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One More Day in the Life of Jason Pickleman

Artists flock to the flamboyant Book of Revelation: it is theatrical and evocative, thronged with doomsday terrors and prophetic visions. William Blake mined it for inspiration as did Jim Morrison. But in the final years of his life, as he attempted to make sense of his spectacular downfall, Oscar Wilde turned to the Book of Job, a story difficult to narrate as a morality tale. In it, Satan smugly wagers God that, when a mortal man experiences enough suffering, his faith will be swept away. One after another, Job’s comforts disappear. He is stripped of his possessions, his family killed, his livelihood reduced to ashes. Job’s body erupts with painful boils. His friends abandon him.

The plotline is low-key and the trials that Job undergoes don’t descend into melodrama; his is a quiet, quotidian tragedy. In the end, there is no satisfying answer to the question of an unjust universe raised by Job’s misfortunes. Suffering falls like the guillotine. And when the blade lifts again, can justice be said to be restored? I was introduced to the Book of Job in college by a young Jesuit brother. It occurs to me again, as I walk up the Chicago Lakefront with Jason Pickleman, who is gazing intensely at the gravel path directly in front of his shoes.

Pickleman is a myth in miniature. He is slight and moves with a hint of impatience. For decades, his uniform has featured cardigans and white button-downs cut by the likes of Comme des Garçons, draped over cropped trousers. As he does on our walk, Pickleman usually carries a cloth tote bag over his shoulder. His head and face are shaved clean. He wears a grin that is disarming but not entirely innocent. In the sunlight, he squints.

Pickleman’s myth, like any such myth, doesn’t precisely conform to the shape of his life. Because he is a dazzlingly prolific graphic designer, and an avid collector of contemporary art, and a devoted musician and poet, and a fixture of the social scene, and many other things besides, he finds himself engulfed in an artifice only partly of his own making. His myth burdens him this afternoon, as does his mortality. It isn’t just that he is dying, but that there is so much left to do.

JNL Graphic Design studio/courtesy JNL Graphic Design

In the days ahead he would be packing up his studio, with crates of pictures and sculptures and books and his beloved objets trouvé dispersed or confined to indefinite storage. He is under pressure to sort through his vast personal archive in preparation for handing it over to Columbia College. Curators from Wright have foraged through the studio, selecting amid the chaos the choicest lots for an upcoming auction. Still there is too much stuff, too much myth, too much everything. Plus, these days, even though he’d ended chemo and radiation treatments, Pickleman tires easily.

His body feels sore. The diagnosis came last spring when Pickleman checked into an emergency room after losing consciousness. He picked up when I called last March. “I have a hole in my head,” he said. Pickleman’s wife, Leslie Bodenstein, took the phone. They were driving home from the hospital, she clarified. Pickleman was diagnosed with high-grade glioma, an aggressive brain cancer. There was no cure.

The year had already been turbulent. Pickleman’s pet project, the contemporary art space Lawrence & Clark, had concluded its run. JNL Graphic Design, the practice that had been his creative home, was closing and vacating the space which it occupied for more than two decades. His father’s health was in decline. His personal life too seemed precarious in the months leading to the emergency hospitalization. But on the other end of the line, Pickleman sounded upbeat.

Pickleman was a skateboarder before he was a tastemaker. At Boston University, where he and Bodenstein met, he skated to zine shops on Newbury Street and to demimonde clubs for punk-rock shows. After graduating in 1987, he packed up his car and headed home to Chicago. Without formal training in design, he apprenticed at a local graphics studio and by 1992 established, with Bodenstein, JNL. From the beginning, he felt ambivalent about identifying with the design field. “I realized,” he tells me, “that you have to stop looking at their magazines and belonging to their societies. I started going to the Art Institute to grow as a designer.”

At the Art Institute of Chicago, Pickleman fully metabolized the collection. His recall of it is legendary, and he performs it as an exquisite parlor trick. He says, “describe any painting in any museum and I can probably name it.” Over the years, JNL designed plenty of work for the Art Institute. Other arts and cultural institutions crowded the studio’s portfolio: Museum of Contemporary Photography, Renaissance Society, Millennium Park Foundation, Chicago Architecture Center, Elmhurst Art Museum, Hyde Park Art Center, Driehaus Museum, the Poetry Foundation, Rhona Hoffman Gallery, Chicago Loop Alliance, Expo Chicago, Wright Auction. Pickleman met the then-aspiring midcentury modernism expert Richard Wright in Boston in the mid-1980s. When Wright’s auction house launched, Pickleman created its first advertisement. “It was maybe too tongue-in-cheek,” Pickleman says. “I don’t know that Richard ever ran it. I don’t even know that a copy exists.” The design, as he remembers it, mimicked print ads for discount furniture stores, with “lots of big callouts and starbursts. ‘NEED FURNITURE?’ So I used that vocabulary.”

