Illustrations by Molly Crabapple courtesy of Molly Crabapple/HarperCollins

I first met Molly Crabapple while having my possessions processed at a holding center in Lower Manhattan. We had both been thrown in wagons and hauled into jail from protests marking the one-year anniversary of Occupy Wall Street, and after spending half the day into the early evening behind bars—her in a pen for women, me with the gentlemen sardine’d into a comparable halogenic nightmare—we briefly compared notes about our treatment at the hands of New York’s finest.

This is how the author draws blood in a mesmerizing, almost calming way: I thumbed through the recap of Crabapple’s arrest—and of events that have caused me physical pain and anxiety since—with a masochistic fascination that helped soothe the posttraumatic reeling I still endure all these years later. Like the moniker that she assumed to tackle insurmountable problems with key and brush strokes, Crabapple packs a bittersweet wit, an edge prone to illuminating gasoline rainbows in grey skies.

While it’s almost inconceivable now that she deservingly stands to win any number of literary awards, it wasn’t until following the aforementioned detention in September 2012 that Crabapple turned to prose—reporting for CNN, for the first time she documented her experience in writing as well as in illustrations. She grew up worshipping strong words; as a teenage loner, Crabapple often found salvation in the stacks of bookstores, and for a pair of stretches in her college years even bunked between antiquarian shelves among nomadic knowledge-seekers at the legendary Shakespeare and Company in Paris. By mining such trials and leveraging her knack for making the difficult task of spilling one’s guts look simpler than taking a leak, in Drawing Blood she proves once and for all that her reportorial chops are as sharp as her pen curls.  

Like those who offered jacket quotes—Rolling Stone polemicist and noted Crabapple enthusiast Matt Taibbi says she “could be this generation’s Charles Bukowski”—I see no lid on the potential reach or impact of her work. From the whimsical decay of splotchy sketches that warrant Magic Eye-level attention, to unpretentious travel flashbacks that address personal travails as well as the macro concerns of eroding urban authenticity and growing wealth disparity, her creations are sufficiently raw and radical to connect with sympathetic rebels, all while artistically accessible and beautiful enough to wind up on Pottery Barn bookshelves belonging to the very yuppie banker scoundrels Crabapple abhors.

Despite her working class roots and the hurdles she faced, Crabapple has been knocking on tall doors for some time. As she notes in Drawing Blood, she even managed to sell a small drawing to the New York Times 10 years ago at 22-years-old, while her relative artistic halcyon days—spent dutifully illustrating the pre-crash Manhattan party scene at the colorful nightclub the Box—had more rewards than not. Nevertheless, her ascent in the art world was also a hustle that multilaterally mimicked exploitative gigs she held down as a nude model and Suicide Girl, and herein we are granted access to the truly interesting underpinnings of an artist’s struggle that we rarely get to witness.

“America still believes that if you work hard enough, you’ll achieve your dreams,” Crabapple writes. “Go to college. Get a job. Put in the hours. The invisible hand will reward you with a home and enough money to take your kids to Disneyland. It’s a soothing lie. Any strawberry picker will tell you that hard work is a road to nowhere.”

At one point on her chosen road to somewhere—a pathway paved with grit but also on which capital and access are critical components of success—she describes “bonds formed running from cops” as “sweet with adrenaline and rage.” The same goes for Crabapple’s tales of penetrating a creative class that is as fickle as it’s superficial, and of her stories about learning about life with lovers and bohemians who she encountered from Far Rockaway to Northern Africa. As natural as her writing flows, there’s something of a metaphor in how she nursed an autobiography about hard work with such surgical rigor.

This message will hopefully be central to the book’s lasting impression—while Crabapple steers nowhere near the kind of woe-is-me theatrics common in political stump speeches, there’s nonetheless a theme of individual empowerment driving her life story. What separates the author from a shameless rags-to-riches evangelist like Ben Carson (besides her having integrity and lacking riches, of course) is that she acknowledges non-divine external factors. In explaining how she was only able to land that breakthrough $800 Times assignment after mailing $500 worth of postcards to art directors—that she printed and shipped using burlesque bucks—Crabapple writes, “Naked-girl money was my escape hatch. Without it, I’d never have been able to do the work that got me noticed.”

