Iconic New Yorker Covers that Address Politics and Culture

On February 21, 1925, the weekly magazine The New Yorker was published for the first time.

Since its founding, in 1925, The New Yorker has evolved from a Manhattan-centric comic paper to a multi-platform publication known worldwide for its in-depth long form reporting, both political and cultural commentary, fiction pieces, poetry, and most of all its renowned humor.

Most magazines use their covers to advertise a particular story within the issue, but with the  New Yorker centennial timeline being celebrated this week, the magazine uses its often-jokey covers to promote a not-so-generic sensibility.

From the magazine’s first cover, to a Hasidic man kissing a black woman amidst racial tensions in Brooklyn’s Crown Heights, the magazine’s cover has crystallized both the news and something more ineffable within the culture of story telling and reporting. 

Some of the most iconic New Yorker magazine covers history and these illustrations and works of art are the ones that address tragedy, or illustrate some kind of upheaval—political, environmental, social—that affected New Yorkers and other people of the earth on a larger scale.

Here is a list of some of the controversial New Yorker covers explained with a little bit of context.

It’s 1925 — the Jazz Age — and young journalist wants to launch a new humor magazine‬ focused on the city’s nightlife. The then art editor for this same magazine, Rea Irvin sets about to represent an urban sophisticate. In the encyclopedia, they find a picture of a Regency dandy, an 1834 engraving of the Count‬‭ d’Orsay. So for the first cover, Irvin, with a gentle self-mocking irony, has a dandy , Eustace Tilley training‬ his monocle on a fluttering butterfly.

Speaking of iconic maps of New York City on New Yorker covers—who could forget New Yorkistan. The story behind the humorous cover is of  2001 when the people of New York had settled into a deep funk, and the war against the Taliban had begun in Afghanistan. While the afghans were being bombed by the US, the news was bombarding with strange names: Pukhtuns and Pashtuns; Tajiks and Turkomen; Uzbeks and Baluchis; Khandihar: Khunduz; Jalalabad; That is when the artist came up with New Yorkistan and the editors loved it! We are glad they did!

The Cover is a testament to the emotional weight that overtook New Yorkers amidst the disastrous 9/11 attack.
“I‬ felt that the only appropriate solution would be to publish no cover image at all — an‬ all-black cover” says the then art editor Mouly, who along with the artist drew a twin dark tower to represent the emotional turmoil of the event. The cover went on the capture the evasive feelings of millions, while correctly depicting the depth of the twin tower attacks.

For the March 3, 2025, cover, Barry Blitt depicts Alexander Hamilton, Benjamin Franklin, and James Madison ejected from their offices—a startling representation of the chaos and mass layoffs of federal workers that have engulfed America since Donald J. Trump took office for the second time, writes The New Yorker.

In another such iconic image depicting the political mis-happening of the American world, Barry Blitt gives his take on the worldwide billionaire Elon Musk. “On January 20, 2025, the next leader of the United States—and of the free world—assumes power,” Blitt said. “Also on that day: Donald Trump is sworn in.” Says Blitt.

This New Yorker cover aimed to represent the Deepwater Horizon disaster. The Deepwater Horizon disaster occurred on April 20, 2010, when an offshore drilling rig exploded in the Gulf of Mexico, causing the worst oil spill in U.S. history. The blowout released millions of barrels of oil, devastating marine life and ecosystems. BP, the operator, faced massive fines and lawsuits. Artist, Bob Stake visualised the tragedy for the readers with the help of turtles and fishes jumping into the sky for refuge.

In this cover, the mother in pink arrives at a‬ playground to find only fathers there. The cover artists composition is built around a circle, children‬ and fathers revolving around it. The yellow slides function like arrows to make our eye‬ travel around the image. Everyone is in motion, in the middle of a movement, except for‬ Mom, where your eye comes back to rest. Is it a celebration or a introspection, that is left to the reader.

In another such cover for Mother’s Day, the New Yorker gives us a steaming glance of the mother itself. In the history of New Yorker covers,” Liesl Schillinger wrote, “there is perhaps no cartoon as coolly unsentimental as the Mother’s Day cover Will Cotton drew for the May 11, 1935, issue.”

The fires that have ravaged the city of California amidst the changing environment, burning through some forty thousand acres so far. The wildfires are among the most dramatic examples of climate change. Artist Till Lauren portrays the burning fires on the cover to give a visual of the raging heat in the infamous California, the city of the stars.

Kerry James Marshall’s reinterpretation opens Eustace, the mascot of New Yorker’s eyes as he closely observes a butterfly drone. In this rendition we also get to see the butterfly’s point of view within the dandy robot’s chest. This particular and recent cover celebrating New Yorkers centenary timeline is a complex commentary that only a visual narrative could possibly achieve with such nuance. Marshall’s cover is a play on Irvin’s original wit into our century, prompting reflection on how technology and A.I. are reshaping our understanding of human nature.

Feature Image Courtesy- backdrophome