The first time I met Molly Crabapple, she was sitting on the floor of her Manhattan loft, surrounded by art—a vision of bohemian glamor as she smoked cigarette after cigarette, eyes rimmed in winged black liner. She talked fast and worked faster, moving with speed and acuity through various topics as she prepared the gluey pot of wheatpaste we would later use to erect posters of her art all around the city. I had just finished an article on autonomous zones, and we quickly bonded over their strange, transient beauty—something she had witnessed firsthand while participating in the Occupy Wall Street movement, and during her time reporting on the Greek anarchist refuge Exarchia.

An award-winning artist, journalist, author, and activist, Crabapple has traveled the world to document moments of political unrest—placing herself on the front lines of global conflict, armed with only a pen and paper. She has reported on the Russian invasion of Ukraine, Lebanese snipers, Pennsylvania prisons, and the ravages of Hurricane Maria in her native Puerto Rico, capturing the human impact of social and economic injustice. Magazines describe her as a “punk Joan Didion,” “a young Patti Smith with paint on her hands,” “a twenty-first century Sylvia Plath,” “art’s Alexandria Ocasio-Cortez,” and “the Millennial generation’s first great radical artist.” She is, as Deb Olin Unwerth wrote for the New York Times, “a lion for her own cause—ferocious and feminist, hardworking and weepy—a new model for this century’s young woman.”

She’s also my friend, which is why I found myself near-naked in her apartment on a chilly February day, posing for a portrait. It seemed a fitting bookend to our first encounter: Crabapple’s hands moving quickly as we talked, making tiny adjustments with the quiet confidence of someone whose craft has become second nature. She would look up at me, down at her canvas, up at me again; then, only two hours later, she handed me a painting—one of several featured in The Chair Series, her new exhibition at New York’s Postmasters Gallery. In it, Crabapple documents friends and acquaintances from all walks of life: fire eaters and sex workers, philosophers and poets, united by the shared act of posing in the antique swoop-backed armchair she inherited from her great-grandmother, Rose. The series, which Crabapple describes as her most personal yet, originated from feelings of disillusionment born of bearing witness to the world’s suffering—first, as she documented war-torn Syria for her book Brothers of a Gun, and later in pandemic-era New York. “After witnessing so much misery and death, I wanted to do something that was about life,” she says. “No photos, no tech, no screens. Old-school. Just some music on vinyl, me, the pigment, my subject, and a chair.”

At the show’s opening, the titular chair could be seen at the center of the gallery: as baroque and beautiful as a Crabapple painting, with its sunset-colored velvet upholstery and carved mahogany legs. Some people sat in it for a picture, but for the most part, the exhibition’s 400-some attendees filtered in around it, filling the large industrial space with pleasant chatter. They are friends and loved ones, collectors and diehard fans—some of whom flew from out of state to attend the opening, having fallen in love with Crabapple’s work. The people featured in the series take Polaroids with their portraits, rendered in bold strokes of acrylic, gouache, markers, ink, pastel—languid bodies and iron eyes, all of us fiercer and more beautiful than we are in life.

“I realized that art and action could infuse each other. A painting didn’t have to hang in a gallery dead as a pinned butterfly. Art could be gorgeous, engaged, and political, working defiant magic on the world.”

The daughter of an illustrator and a Marxist professor, Crabapple grew up surrounded by art and politics. Her mother worked late into the night designing children’s books and toy packaging, demonstrating that art was not just a rarified creative pursuit, but a means of economic survival; her father spun her bedtime stories about anti-colonialist pirates liberating slaves from sugar plantations, and told her that he had only two rules: “Question authority and be interesting.”

At age 12, Crabapple was diagnosed with oppositional defiant disorder, having spent her grade school years blaring punk rock on her Walkman, reading Marquis de Sade in class, and talking back to authority figures. At 17, she traveled the world, wandering the streets of Fez with her sketch pad and sleeping in bookshops in Paris. It was around this time that she took on the name Molly Crabapple, bestowed on her by an ex-boyfriend who suggested it described her personality: rebellious and defiant. A few years later, she had dropped out of art school, and was working as a nude model and burlesque dancer to make ends meet. “In the early days of my career, I was doing odd jobs on Craigslist to finance my art—dancing, posing for guys with cameras, just desperately trying to do every possible thing I could to get a fucking foothold in New York,” she says. “Because even then, I knew I would rather die than have a fucking normal life.”

Now 40, Crabapple’s life is as creative—and busy—as ever. The day we met for our interview, she had already given a speech at the New York Public Library, where she is a Cullman Fellow—clocking in every day to work on her forthcoming book about the Jewish Labour Bund, which involves learning Yiddish to trace her family’s activist history. The day before that, she was protesting at the Statue of Liberty, taking over the monument with other Jewish activists to urge for a ceasefire in Palestine. She’s tired, she says, but she still pulls out her chessboard to play while we talk; Fred Harper, her longtime partner, works on his own artwork in the background, sometimes chiming in to advise me on my moves.

