Mr. Higgs first saw Mr. Koestenbaum’s paintings in early 2011 at the Atlanta Contemporary Art Center, where they shared space with works by Leigh Ledare, Tracey Emin and Laurel Nakadate, and immediately had the idea for a show.

Mr. Koestenbaum came to painting by way of writing. “I’ve always looked at painting and written about it and cared about it,” he told Gallerist. “I think when I wrote my biography of Andy Warhol, that was a real chance to apprentice myself to the way a painter proceeded.”

He said that he paints in “the mood of Joe Brainard or John Wesley, but with the procedure and crazy intensity of obsessive repeaters like Yayoi Kusama.”

He doesn’t have any plans to stop writing. He’s actually written two books since he started painting, and one of them, Humiliation—for which he wrote about things like the joys of amputee pornography and masturbating to the image of one of his 20-something students—earned him an art comparison. Literary critic Dwight Garner described the book in The New York Times as “The literary equivalent of Vito Acconci’s Seedbed”(1972), in which Mr. Acconci hid himself under a ramp at the Sonnabend Gallery and masturbated audibly.

“It’s quite risky.” said Mr. Higgs of Mr. Koestenbaum’s decision to show his paintings. “I think most people will come to the work with some pre-existing Wayne Koestenbaum baggage, and then they’ll have to work out what that means in relation to visual art by Wayne.”

“I am nervous about showing the work publicly,” Mr. Koestenbaum admitted. “I’m also entirely ecstatic. It seems like a fantasy of some wild Cinderella kind coming true.”

—Rozalia Jovanovic

Darren Bader's bulletin board. (Courtesy the artist and Venus Over Manhattan)

The second show at the new Upper East Side gallery Venus Over Manhattan is filled with bulletin boards. (Disclosure: Venus Over Manhattan is owned by Observer contributor Adam Lindemann.) The West Village alternative space White Columns, which has been home to a bulletin-board exhibition space for a number of years, gave bulletin boards to more than 20 artists and art types and asked them to present something with it.

The conceit could have produced one-liners, but there are quite a few strong pieces. Daniel Turner scrapped down and disfigured his cork board, leaving it empty except for some deep scars. B. Wurtz elegantly hung four socks on a stretch of canvas painted with the words "know thyself." Gavin Brown took photographs of the inside of a refrigerator and presented them inside one board's windows. And Bjarne Melgaard stuffed his with crumpled drawings, mail and at least one hypodermic needle—a bulletin board overflowing with information and harkening back to the creepy murderer-obsessed installation he staged in the bathroom of Luxembourg & Dayan a few months ago.

But our favorite board belongs to Darren Bader, who took perhaps the most resolutely minimal approach, offering a bulletin board in its most pure form. He hung just a single item with a pin, an odd little painting of something not quite safe for work happening in a bedroom. There's a caption in Spanish underneath it. Click the image to see it a bit closer and head to the show before Aug. 24 to see it.

Every Friday, Don’t Miss It! looks at a single artwork on view in New York.

(Courtesy Venus Over Manhattan)

After its dark, moody debut exhibition "À Rebours," which channeled the feel of a late-19th-century aristocrat's private chambers, the Venus Over Manhattan gallery is going in a comparatively contemporary and light-hearted direction for its sophomore effort. This outing is titled "Bulletin Boards," and it's being organized by West Village alternative space White Columns. (Full disclosure: VoM is owned by Observer contributor Adam Lindemann.)

For the show, Matthew Higgs, the director and chief curator of White Columns, has asked more than 20 artists and art types, including Rita Ackermann, Darren Bader, Gavin Brown, Margaret Lee and Michele Abeles, Bjarne Melgaard, Virginia Overton, Daniel Turner and B. Wurtz, to present work using a bulletin board. The show opens July 19.

"They range between a very literal take on the bulletin board to somebody who, as of right now, is going to turn one into a fish tank," a gallery representative told us by phone, adding, "It's nice to be bringing White Columns uptown." Proceeds from sales will benefit White Columns.

Since 2004, Mr. Higgs himself has operated a bulletin board as an exhibition space in the lobby of White Columns, and prior to arriving at the institution used one as a project space at the California College of the Arts, according to the gallery's release. For this affair, 20 participants will have 4-foot-by-3-foot boards and four people will have 6-foot-by-4-foot boards.

This announcement underscores what has been a strong season for bulletin board-related art. The very pleasurable Liam Gillick retrospective at CCS Bard's Hessel Museum of Art, in Annandale-on-Hudson, N.Y., is filled with bulletin boards, whose contents have been selected by a variety of students and luminaries (one whole gallery is lined with them and bears a Boetti map), and Pati Hertling has been hosting occasional events under the name Bulletin Board.