She continues: “Talent is essential, but cash buys the opportunity for that talent to be discovered. To pretend otherwise is to spit in the face of every broke genius. I am good, but it was never about just being good. It was about getting noticed.”

Here’s to noticing …

CF: It’s clear from your opening and from various comments throughout the book—“I was twenty-nine when I stood on that Guantanamo ferry. By that time, I had been drawing for twenty-five years.”—that you consider yourself an artist first and foremost, above all. But how much credit do you give your ability to write so passionately for your success in being able to disseminate your work so widely?

MC: A lot of artists who who are trained through master’s programs are trained to write in this arts jargon, which is presumably meaningful to people in that world but is alienating to everyone else. So I think that being able to write in a way that is clear to people who don’t consider themselves art scenesters is helpful. I started writing professionally just a little over three years ago. I did a few one-offs, but my first real thing was about my arrest.

I really wanted to be a writer when I was in high school, and I wrote this really terrible novel about time travel that no one is ever going to see … I slogged my way through this, but I was working really hard as an artist, so I just didn’t [write] because it was really hard for me. I was surrounded by all these brilliant writers, and I didn’t think I was capable of it, but through having this one piece and by having all these amazing writer friends mentor me I just made myself do it.

CF: You write that you “keep grudges for decades.” But there are moments in your book in which that doesn’t seem to really be the case. Is that how you describe yourself across the board? Or are there exceptions?

MC: I still hate my middle school principal who wanted me put on Lithium because I wasn’t obedient enough. I hate people like that. There are so few things that are liberating about writing a memoir, but one thing that is liberating is that you get to fact-check your past, and while you may have thought that you were done wrong, then you’re reading the old emails, and sometimes you were just being an asshole.

CF: You describe Shakespeare and Company in Paris as “a fortress, built from a past at once faded and imagined, when will and eccentricity were all one needed.” Are they no longer needed?

MC: I feel like because cities are so gentrified, and there is so much law and surveillance and rules, that there is very often less space for that—especially in cities like New York and Paris. But the idea that you would just have this amazing bookstore that sells really strange books, and that people who rolled up at it could just live there for free in exchange for pretty incompetent work, and that this wouldn’t fall apart but that it would keep going for 50-plus years, that’s an incredible thing. There are all sorts of co-ops and experiments, but in general they’re not that long lasting.

CF: The mayhem of a place like Fez, a visit to which you recount in the book—or even in a place like New York City—seems to drive a significant part of you. How much creativity could you muster in a lifeless, culture-less hellhole? What is it you love about chaos?

MC: Many people create great stuff in places that are quiet, but I can’t do it. [The city] is in my bones. That’s just where I am—I feel so miserable when I’m away from them. I kind of never leave my apartment anymore, but it destroys me how New York is being gutted. It’s eating itself. Not just shitting on working class people and broke artists, but now even successful businesses can’t survive in New York, because even a successful business can’t always pay $500,000 a month in rent. It’s destroying everything about this city. I know New Yorkers always say that, but I do believe we are at a particularly hideous moment for it.

CF: How much do you see your own life—free-spirited as it is—as being defined by all these moments you walk through—9-11, gentrification of the Lower East Side of Manhattan, the crash of the economy, Occupy Wall Street? For someone who is a bit of a loner, it seems like you sure like being in the middle of things.

MC: I think 9-11 fundamentally shaped those who went through it. That was ours, that was our tragedy, that was our neighbors getting murdered. And a lot of the country, in a lot of places where people have always hated New York, seemed to only really like us when 2,000 of us got burnt alive. 9-11 is something that I still get fucked up when I think about it. The reactions, what America did afterwards and the carnage that it unleashed, fundamentally shaped the world we live in.

