Artist and writer Art Castillo was a regular at Jimmy's in Hyde Park in the 1950s. Credit: courtesy John Ottenheimer

“Looking for someone?”

He blends in with the rest of the bar so much that I almost don’t notice him at first. My inquisitor looks like every man of a certain age at Jimmy’s: craggy, lichenous, and too observant for his own good. It’s a gray January day, just weeks before the 55th Street bar would retreat into COVID-forced hibernation, and I am doing just that—searching.

The object of my fixation is a panorama, roughly two-by-five-foot, depicting a lively night at Jimmy’s in the mid-1950s. You’d think you couldn’t miss it—the tableau is nailed to the wall facing the front door—and yet, I never noticed it in my years living in Hyde Park, nor have any of my friends. The black and white ink style and detail of its 100-plus subjects is remarkable, even Hirschfeldian. The patrons aren’t celebrities by any means, but they might have been minor ones to anyone living in Hyde Park at that time: You can spot Andrew Duncan (a founding member of Second City’s predecessor, the Compass Players) in a faux-military costume; Joffre Stewart (a poet, pacifist, and pamphleteer immortalized in Allen Ginsburg’s Howl) emptying a trash can on some men in suits; Ed Bland and Nelam Hill (directors-to-be of the seminal 1959 film The Cry of Jazz) debating at a front table; among countless others.

It’s an astonishing artifact, a historian’s dream. But age has done the yellowing, fading display no kindnesses. The boldest part of the frontispiece is a signature in the lower right corner: “Art Castillo.”

Moulin Jimmy’s is a snapshot of Hyde Park as it once was.Credit: hannah edgar

When he drew Moulin Jimmy’s, as the original artwork is fondly known to its few surviving subjects, Arturo (later Arthur) Teodoro Castillo was a 24-year-old contradiction—not a University of Chicago student, but part of the institution’s intellectual orbit; a keen observer of Hyde Park’s social intricacies, but not much of a talker himself; a caricaturist who regaled his friends with inked likenesses, but who considered himself primarily a writer.

At least, that’s how his best friend John Ottenheimer remembers him. A retired architect, Ottenheimer once apprenticed for Frank Lloyd Wright; he designed the lettering on the Guggenheim’s façade. Now 87, Ottenheimer lives alone on Whidbey Island, a sleepy isle in Puget Sound. He’s the keeper of Castillo’s archives—sketches, correspondence, novel and libretto drafts, photos, and mountains upon mountains of books.

“A lot of the story of Art is all of the people he knew, and he was interested in people,” Ottenheimer tells me during one of our half-dozen phone conversations. “That’s why his caricatures are all so accurate: He perceived not only their features in detail, but he also perceived their inner nature.”

Born to a white Kansan mother and Filipino immigrant father in 1930, Castillo grew up in nearby Washington Park, Woodlawn, and Bronzeville, among the most racially integrated neighborhoods in the city; the year Art was born, the Castillos were one of several Filipino and mixed-race families on their block on East 55th Place. He attended Oakenwald Elementary in Bronzeville (now demolished) before his parents relocated to Jefferson Park.

Castillo was never one to conform to expectations, parental, societal, or otherwise. He never graduated from Taft High School (likely too bored or too socially alienated to stick around) and went to dramatic lengths to dodge the draft, from fleeing the FBI to staging his own suicide. He eventually made his way back to the south side and fell in with a band of misfits living in Whitman House, an integrated, co-ed cooperative at 5721 S. Kenwood. Ottenheimer was among them—”and if you couldn’t find us at Whitman House, you could find us at Jimmy’s.”

Then and now, no Hyde Parker calls the bar “Woodlawn Tap,” though that might be the watering hole’s formal name. To patrons, it’s always been Jimmy’s, after the late James Wilson, its longtime owner and barkeep. He’s in Moulin Jimmy’s too, of course, cradling heaps of cash behind the bar. Over his shoulder is Art’s sendup of a backlit University of Chicago seal (here a cooked bird instead of a phoenix), which still looms over the center of the bar. Ottenheimer’s likeness shows off a pamphlet titled “Wright Is Love” in the bottom-right corner of the tableau. Nearby is George Tolley, an economics professor emeritus at U of C and acquaintance of Castillo’s. He still lives in Hyde Park, but spoke to me while hunkered down in Michigan.

“A lot of the story of Art is all of the people he knew, and he was interested in people. That’s why his caricatures are all so accurate: He perceived not only their features in detail, but he also perceived their inner nature.”Credit: hannah edgar

“It was a very lively place, with lots of talented and colorful people around, students and non-students alike,” Tolley recalls. “That was probably a pretty representative group in that tableau.”

Before completing the Jimmy’s panorama in 1955, Castillo captured a morsel of Hyde Park life in a similar drawing of Steinway’s Drugstore, a long-gone deli at 57th and Kenwood—this ink piece is now part of Ottenheimer’s private collection. Many of the same figures in the Steinway’s drawing—which Art signed “Salvador Dilly”—return in Moulin Jimmy’s. Though he sold prints of Moulin Jimmy’s for $1, neither were commissioned works; to Castillo, the panoramas were more or less anthropological studies. Another acquaintance recalls that Castillo obsessively drew “sociographs,” charts that mapped the social networks of other Hyde Parkers.