Nicole Maloof, Yale University School of Art, 'Monkey,' 2012 (Courtesy the artist and VIP MFA)

It’s late spring, time once again for the age-old tradition of the MFA thesis exhibition. Graduating art school students put on a final show of their work, in a rite of passage that marks the beginning of their lives as officially accredited artists, with all the struggles that entails: finding a studio, finding a gallery. The thesis shows, at least at the top-end schools like Columbia, Hunter and Yale, have also become a way for collectors and dealers to sniff out talent. It’s just a matter of making all those trips to all those schools. As of last week, there’s a brand new twist on the MFA thesis show, one that doesn’t involve any schlepping. VIP MFA, which launched last Friday, is the first-ever juried art fair that gives arts professionals and collectors a crack at the new talent emerging from 58 art schools around the world, from Manhattan to Mumbai—and it happens entirely online.

VIP MFA’s organizers are James and Jane Cohan, and Internet entrepreneurs Jonas and Alessandra Almgren, founders of the two-year-old VIP Art Fair. That fair hosts galleries, which pay for virtual booths in which visitors to the site can view artworks, along with their price ranges; prospective collectors buy work by calling the dealers, or using the fair’s customized chat function. A whopping 100,000 people from 155 countries have registered on VIP’s platform.

As for VIP MFA, there are limits to its comparison to a thesis exhibition; many of the students whose work is featured have yet to graduate, while others graduated in 2010 or 2011. Student work appearing at brick-and-mortar art fairs is pretty rare, but exhibitions of student work by commercial galleries is not unheard of. Back in 2006, when New York gallerist Jack Tilton held his “School Days” exhibition—a show of promising young talent from places like Hunter and Yale—the show, to some, exemplified an overheated, youth-obsessed art market with collectors tripping over each other to get to the MFA thesis exhibitions, clamoring to discover the next Warhol. It had critics and art professionals wondering if the practice was exploitative and harmful to the development of the downy art youth.

And yet, as brazen as “School Days” may have been, it really wasn’t anything especially new. And neither, in some respects, is VIP MFA. The general feeling among academics is that grad students, unlike undergrads, can fend for themselves.

“Dealers started to cannibalize MFA programs some years ago,” said Bruce Ferguson, former dean of Columbia’s School of the Arts and current dean of the School of Humanities and Social Sciences at the American University in Cairo. “MFA students know what the issues are and what the problems are. I don’t think they are innocent or being exploited.”

Even before putting on “School Days,” Mr. Tilton visited schools. “I would stick by the rules and wait for the MFA thesis shows, and [artists] would already be picked up. You have to get in early or you miss the boat.”

But VIP MFA’s platform allows purchases with the click of a single button, making it more effective than a thesis exhibition, or even a group show at a commercial gallery, at delivering student work directly into the hands of collectors.

Browse the site during the fair’s week-long run (it ends on June 8) and you’ll likely encounter the paintings of Chris Hood, a recent graduate of the San Francisco Institute of Art. A few of his works look polished, others amateurish. A large, Pop-inspired painting of a grid of 12 identical flowers in various shades of gray is one of the more clean, eye-grabbing works. It carried a reasonable (for today’s art market) price tag of $2,400. That, coupled with the ability to purchase it on the spot, probably made it candy for the impulse buyer. On the opening morning of the fair, its sale, along with a smaller painting of two hands clapping, was met with a celebratory Tweet from VIP MFA: “Chris Hood from SF Institute of Art 2 artworks SOLD.”

Acquisition of artwork at an art fair has never been so seamless, or so impersonal.

THE VIP ART FAIR has not exactly been an unmitigated success.

The first fair, in January 2011, was beset by technical difficulties that left dealers without the vaunted chat function. The site was temporarily shut down, and dealers couldn’t update the “back room” viewing function. The fair was reduced to something akin to an ordinary gallery website, and dealers, some of whom had paid around $20,000 for a booth, were not happy. In compensation, VIP offered partial refunds.

The second edition, which took place three months ago, was aided by an influx of $1 million by art collector Philip Keir and investor Selmo Nissenbaum. It ran smoothly and offered amenities like “insider tours” and videotaped discussions with dealers, but in terms of sales it doesn’t seem to have been much of an improvement. “The fair was unfortunately a waste of time for us this year,” dealer David Zwirner told Forbes. “We didn’t have any significant traffic in the booth, nor did we meet new collectors. I’m uncertain this format will work moving forward.”