Pickleman is in the dining room of the Lakeview home he shares with Bodenstein, seated against a backdrop of walls and sideboards overflowing with art. The crisp sunlight coming through a picture window casts a grid of shadows, dividing surfaces into panels like a comic strip. Pickleman dares me to test his memory. On a visit to the John Michael Kohler Arts Center, I lingered at a tableau, a grid of drawings, industrial detritus, and ritual objects that brought to mind the assemblages on Pickleman’s walls. “Ray Yoshida,” Pickleman says definitively. “It’s one of my superpowers, despite my failing faculties. The brain cancer is disrupting my executive function.” He holds eye contact for a beat. “Who even knew I had one of those?”

It is time for Pickleman’s daily walk along the Lakefront, a ritual that predates his illness. Bodenstein makes us promise to keep our phones on, to bring sunglasses, and to use the building’s elevator. “Don’t let him pick up any trash,” Bodenstein instructs as we leave. Pickleman heads directly down a flight of stairs. No sooner have we crossed Lake Shore Drive than he spots his first piece of trash. Friends of Pickleman’s refer to this peculiarity as his community service. He strides ahead of me, keeping focused on the ground as he scans tree beds and concrete embankments for cigarette butts.

Our route leads past a thirty-foot-tall steel sculpture, a quintessential Keith Haring silhouette painted a vibrant green. The sculpture anchors the new AIDS Garden that commemorates the history of the Belmont Rocks, once Chicago’s main queer rendezvous. Since 2003, Pickleman advocated for its installation and participated in its commissioning. When the AIDS Garden was finally completed in 2022, he wrote an overview that quotes Haring: “The world doesn’t want these things and doesn’t need these things, but when they are here, they are here.”

We sit on a bench at the end of a pier. A sailboat heads out of the safety of the harbor into the open water. His illness is a mixed bag, he says, its contents wonderfully varied with regret and self-knowledge. He misses writing poetry, but is watching more television and binging the reality series “Dr. Pimple Popper.” He finds his energy for social engagements waning, which forces him to be more particular in his choice of friends and well-wishers. Although he is grateful to his wife, mother and son for caring for him, he bristles at limitations on his autonomy. His relationship with his adult son seems somehow less familiar, while that with his brother has grown more intimate. A spiritual advisor provided by hospice brought a measure of insight, but did not change the fact that he is in hospice care. For years, he assumed the role of custodian over this Lakefront patch, advancing public art and collecting discarded cigarettes. Now who will pick up after these people? Who will pick up after him? Regarding his private life, Pickleman asks for my discretion. Just then, Bodenstein comes looking for us.

Pickleman was expected back for lunch, followed by more sorting and packing at the studio. Bodenstein conducts the affairs of the household and the design business with yogic calm and economy of movement. Her command of her kitchen is so exemplary that she was the subject of observation by researchers at the design and innovation firm IDEO. At JNL, Bodenstein’s desk was on the studio’s main level, positioned to face the entrance. It was an oasis of sanity in an environment otherwise determined to overstimulate the senses. Pickleman’s work area was in the loft above, where the air is thinner. It was crowded by sound equipment, stacks of art catalogs, and bottles of fine whiskey. JNL’s lease expired last November, but the design practice was officially closed on May 31.

JNL had been a tenant in the former post office on Chicago Avenue since 1999. Back then, Pickleman was looking for studio space when he bumped into a friend, a real estate developer, on the sidewalk. The developer had just closed on a vacant building and Pickleman accompanied him inside. On the second story, where generations of workers had sorted mail under skylights, they discovered the remnants of a commercial photography studio. Inside was an old infinity wall, the curves of the cyclorama resembling a skateboard ramp. JNL moved in.

Back at home, Pickleman picks up a photograph from the kitchen counter. It captured him and Bodenstein at some party, smiling toward one another. How young and indomitable they seemed, I thought, how utterly free. Pickleman considers. “I can still fit into those Jean Paul Gaultier pants,” he says.