CF: With all your history with Paris and with your beloved native New York—where in 2002 some restaurants on the Upper East Side had signs posted that read “We don’t serve French wine”—how do you feel about the events of the past month, and about the reinvigorated race to war?

MC: It’s fucking horrifying. What’s been happening in Syria has been a fucking nightmare for years, and it keeps getting worse. What makes me really angry about what happened in Paris is that these murderers who did this are EU citizens, who went to Syria probably to murder Syrian citizens, they use their first world passports to murder people in a third world country, then they take the fucking refugee route back, which was quite a deliberate thing, and then they do what they did holding fake Syrian passports, further terrorizing these people who they already terrorized.

CF: What kind of a reporter would you say you are? Participant? Fly on the wall?

MC: Just fumbling along [laughs]. I get called an activist sometimes in the press, and I don’t identify with that, because I’m not an organizer. I’ve never done that heavy organizational work, I just try and support with the best skills I have, which are usually artistic. When I think of activists, I think of Mariame Kaba of Prison Culture, or Robin Jacks [of Occupy Boston and No Boston 2024]—people like that, who are hardcore organizers. I wouldn’t necessarily say fly on the wall though, because when you’re drawing people, they notice you.

CF: There’s a scene in the book about your first attempt at a solo art show, in Williamsburg, which was a miserable failure. What kept you pushing through those times?

MC: I was a fucking Fashion Institute of Technology dropout—it’s not like there’s a lucrative corporate job waiting for me. What was I going to do? Either make it as an artist, or work retail. We don’t really live in a society that presents a lot of easy comfortable ways to make a living. It’s not like in Sweden, where you can get a dignified service job. I just can’t work in an office. There’s something screwy about my brain. I can’t do that sitting down and being obedient and looking professional thing. Eventually you get too old to do naked modeling, that’s not a long-term plan. I was going to do whatever it takes, because it was this or die in my mind.

CF: I was wondering how involved you are with sex worker activism these days. We have a new program in Boston that is essentially a just-say-no campaign for prostitution that is very top-down, essentially the sex trade equivalent of “Just Say No” to drugs. Generally speaking, how do you feel about these kinds of bureaucratic attempts to “rescue” sex workers?

MC: Fuck top-down. It’s always the same thing—people who are making their careers claiming they are speaking for people who they say are supposedly voiceless but who are actually shouting to be heard and are still being marginalized. I think this is an amazing time for sex worker activism. I’ve never been an organizer, but I try to do my part with drawing attention to stuff … The idea that [cops] are going to be saving women—it’s disgusting.

CF: At one point you describe an experience in 2006, in which you and another former Suicide Girl who is an artist were trying to get noticed at an underground art show, that caused you and to feel like you were “two sex worker shards washed up on the art world’s shores,” while “everyone legit was trying to kick [you] back out to sea.” But did you not see yourself as an artist first and foremost, even way back then?

MC: The art world to me was a network of like Chelsea galleries with big cube rooms and paintings that sold for $100,000 and curators who spoke in this strange special language. It was like the difference between being a writer and feeling at home in the New York publishing industry.

CF: In recalling your stint as the in-house artist at the Box, you write that “in New York, before the crash, this was all there was.” At the same time, you seem to be nostalgic for a time that wasn’t so great in the first place. Is that a fair characterization?

MC: You know how it is, when you sort of break through the first time … It’s like going into a nightclub for the first time, and you’re like, “Wow,” and there are all these lights, but then after you’ve been there for a little while, you start to realize that the music is kind of crap and the people are really mean. [The Box] was dazzling, and it had its own beauty to it as well as the horror, but if you don’t explain why these things were also dazzling, then it will never make sense why it ever appealed to anyone in the first place.

Molly Crabapple will read from Drawing Blood (HarperCollins) on Tuesday, Dec. 8 at 7pm at Brookline Booksmith, 279 Harvard St., Coolidge Corner. BrooklineBooksmith.com for more info.