VIP has spawned several spin-off ventures, such as VIP Paper (works on paper) and VIP Photo (fine art photography) and, now, VIP MFA, the purpose of which, Mr. Cohan explained, is to give artists exposure to a “broader public”—meaning “collectors, dealers and critics”—while also “serving our audience who are obsessed with contemporary art.” The average collector who visits the site is “not going to be your blue-chip Warhol buyer,” he explained. “It’s going to be someone who has a thirst for less-expensive, edgier work.” The most expensive piece is around $42,000; most of the work ranges from $400 to $10,000, far cheaper than the $500,000-and-up pricetags on a portion of the pieces on VIP (students split sales with VIP 50/50).

Not just anyone makes it onto VIP MFA. According to Gregorio Cámara, manager of VIP MFA, the fair approached administrators of the world’s top MFA programs and asked if they wanted to be involved. They could choose to either nominate students or have an open call. Even if school administrators were unreachable, or chose to not get involved, as was the case with Yale, Columbia and Goldsmiths in London, VIP MFA was not discouraged from spreading the word to students themselves.

In the end, the fair received applications from 380 students from 58 schools in 25 countries, with each student submitting up to 10 jpegs of artworks. Those were then submitted to the fair’s team of six judges, who selected 100 students to participate in the fair and chose three winners for a monetary award (Chris Hood got $10,000 for coming in second; first place was $15,000 and third $5,000) to be split with their schools. Whether or not a school would accept the money was a different story. Gregory Amenoff, chair of the visual arts department at Columbia University, said that had one of the participating Columbia students won, the university, which chose not to participate on the institutional level, would not have taken the money. “If someone’s lucky enough to get it, we’re going to turn the money over to the student,” he said, adding that his attitude toward any student who chose to participate in the fair was, “good luck, I hope they get the big goddamn award. And get a good studio and proceed with their life.”

If VIP Art Fair derives its legitimacy from the galleries that participate, VIP MFA gets it from its panel of judges, to whom the fair pays an undisclosed sum: all of them are esteemed figures in the art world. There is Matthew Higgs, director of New York alternative space White Columns; Kate Fowle, executive director of Independent Curators International (ICI); RoseLee Goldberg, founder and director of the Performa biennial; and Joachim Pissarro, an art history professor and director of the Hunter College Art Galleries. There are also two artists, O Zhang and Diana Al-Hadid. Jens Hoffmann, director of San Francisco’s CCA Wattis Institute for Contemporary Arts, was appointed a judge, but had to pull out due to his affiliation with another art fair, Art Basel.

“It’s not clear exactly what it is,” Mr. Higgs conceded, when asked about VIP MFA. “What happens now is the question.” He said his reason for getting involved “is the same reason White Columns participates as a not-for-profit in an art fair: Our hope is that we find an audience of people who were unaware of us before. So my optimistic goal for these artists, is that, like the five or six people on the panel, another five or six people might come across their work for the first time, and it might lead to a subsequent opportunity.”

That opportunity would mean a lot to today’s art school grads, who emerge into a dismal economy burdened with tens of thousands of dollars in student loan debt and little chance of finding a day job.

Then again, exposure isn’t necessarily what students, who are still developing their work, should be looking for. Instead, said Columbia’s Mr. Amenoff, they may need time to experiment and be free of the pressures of the art market.

Mr. Tilton sold about half the work in his 2006 “School Days” show, but only a handful of its artists have gallery representation today. “If you pick 10, and two to three stay on track, you’re doing great,” said Mr. Tilton, “Not a lot of artists make it big.”

Some of the show’s young artists, like Natalie Frank, Titus Kaphar and Keltie Ferris, made a splash at the time and have galleries, but the ensuing years haven’t necessarily been a smooth ride. We emailed Ms. Frank, whose upcoming solo show in October, at her new gallery, Fredericks and Freiser, will arrive a full six years after her last New York show. She explained that it was a “luxury and gift” to have the platform of the show at Tilton even at a time when she was still developing as an artist, but that she eventually needed to take some time to focus on her work. “I always saw the business of art as an entirely separate component from the art itself,” she said. “I think the studio and artist should be mindful to separate the two, and while keeping an eye on their interest in this transaction, protect the actual work from its influence. I don't know that it is for me to say whether young artists should take or not take a specific path.”

rjovanovic@observer.com

(Courtesy VIP)

As art students around the country and internationally are gearing up for their MFA thesis exhibitions, the VIP MFA Art Fair will give those same students a chance to join a juried online contemporary art fair. For one-week, from June 1-8, VIP MFA Art Fair, brought to you by the people behind the online fairs VIP Art Fair, VIP Paper and VIP Photo, will present an online event made just for graduate students and recent alums itching to make their first big splash in the art world, online. Why wait for a gallery to come to you? As its poster advertises, “Apply Now and Launch Yourself Into the Art World.”

