Click on the Flip-Flop icon on the iPhone or iPad app, POTUS Pick, a digital platform created by Pulitzer Prize-winning editorial cartoonist Ann Telnaes, and an image of President Barack Obama appears. It is an adroit caricature, emphasizing his brooding eyebrows and pokey ears. “We can’t just drill our way out of the problem,” we hear the president say. Suddenly Obama springs into a gymnastic flip, and intones, “I believe that we should continue to expand oil production in America.” Telnaes has scored her point: Obama is a flip-flopping president on the hotly contested issue of exploiting domestic oil deposits.

Welcome to the brave new world of political cartooning. With the decline of print media, where the art form has flourished for two and a half centuries, the future of political cartooning has been thrown into doubt. There are fewer than twenty-five full time staff editorial cartoonists working in the U.S. today, down from some three hundred as recently as 1990. But true to their combative spirit, American cartoonists are hardly going down without a fight. Growing numbers of them are finding creative ways to survive and flourish in the era of digital media, using innovative apps to display their wit, posting cartoons on new websites, and in some cases becoming gainfully employed by online publications. It may turn out that rather than killing the political cartoon by hastening the demise of the printed page, the Internet may revitalize the art form with an infusion of young, independent and more diverse voices.

Illustrated commentary is an American tradition dating back to at least 1754, when Benjamin Franklin published a wood-cut cartoon titled Join or Die in the Pennsylvania Gazette. Depicting a snake severed into eight parts representing different American colonies, it implored colonialists to unite in preparation for what the Americans called the French and Indian War. The editorial cartoonist holds an esteemed mantle in America; more vaunted than a mere satirist or illustrator. He or she is an ombudsman, holding public servants accountable for policies and gaffes. An exemplar of the craft was Thomas Nast, who launched his arrows from the pages of Harper’s Weekly in the late nineteenth century. Nast cartoons like one titled Who Stole the People’s Money famously helped bring down William M. “Boss” Tweed of the corrupt Tammany Hall political machine in New York. (Tweed purported demanded: “Stop them damned pictures. I don’t care so much what the papers say about me. My constituents can’t read. But, damn it, they can see pictures!”)

Generations of editorial cartoonists like Paul Conrad, recipient of three Pulitzer prizes while working for the Los Angeles Times, have followed in Nast’s footsteps. Conrad took on eleven American presidents, most notably excoriating President Richard Nixon for the criminal abuse of power known as the Watergate Scandal—an act that landed Conrad on Nixon’s infamous Enemies List. Long before the decline of print media, cartoonists battled for editorial space against editors fearful that their work would offend powerful interests or advertisers. “The way to succeed in this business is to play it safe, to crank out boring, derivative, redundant, often even plagiarized work,” explains syndicated cartoonist Ted Rall.

Gary Trudeau’s Doonesbury has gone a long way toward opening editorial cartoon space for dissent and controversy since he first published it in 1970. A fearless master of the art, his strip is syndicated to nearly 1,400 publications globally—and available online on the Slate website and at gocomics.com. His taboo-breaking mention of drugs (“fine, uncut Turkish hashish”) in a 1972 strip ignited protest from readers of family newspapers. He was the first syndicated cartoonist to draw an openly gay character. In 2003, Trudeau drove conservatives mad with an anti-war series that incorporated the names of U.S. soldiers killed in the American invasion of Iraq into his panels. From Richard Nixon onwards, he has consistently taken on American presidents; his strip once featured a contest asking readers to submit proof of George W. Bush’s military record, service that seemed to elude official documentation. Frequently, Trudeau has even annoyed the editors who contract his strip. Nearly thirty papers refused to publish a recent Doonesbury lampoon of Republican-backed legislation that Trudeau likened to a war on women’s reproductive rights.

Some of the hardest-hitting political analysis out there can now be found on left-leaning web sites like the Daily Kos, which features comics drawn by such artists as Jen Sorensen and Matt Bors. Sorensen’s SlowPoke comics, named for her measured drawing pace, are loaded with voluminous commentary,Simpsons-esque caricatures, and cynical wit. No fan of conservatives, nonetheless one of her cartoons featured a text-intensive chart showing how the policies of “Obama at his best” are remarkably similar to “Romney at his worst.” Bors is currently experimenting with online animations, a medium for which Mark Fiore was the first cartoonist to win a Pulitzer, in 2010. Bors’ Avenging Uterus superhero, mocking some Republican politicians’ obtuse statements about rape and abortion, is bound to offend.

Carving out a niche is not an easy thing for a cartoonist in an online environment saturated with wisecracks from anyone with a blog site or a Twitter account. But illustrators like Matt Wuerker are proving up to the challenge. He draws five cartoons a week for Politico, a high-end news organization that started up as an online outlet and now also publishes a print edition. Wuerker, who was encouraged as a child by his neighbor Paul Conrad, was awarded the 2012 Pulitzer Price for Editorial Cartooning for, “for his consistently fresh, funny cartoons, especially memorable for lampooning the partisan conflict that engulfed Washington,” according to the jury’s citation. “Cartoonists were creating memes before anyone had a clue what a meme was,” Wuerker wrote in the Columbia Journalism Review. “They were the original tweeters, long accustomed to boiling a thought down to 140 characters.”