Going to and coming from parties, hosting them, surreptitiously entering them, getting booted out of them, whirling in them has long been its own performance practice for Pickleman. Seemingly no cocktail hour, fundraising luncheon, gallery opening, soirée of any stripe, charity event, bar mitzvah or baby shower, society vacation, or gala dinner would ever be complete without his appearance. Arts institutions among the JNL client roster help fill the social calendar. But Pickleman’s epicureanism—as his creative influence—extends into other spheres. For One Off Hospitality Group, the restaurant empire of Donnie Madia, Pickleman’s fingerprints are on virtually every marquee and menu. When Madia puzzled over the concept for what would become the mainstay West Loop eatery avec more than twenty years ago, Pickleman zeroed in on its essence as surely as scraping marrow out of a bone. The restaurant’s dishes emphasized pairings; its narrow interior and closely spaced seating promoted chance meetings. The throughline, Pickleman offered, was “with”: this with that, we with them. The name “avec” stuck. When the Publican followed with a meat-forward menu, Pickleman didn’t stop at designing signs and packaging. One Off published a limited run of Pickleman’s book of verse, part culinary koans, part barroom toasts, part marketing collateral:

Gorging, Feasting, Toasting, Fetê-ing —
glasses raised, good cheer begetting
the Gastronome,
and the Cook Aesthete.

Some graphic designers are hired to bang out a job and hurry on. Pickleman’s relationship with his clients is the exact opposite: he comes to eat and stays to design. And then returns to fetê thereafter.

We share a carryout meal from Ann Sather that arrives in bags designed by Pickleman’s Lakeview neighbor, the graphic artist David Lee Csicsko—pancakes heaped with cream, eggs and ribbons of smoked salmon. Whatever effects the illness has wrought, it did not diminish Pickleman’s appetite. Soon after his diagnosis became public, the doorstep of Pickleman and Bodenstein’s building was inundated with gifts, many of them bottles of spirits and fancifully packaged pot. Bodenstein was forced to send polite reminders that drinking and smoking were counterproductive. Lately people have been bringing over food.

Like Madia, Joe Shanahan’s entertainment business benefited from Pickleman’s presence. He, too, has remained loyal to Pickleman over the course of their decades-long friendship. Shanahan, the dean of independent music in Chicago, stands me a drink at his Gman Tavern, just north of the building that houses his venues Metro and Smartbar. His face, a study in composure occasionally accentuated with concert-grade earplugs, is partly bandaged. “Skin cancer,” he shrugs. It wasn’t his first round. Pickleman was a regular at Smartbar, a dancefloor dervish who came in after work and often stayed until the end of the night. “I learned a lot about dance from him. He knows a lot about ballet, he knows a lot about modern dance,” Shanahan later tells me. He misses seeing Pickleman burst through the doors of the club, as he had a thousand times before. Lately, he’s taken to texting messages and pictures that might lift his friend’s spirits.

The sign above the Smartbar entrance depicts a woman in a cocktail dress, appearing to look into her own reflection, getting ready for a night out. The image is an inky monochrome, an homage to a swinging era of postwar pinups. Yet it’s also punky in its photocopied, DIY-zine rawness. Shanahan asked for a new logo design for the club’s anniversary. The logo for Metro, the upstairs concert venue, was drawn by the legendary Factory Records graphic artist Peter Saville. Serious about its bona fides, the identity was—Shanahan hesitates— “Very… Metro.” For Smartbar, whose vaguely self-deprecating motto is high-IQ fun, the two decided on a lighter touch. “It was very pop art, very readymade. An identifier, like a sticker, that I was so drawn to.” Shanahan recalls how immersed Pickleman was in the physical production of the sign, for which he specified materials and dimensions: “It still hangs there, twenty-five years later.” The original artwork is now framed in Shanahan’s house. Pickleman gave it to him as a gift recently. “It shouldn’t be in my studio anymore,” he told Shanahan. During our lunch, Pickleman tells me that “clarity is king” in JNL’s work—the more obvious, the better. “My design instincts are pretty direct,” Pickleman says. “The DNA of a brand is on the first page. But sometimes it takes another ninety-nine pages to hone it.” As he wrote of Haring’s Lakefront sculpture, “obvious doesn’t come easily.” There is no one guiding visual philosophy, no single narrative that makes the corpus intelligible: “JNL doesn’t have an aesthetic,” he says. What binds the body of work together is a Picklemanian sensibility, idiosyncratic and erudite.