Castillo’s irrepressible impulse to taxonomize other people crops up again and again in his work. At the time of his death in 1962, he’d mapped out an ambitious, Ulysses-esque novel outlining different archetypes of human nature, lifting concepts from philosophy, psychology, art, literature, and more. He hoped it would be his magnum opus.

“[The Rite of Spring] is a sober and penetrating study of the Cultural Deviant, of those keenly sensitive and intelligent individuals confined to the periphery of society by the studied mediocrity of their fellow man,” Castillo wrote in an apparent foreword to the novel. “It is a study of their Society, of the little Parises, the Greenwich Villages, the Cape Cobs, the Fisherman’s Wharfs, the Lower Basin Streets, the Hyde Park bohemias into which the delta of the Great American Damned gravitate with inevitable and terrible cohesion.”

Cartooning may not have been Castillo’s be-all end-all, but it was certainly most revealing of how he viewed the world. Plus, it paid the bills, at least for a time. Throughout his career, Castillo’s biggest commissioner was Doubt, a magazine put out by the anti-government, anti-science Fortean Society, as well as a handful of sci-fi fanzines. The closest Castillo came to going corporate was painting window displays for department stores and illustration work for Mages Sporting Goods. Both gigs were, unsurprisingly, short-lived.

“While I knew him, I don’t recall Art holding a nine-to-five,” Ottenheimer says. It simply wasn’t his way.

If I were a more apologetic writer, I might call Castillo “complicated,” an adjective often flung over egoists like a tablecloth. Judging by his correspondence, Castillo could be self-absorbed, even callous. His parents adored him, but he rarely reciprocated their warmth, and even then, usually only when he needed cash. (Unfortunately, his spotty finances meant he could rarely support his own child, to the point that he was once arrested for missed child support payments.)

For as sensitively as he assessed the inner lives of others, Castillo could be hot and cold with his romantic partners, too. You see this in Moulin Jimmy’s: Often, Castillo knew which of his friends were about to leave one lover for another before their partners did, so he drew them positioned between their two love interests, turning their gaze from one to the other. He even depicted himself doing the same, sitting at a table with his dark-haired, kind-eyed wife but angling himself towards a long-lashed blonde.

But the panorama captures much more than petty interpersonal drama. It’s a snapshot of Hyde Park as it once was—dense, bustling, and earnestly, uniquely polyglot. It was also a Hyde Park that wouldn’t last. After the Supreme Court declared restrictive covenants unconstitutional in 1948, the University of Chicago flailed to halt the influx of lower-class Black Chicagoans into Hyde Park, first by a series of clearance projects under the aegis of the South East Chicago Commission, then with a federally backed urban renewal plan that won the backing of City Council in 1958. Whole blocks were razed and suburbanized; the streets became a maze of one-ways and dead ends.

Then, the collateral. Pre-urban renewal, dozens of taverns, clubs, and small businesses lined Hyde Park’s arterial streets. By the end of the 1960s, only a select few survived. Gone was Compass Theater, the birthplace of improv comedy, once just a few doors down from Jimmy’s. Gone, too, was the Beehive, the smoky jazz club where Charlie Parker performed one of his last gigs, seared off the map by a behemoth I.M. Pei housing complex that still bisects 55th Street. All in all, an estimated 4,000 families were displaced, most of whom were Black.

Planners maintained, truthfully, the resultant Hyde Park would be integrated, too—just on the university’s terms. But to many cosmopolitan Hyde Parkers, urban renewal changed the neighborhood for the worse. A cynical motto trumpeted Hyde Park as the place where “Black and white united against the poor.”

“Frankly, the neighborhood today is a shadow of its former self,” Tolley tells me. “It was a more heterogeneous place before, more avant garde. It might have even been ahead of Berkeley.”

Many disenchanted Whitmanites fled for the coasts—some to New York, and others, in fact, to Berkeley. Castillo did both, spending stints in Greenwich Village, the Bay Area, and Mexico between the completion of Moulin Jimmy’s and his death from colon cancer seven years later. His mother Dorothy had moved to Kansas some years after becoming widowed; by then divorced and alone, Art followed her there to live out his final days.

Art Castillo at the Message Tree, which used to stand at West 57th Street and South Kimbark Avenue.Credit: courtesy John Ottenheimer

Despite his bleak prognosis, Castillo’s final letters, like so much of his correspondence, fixate on the future—on new projects, the particulars of his legacy, conversations with friends. In his final letter to Ottenheimer, dated March 1962, he inquires after the state of some treasured items and urges his friend to keep writing him. “When you return in May, you may expect to find me as you left me, still bed-ridden,” Castillo laments. “I am beginning to look dismally ahead to a long career as an invalid.”

Of course, there would be no next time, and no long career. Castillo died on April 19, 1962. He was 32 years old.

Moulin Jimmy’s started out a utopia and ended up a graveyard. Did Castillo know it, then, that in just a few short years, the neighborhood—and by extension, Jimmy’s—would never look the same? That his Hyde Park was little more than a glimmer, soon to succumb to the twin entropies of racism and classism? Looking at the artist’s own worn, sharp-cheekboned visage surveying the scene like a hawk from the bottom-right corner, I feel as though he must have.

The Ahab at the bar was right. I started this whole thing looking for someone, and ended it looking for somewhere—somewhere that doesn’t exist, strictly speaking. Funny thing about Hyde Parkers, though: We might sound disillusioned, but in reality, we’re starry-eyed optimists, the whole lot. Have to be.

Finally, I answer him: “Yeah. I am.” And resolve to keep looking.   v