Wuerker meanwhile has taken his cartoons digital with animations and even interactive games. His OBAMAgrams iPhone app enables the user to craft an animated telegram to the president in the Oval Office. Choose from a handful of actions for Obama to perform (answer the red telephone, hold a birthday cake, launch a missile, etc.), record your own dialogue, and then post it to YouTube or Facebook.

The new generation of editorial cartoonists is exploiting the advantages of speed and space afforded by the World Wide Web. Veteran illustrator Steve Brodner covered the 2012 Republican and Democratic conventions like a beat reporter for the Nation, posting 152 sketches in real time on the publication’s website. Quick pencil drawings of American ‘pols’ at work, which might have languished unseen in his sketchbook, appeared instantaneously on the Nation’s Live Art Blog. Brodner, who pioneered the animated cartoon for the New Yorker online, also regularly posted one-minute animations about the 2012 election on the website of the Washington Spectator. In one video, Brodner conducts the final interview with the Romney’s dog, famed for having traveled on the roof of the family’s car during a 1983 road trip. From the elderly care home, Seamus the dog laments, “I don’t know about forgiveness, but you got to salute [Romney] if just for his nerve,” then lifts one of his hind legs next to a television set flashing the candidate’s image. Likewise, Ann Telnaes, who publishes her cartoons on the Washington Post’s website, posts up-to-the-minute sketches on her personal blog. One doodle depicted President Obama as he prepared for his debates with challenger Mitt Romney. It showed Obama downing dozens of cups of coffee—the deep shading on the mugs and on Obama’s face capturing the incumbent’s angst. When Obama was re-elected a month later, she posted a simple sketch of the president’s ebullient smile, with its toothiness taking up the entire frame.

The web’s supremely visual and interactive nature is inspiring a genre in which cartoonists take on the role of reporter-storytellers. Susie Cagle, a staff writer at the Grist, an online environmental magazine, dodged police batons and teargas canisters covering the Occupy Oakland protests in 2011. She has also filed illustrated reports from places like medical marijuana centers that typically forbid cameras from capturing images. Her scoop on a chain of faith-based crisis pregnancy centers, which allegedly dispensed bogus medical advice to young women, led the San Francisco district attorney’s office to investigate. Another notable example of the genre is the Cartoon Movement, a collaborative web platform for cartoonists from around the world. It has published long-form comic reportage on irregular Mexican immigration into the U.S., the Army of God in the Congo, and the London Olympics. A group of cartoonists traveled together to Afghanistan in 2010 for a series of illustrated dispatches on America’s longest war. But it’s not so easy to travel abroad to a conflict zone on a cartoonist’s budget. Thus, Kickstarter, an online fundraising platform, was a major source of financing for their Afghan expedition. Similarly Bors is crowdfunding his ongoing work with the Cartoon Movement; in less than a month, he exceeded his $20,000 goal, the minimum required to publish Life Begins At Incorporation, a book of his cartoons and essays.

Even in the New York Times, once dubbed the Gray Lady for its text-heavy columns and dearth of images, we are seeing a nod to digitally inspired visual narrative in the form of a weekly comic strip, called The Strip, by Brian McFadden. That McFadden, whose weekly Big Fat Whale strip appears in alternative weeklies like the Boston Phoenix, now illustrates for the Sunday Review signals a new appetite for edge, rather than a safe roundup of syndicated cartoons.

Although McFadden has landed one of the most coveted jobs in the business, he remains a freelancer—the gig’s benefits don’t include a subscription to the Times, much less benefits like healthcare. Not to worry, the Boston-based cartoonist is covered by “public option” health insurance in Massachusetts, enacted when Mitt Romney was governor of the state—a fact that McFadden has used to mercilessly skewer Romney’s opposition to Obamacare. McFadden titled his talk at the recent American Association of Editorial Cartoonists’ annual confab in September “The Future of Freelance: Brought to you by RomneyCare.” “I have health insurance thanks to Mitt Romney,” McFadden deadpanned. Introducing his slideshow, he projected his Commonwealth Care card on the wall to drive the point home, before getting into a selection of his comics.

McFadden is taking on the media as well as politicians. In a multi-panel October strip, for example, he took a swipe at journalists for becoming too obsessed with the pyrotechnics of partisan rhetoric; The Strip led with a posted sign reading: “Lost: Issues,” which were “last seen before the G.O.P. primaries.” In the following panels, a voter, whistling while walking down the street, is not fazed by the incapacity of Obama and Romney to address vexing issues like income inequality, the Syrian war, indefinite detention (“Since it’s indefinite, I can worry about that later,” says the voter), and more. In the final panel, a TV broadcaster announces, “The candidate you don’t like committed a gaffe today.” The voter cheers. It is, indeed, one of the more astute insights into the sorry state of American politics in the presidential election year of 2012.

The Cairo Review is grateful to Matt Wuerker for his permission to publish his cartoons.

Jonathan Guyer is associate editor of the Cairo Review of Global Affairs and a Fulbright fellow researching political cartoons in Egypt. He previously served as a program associate for the New America Foundation’s Middle East Task Force in Washington, DC, and as assistant editor ofForeign Policy’s Middle East Channel. He has contributed to the National, Guardian, and Daily Beast. On Twitter: @mideastXmidwest.