The storefront gallery Lawrence & Clark was the platform for his ever-deepening dive into the history of the art canon. Over a five-year tenure ending in late 2020, Lawrence & Clark showed dozens of rotating exhibitions that remixed Pickleman’s collection and presented new work. Its catalog was typical of Pickleman’s preoccupation with the spectrum of contemporary art and commercial kitsch, with cultural fluency and rule-flouting. The shows were mimetic, knowing: alongside “facsimile silver clouds” officially licensed by the Andy Warhol Foundation for the Visual Arts, Pickleman’s collection included Sunday B. Morning’s uncanny copies of Warhol’s Marilyn Monroe, and Pickleman’s own original “Another Pink Disaster,” a Warhol-inspired meditation on destruction. Similarly, for an exhibition entitled “SEX” that displayed work by significant contemporary artists, Pickleman recreated a giant latex-wrapped pink sign (spelling out the title of the exhibition, naturally) that had graced the London storefront of Vivienne Westwood and Malcolm McLaren’s boutique SEX in the mid-1970s. I wondered if Pickleman’s wardrobe referred to Miles Davis’ preference for neat khakis and Oxford shirts: by deadpanning country club prep, it makes the entire business seem perverse, a simulacrum of a simulacrum, a cosplay of cosplay.

The Wright auction of Pickleman’s collection is scheduled for the following day and so I rush over to the West Loop to catch the preview. I had come to know Pickleman as warm and generous, as someone who possesses a limitless patience for the things and people he loves. Over the years, I have witnessed him at work, accepting edits from clients, reworking designs, applying strip after humble strip of vinyl graphics at an exhibition. But I also know him to be a critical, at times truculent, jurist on matters of art and culture. The organizers of the Wright auction paid tribute to both extremes, the generous collector and the discerning critic. “Every Day is Different: the Collection of Jason Pickleman” sprawled across multiple rooms and two floors, with 220 lots of objects, many familiar to regulars of Lawrence & Clark. Pink SEX hung in the air, above a staircase. Mingled with Pickleman’s oils and collages were pieces by Judy Ledgerwood, Kara Walker, Wesley Willis and Jenny Holzer. Toward the entrance, a pair of toilet seats by the avant-garde artist Puppies Puppies was mounted on a wall. They were estimated to fetch between $3,000 and $5,000. A two-foot-tall acrylic ampersand, of no particular pedigree, sat against a nearby wall. Pickleman had discovered it just the other day, he says, while rummaging through JNL’s storage. “I’m most interested in ambiguity and pieces that seem strange or awkward,” he reported in the auction’s materials.

Peter Jefferson, amiable and loose-limbed, greets me in the front gallery. As Wright’s auction specialist, he had free rein of the JNL studio during the previous months to cull pieces for “Every Day is Different.” In concert with Pickleman and Bodenstein, he weighed and valued thousands of pieces. He quickly gave up any hope of curatorial coherence. “It’s not like a ‘Postwar Design’ exhibition,” Jefferson scoffs. “There is no theme, other than Jason.”

Everything you need to know about graphic design, Pickleman tells me, is on the back of a T-shirt for a corporate run. It’s an abbreviated lesson in identity, in hierarchy, in American desires and fears. He muses that if he “were a professor at a design school, I’d make students study those T-shirts.” In collaboration with Tony Tasset, Pickleman made a limited series of NASCAR-style pit jackets, printed with a patchwork of corporate logos, from blue-chip investment firms to computer manufacturers to toy stores. Blockbuster’s blue rectangle dominates the front; Enron spreads across the shoulders. Their one common trait is obsolescence. From the center of American culture, these brands slipped toward the edges—whether by way of financial ruin or moral malaise—until they disappeared completely. Cultural traditions both high and low, the philosopher Walter Benjamin argued, result in their inevitable liquidation. I thought this sentiment worth printing on its own t-shirt. The auction listing estimated the artist’s proof of “Pit Jacket” to bring in a minimum of $1,500.

“If you look at it alone,” Jefferson says, “it’s like, whatever.” But when the auction resolves into view, it coalesces into a fullness, a lifetime. “It’s not easy to replicate someone’s eye,” he continues, “but it finds its path back to a kind of balance.” Jefferson escorts me upstairs, where I find Rick Valicenti, the preeminent designers’ designer, scanning the auction catalog. He has his eye on a few things, but does not say which. Next morning Valicenti would be outmaneuvering his colleagues and rivals, bidding for gerrymandered precincts of Pickleman’s assemblage. And then, in another day or two, according to Benjamin’s unrelenting law of liquidation, another auction would inevitably take over the walls. It is thanks to Pickleman that Valicenti and I are fellow alumni of a strange creative confraternity in remote New Mexico. As bidding on “Every Day is Different” gets underway, I board a flight to Albuquerque.

