of the City, a new book from Princeton Architectural Press, Katharine Harmon compiles 200 such maps, spanning four centuries. They chart the endless ways that artists and designers have attempted to visualize an outsized metropolis on a manageable, human scale.

Over the years, as the city grew ever more crowded, artists’ maps of New York City grew less starry-eyed and idealistic, more satirical and dystopian. Here, a decade-by-decade sampling of artists’ maps of New York City from 1911 to today, selected from You Are Here.

1911: Henry Wellge, “Greatest New York”

Bird’s-eye views were a popular cartographic style in the early 20th century. In 1911, German-born map artist Henry Wellge created this color lithograph picturing an aerial view of “Greatest” (not just “Greater”) New York, before it was overtaken by skyscrapers.

1928: Mélanie Elisabeth Leonard: A Map of New York in the Air, or Super-Man-Hattan

This map of “Super-Man-Hattan” appeared before a decade before the arrival of Marvel Comics’ Superman. Its title was most likely a riff on Fredrich Neitzsche’s concept of the Ubermensch, made popular in the 1903 George Bernard Shaw play Man and Superman. In this art nouveau vision, a purple pterodactyl peers down at pre-Empire State Building cityscape. It’s inscribed with a poem that references the power-hungry Ubermensches: “Arrogant, the city’s beautiful head/Glows above the swirls of her georgette clouds./Below, stark hands grasp Success./Drab drays swank thro’ the mud:/Parks gleam greenly.” See if you can find the Hell Gate.

1933: E. Simms Campbell, A Night-Club Map of Harlem

The cartoonist Elmer Simms Campbell offers a window into Jazz Age New York with “A Night-Club Map of Harlem, ” which first appeared as a centerfold in Manhattan magazine in 1932. The pictorial map illustrates the ‘Hi De Ho’s of Cab Calloway at the Cotton Club; the best places to Lindy Hop and see the “World’s Greatest Tapdancer”; and the “actual size of Harlem’s national drink: A shorty of Gin.”

Campbell, a friend of Cab Calloway, was a regular at many spots pictured here. He was also “one of first commercially successful African-American cartoonists,” according to Rebecca Rego Barry. During his decades-long career, Campbell illustrated for the likes of Esquire, Cosmopolitan, The New Yorker, and Playboy. The original “Night-Club Map of Harlem” was acquired earlier this year by Yale’s Beinecke Rare Book & Manuscript Library.

1953-1955: Nils Hansell: Wonders of New York

This treasure hunt of a pictorial map packs 301 city sites into six square feet. It was as useful for tourists as it is pretty: Nils Hansell illustrates the venue where P.T. Barnum displayed a mermaid, where to play indoor Polo, where to visit Barker and Bubbles (seals at the zoo). Next to the wonder-filled Manhattan, he draws a mini-Manhattan with a minimalist subway map.

1969: Oscar Newman, Plan for an underground nuclear shelter

This conceptual design by New York architect and city planner Oscar Newman proposed a sci-fi-esque solution to creating more space in Manhattan. After learning that an atomic test in Nevada had produced a massive underground cavern, Newman suggested developers use nuclear explosions to create similar subterranean spaces under the city. They’d be equipped with air filters reaching to the streets above—as well as Coca-Cola ads.

“Manhattan could have half a dozen such atomic cities strung under the city proper,” Newman wrote in Esquire, alongside this drawing. “The real problem… in an underground city would be lack of view and fresh air, but consider its easy access to the surface and the fact that, even as things are, our air should be filtered and what most of us see from our windows is someone else’s wall.” Made as the city was entering its grimiest decade, the satirical map is a departure from the more idealistic designs of previous years.

1977: John Cage, 49 Waltzes for the Five Boroughs

When Rolling Stone relocated from San Francisco to New York in 1977, the magazine commissioned a work by John Cage. “He presented them with 49 triangles drawn on a Hagstrom map of the city,” writes Harmon in You Are Here. “Each triangle, or ‘waltz,’ had three coordinates, equalling a total of 14 sites where anyone, anytime, could listen to the ever-changing ambient sounds of the composition. The ‘score’ came later, when he released a list of 147 street addresses for ‘performers’ or ‘listeners’ or ‘record makers.'” It turns the city into a found performance/sound meditation site.

Plenty of artists, musicians, and city explorers have drawn inspiration from 49 Waltzes for the Five Boroughs. In 2012, for example, the New York Mycological Society, which Cage cofounded, created a performance of waltzes based on recordings made where its members discovered mushrooms.

1988: Stan Mack, Inside Tompkins Square Park

“Inside Tompkins Square Park” parodies Manhattan at the height of the crack epidemic, before gentrification turned the East Village into a tourist destination. It first appeared in cartoonist Stan Mack’s Village Voice column “Stan Mack’s Real Life Funnies.”

In the book, Mack explains the era this map illustrates best: “Together the squatters, the homeless, self-proclaimed anarchists, artists and musicians, the drug addled, and all manner of political radicals and local affordable housing activists were pushing back against the city’s attempts to turn the neighborhood over to real estate interests. It was a combustible mix, full of humanity, greed, righteous anger, opportunism, politics, official blindness, and violence. In time, the gentrifiers won, as they often do in New York, and the East Village has become a sanitized version of its former self: decay and grunge are fashion statement,s ethnic food shops advertise gluten-free-organic-locally-sourced ingredients, new glass-fronted apartment buildings incongruously shoulder their way between ancient tenement buildings, streams of NYU students and tourists flow this way and that, [and] Tompkins Park has traded live-in refrigerator boxes for strollers and kids’ playground equipment.”

1999: Jeff Woodbury, Ground Zero

Looked at in hindsight, Jeff Woodbury’s “Ground Zero” reads like an eerie premonition. Made in 1999, it consists of a dissected map with Columbus Circle at its center, radiating out in rings every fifteen miles. It was inspired in part by the 1962 novel Fail Safe, in which a bomb drops on the Empire State Building. (Woodbury had noted that New York is a common target in many fictional depictions of nuclear apocalypse.)

Two years later, while watching from his Brooklyn rooftop as the World Trade Center collapsed, “Woodbury thought about the shock waves soon to radiate from New York around the world,” Harmon writes.

2008: Rick Meyerowitz, The Meltropolis 2108

A few details in this post-climate-change-apocalypse vision of New York City seem particularly foreboding today: The “Trump Sump” is adjacent to “Monument to the Last Liberal,” and “Ivankaville” is just south of “Giuliani & Partners Island.” “Clintunisia,” meanwhile, has replaced Haiti, next to the Dominican Republic.

If you recognize the map’s style, perhaps it’s because cartoonist Rick Meyerowitz, along with Maira Kalman, co-created the famous New Yorker cover “New Yorkistan.”

2014: Hong Seon Jang, Type City

In New York-based artist Hong Seon Jang’s “Type City,” letters from a letterpress turn into buildings in a miniature Manhattan.