It’s the first time we’ve hung out since I read her critically-acclaimed memoir, Drawing Blood, which charts Crabapple’s unconventional path to success—from her stint as a Suicide Girl to her years as a sideshow performer, walking on glass and swallowing fire to finance her art. After years of struggle, her first big break came when she became the first resident artist at the Box, an opulent club at the center of New York nightlife. A fly on the wall in the playground of the wealthy elite, Crabapple was fascinated by the class dynamics at play—witnessing, firsthand, the impact of the 2008 financial crisis and the economic divide between burlesque performers and the wealthy bankers they entertained. Growing increasingly disillusioned by the “drug-fueled circus of mutual exploitation,” Crabapple took her work in a new direction with Week in Hell: a crowdfunded performance piece in which she locked herself in a hotel room, covering its walls in paper and filling all 270 square feet with art while viewers watched on livestream. Eager to purge herself of the artistic clichés that no longer served her, Crabapple pushed herself to the limits, drawing until she could draw no more. She emerged exhausted, renewed, and ready for the next phase of her life. One week later, Occupy Wall Street started.

Crabapple threw herself into the movement, attending demonstrations and sketching the people on the front lines. When she wasn’t protesting at Zuccotti Square, she was hosting activists in her New York apartment, which soon became a sanctuary for reporters on deadline, typing alongside her as she made protest posters. Crabapple had grown up going to protests, but it wasn’t until Occupy that she realized the power of collective action—and of bearing witness to it through art. As she wrote in Drawing Blood, “I realized that art and action could infuse each other. A painting didn’t have to hang in a gallery dead as a pinned butterfly. It could exist in places where people cared as a mural, a stage set, a protest placard. Art could be gorgeous, engaged, and political, working defiant magic on the world.”

As a vocal advocate for labor rights, sex work, and humanitarian issues, Crabapple’s work has taken her from the courtrooms of Guantanamo Bay to riot-torn Greece to press conferences in Dubai, where she bypassed security to confront Donald Trump about the fact that the workers on his property there were paid only $100 a month. She has been arrested three times—twice for political causes, and once for doing graffiti—and spent her first stint in jail scratching drawings into a plastic cup. After her release, she was shocked to find that #FreeMollyCrabapple was trending on Twitter, having caught fire after she live-tweeted her arrest in handcuffs.

“Drawing was a way to bridge the gap between myself and other people. It was a way I could make friends. It was a way to approach strangers. It was my excuse to get into nightclubs, and prisons, and warzones. Drawing was my lockpick—and it allowed me to enter a whole new world.”

One year later, Crabapple returned to Zuccotti not physically, but metaphorically: releasing Shell Game, a series of nine allegorical paintings about the revolution and crisis of 2011. Crawling with detail and Crabapple’s signature blend of surrealism and satire, the paintings depict events including Occupy Wall Street, the American debt crisis, the corruption of the healthcare system, the work of hacker group Anonymous, and protests in Greece, Britain, Spain, and Tunisia. “In 2011, people around the world broke consensus with power. They sat down in the main squares of their cities—Tahrir, Syntagma, Puerta del Sol, Zuccotti—and declared that the old machines were defunct,” she told WIRED. “It was a ferociously urgent year. Things, for the first time in a long time, felt like they might change—that a new world itself might be at the end of a street demonstration.”

Though many of these movements have been crushed or mutated, corrupted or stalled, Crabapple hasn’t stopped fighting. She has pioneered a new genre of live-illustrated journalism, collaborating with Alexandria Ocasio-Cortez, Jay-Z, Amnesty International, Human Rights Watch, and the ACLU on Emmy-nominated animations. Her books Discordia and Brothers of a Gun—produced in collaboration with Laurie Penny and Marwan Hisham respectively—battle injustice with word and image, bearing witness to the human cost of global conflict. A vocal advocate for workers’ rights, she has publicly lobbied against the impact of AI, documented the victories of New York cabbies, and held shady landlords to account.

Though Crabapple’s work can now be found in the permanent collections of the United States Library of Congress, Columbia University, the Museum of Modern Art, and the New-York Historical Society, you’re just as likely to see it on protest signs—or spot her in the streets, jumping police barricades in heels, as one fan observed. Perhaps you’ll run into her at the New York Public Library, or at her favorite neighborhood haunt, Toñitas, a Puerto Rican social club with $3 beers and homemade food prepared each day by its beloved, eponymous matriarch. When she takes me there one warm summer day, she is greeted like a local celebrity, having befriended the regulars by drawing their portraits for free. It’s a habit she picked up in childhood—seeing her craft not as a rarified creative pursuit, but as a way of interacting with the world. “I like sketching strangers, because when you draw someone, they’re being seen in a new way, and you’re giving them the kind of close attention so many people never receive,” she says. “Growing up as a shy outcast, drawing was a way to bridge the gap between myself and other people. It was a way I could make friends. It was a way to approach strangers. It was my excuse to get into nightclubs, and prisons, and warzones. Drawing was my lockpick—and it allowed me to enter a whole new world.”

Crabapple’s latest exhibition, The Chair Series, is on view at New York’s Postmasters Gallery. There will be a live drawing session on December 9, and a closing party on December 15.