For more than ten years, JNL’s annual cycle was crowned by Expo Chicago. Expo required of Pickleman and Bodenstein a superhuman effort in order to stage one of the buzziest and best-attended international contemporary art fairs. Pickleman’s identity, the bold lettering of EXPO stacked atop CHGO, permeated Navy Pier and seeped far beyond. For weeks leading up to the opening of Expo, Pickleman spent every waking moment at Navy Pier. “He was everywhere. Once on site, he would be kind of a blur out there,” Tony Karman, Expo Chicago’s founder and director told me. “Obviously, he made his own beautiful work. But those weeks were his symphony and he was the maestro.” JNL produced catalogs and brochures; press kits, posters and step-and-repeats; badges, booth signs, ads, sponsor walls. When the fair was conceived, Karman said, he knew at once that Pickleman would shape it: “Jason was instrumental in every aspect of producing every piece of graphics on Navy Pier. What was wonderful is that I didn’t have to think about it at all.”

Pickleman has a particular fondness for arrows—the most direct of directions. At Navy Pier, wayfinding arrows navigated visitors through the maze of exhibitors, down corridors, up stairways. Even as Expo Chicago opened, he added and adjusted them to tune up the movement of the crowds. It was an instinct borne of his own vector-like path around the site, velocity inflected with direction. 2023 marked the first year Expo Chicago had to find its way without Pickleman, Karman told me. As a subtle tribute, Karman had installers attach graphic arrows to surfaces throughout Navy Pier. “When he came out to the opening, with Leslie, he noticed them all,” he said. “I put one arrow at the very end of the fair, high on a column, pointing toward the sky.” It is still there, on column number sixteen, and if Karman has his way, there it will remain.

As soon as the fair closed each year, Pickleman would travel to northern New Mexico, across terrain made famous by Georgia O’Keeffe’s paintings. He started visiting in the late nineties, soon after his Chicago Avenue landlord and longtime music-making partner had acquired, at the edge of the San Luis Valley, an expanse of basalt peaks, alpine meadows, lava fields and pastures eroded from a century of overgrazing. Log cabins clustered within earshot of a mountain stream. The air was scented with piñon smoke. The compound had rustic accommodations and a swimming pool shaded by a cliff, rising 2,500 feet above it. Pickleman began to observe an annual pilgrimage.

In 2012, Pickleman convinced the owner to organize a retreat and enlisted help from MAS Context founder Iker Gil. Chicago’s creative intelligentsia ascended the mountain and snugged up in log cabins. Days were a succession of hikes, communal meals and late-night conversations colored in with the giddiness and vulnerability of an overnight camp. There were few rules aside from Pickleman’s insistence that neither Post-it notes nor whiteboards would be tolerated, and that nothing was mandatory. He spent much of each day in his cabin, playing music, writing, avoiding people, listening to the sound of water splashing against boulders, and altering his consciousness. As he planned for the second iteration of the retreat, Pickleman suggested I might feel at ease there, too. That year, bleary after a three-hour commute by car from the Albuquerque International Sunport, I steered into a clearing at the foot of a cliff. Pickleman rose from the pool, gloriously nude, and improvised a short dance routine. Over the following years, the retreat hosted some 150 painters, poets, photographers, ecologists, techies, foodies and people who, like Pickleman, elude disciplinary categorization.

In 2022, shortly before receiving his cancer diagnosis, Pickleman returned to New Mexico to take part in a ten-year alumni reunion. Expo was mercifully over and Lawrence & Clark had shuttered. Pickleman announced that he and Bodenstein decided not to renew JNL’s lease. He still swam in the buff, but those who knew him well noted a change. Standing in a meadow, Pickleman spoke with unusual emotion. He said he felt a shift coming. He felt it was time for whatever is next and he was ready for it. That next thing, he said, was freedom. Glioma affects the frontal lobe of the brain and is known to cause emotional changes. The disease erodes memory. Yet in that moment, Pickleman was not exercising his prodigious recall. He was looking at the landscape unfolding in front of him.

From his prison cell, Oscar Wilde wrote “De Profundis,” a long letter about his love for art that was published after his death. Wilde had lived a life of an extravagant dandy and a chronicler of his time. But the trials he endured left him with little desire to return to the society that had by turns extolled and vilified him. Its tastes now appeared capricious, its judgment unjust. Predictably, imprisonment soured Wilde; the letter inveighs against his captors and mourns the aesthetic scene he once so fully inhabited. In the end, though, “De Profundis” grasps toward release. If freedom were to be restored, Wilde swore that the “only people I would care to be with now are artists and people who have suffered: those who know what beauty is, and those who know what sorrow is.”

My plane from Chicago touches down. A couple next to me is planning an itinerary to O’Keeffe country, in the mountains above Santa Fe. I check my phone. In a text thread, Bodenstein sent a list of references to articles that Pickleman had published. Next, I scroll up through Pickleman’s messages from months and years before. “Don’t know when, or even if, I’m going to Expo,” one read. “Life took a weird turn.”