Like a thesis exhibition, the selected artists will select a small body of work, in this case five to 10 works, and will get to show them to a curated audience. But rather than host the exhibition at the student’s school studio, this exhibition will make the works available through the VIP Art Fair platform, which boasts 73,000 registrants from 155 countries, including collectors, art dealers, curators and institutions.

VIP MFA, which is taking applications both by invitation and open submission, began inviting schools one week ago and has thus far already received more than 100 applications. There are 46 schools in total with programs in the U.K., Singapore, Egypt and South Africa, and 20 schools from the U.S. including Cal Arts, Columbia, SVA and Hunter. Additionally, there are 10 schools whose inclusion is pending. VIP MFA is open to including schools they haven’t had the opportunity to consider.

“A student emailed us from the School of Fine Arts in Athens,” said VIP MFA's Gregorio Cámara, “Now they are in the conversation.”

The fair will end submissions on May 6, at which point, a panel of six judges will decide which 200 students will participate. The judges are artists Diana Al-Hadid and O Zhang, Matthew Higgs of White Columns, Kate Fowle of ICI, Jens Hoffmann of Wattis Institute and Joachim Pissarro of Hunter College.

Of that pool of 200 artists, three “outstanding” artists will be selected to receive a prize, which will be split with their MFA institution ($15,000 for 1st place, $10,000 for 2nd place and $5,000 for 3rd place).

“It’s somewhat unruly, unmanageable, and unpredictable,” said Matthew Higgs, the director and chief curator of White Columns who has also served on the jury for the Turner Prize. “It’s very refreshing to see work this way, not through the usual channels and a preordained context.”

For Mr. Higgs, it’s not dissimilar from the open submissions policy of White Columns, New York's oldest alternative art space, which is responsible for giving many artists who would later be world-renowned their first exhibitions. While he said it can only be positive for the students, he noted some “complicated concerns” that the fair raises like “the speed at which art leaves the studio,” which he admits is nonetheless not a new issue for the art world.

With an audience of 73,000 viewers from the art industry, many of these artists will not have even had a chance to flounder a little. Maybe there’s no longer any room or time for floundering, only launching. What will come of this generation of artists, “The First Generation,” as the poster announces, “To Emerge Via the Internet” 10 years down the line?

Who knows? But for now, you too can take part because, like all work in the VIP Art Fair, these works will be for sale. Mr. Cámara expects the work to be in the range of $2,000-5,000, which is normal for an open studio or MFA exhibition, but he can’t say for sure. “We’re asking the students to appraise their own work.”

Mark Handforth's "Electric Tree."

Happy 10th, ABMB
Art Basel Miami Beach turned 10 this year. There is a lot of getting swept up in things at the fair and its ancillary activities—its many, many, many ancillary activities, like so many barnacles on a whale that the whale lists to the side, from satellite fairs to parties sponsored by Champagne companies and fashion companies and car companies.What can get lost in the shuffle is that there is still very good art to be seen in the convention center. Take the paintings by 79-year-old Joan Semmel at the booth of New York dealer Alexander Gray. There were Ms. Semmel’s sexy paintings from the early ’70s showing couples in flagrante and depicted from, as she will tell you, a woman’s perspective—which was a racier thing back then—and then there was the unflinching nude self-portrait she made just this year. Art Basel celebrated its birthday later in the week, with a series of performances co-organized with the Performa biennial. One was a comedy show. Reggie Watts, with voluminous Afro, took the stage. “Why does it have to be Your-ami?” he asked. Tell that to the bevy of car company-sponsored parties. —Sarah Douglas

Smoke, Strippers, Salem, Courtesy the Hole Gallery
On Wednesday night we saw the reliably dark and gothic band Salem, an art-world favorite in recent years, play outside at the Delano Hotel’s pool in Miami Beach, a party organized by former Deitch director Kathy Grayson’s Bowery gallery, the Hole. White smoke billowed across the stage as the band entered. Then two women in bikinis and heels arrived, and positioned themselves precariously close to the edge of the pool.

As a breeze picked up, the smell of marijuana passed through the crowd. And then the music started—crisp drum-machine clicks caterwauling one over another, piercing through thick waves of distorted, fuzzy drones. The women grabbed the pool’s poles and swung in place, shaking to the beat. The crowd, sitting on large white beds along the pools, reached for their cameras.

A while back, The New York Times declared one Salem show “the kind of performance that you have seen only in your worst dreams.” Wednesday night was also nightmarish, but sublimely so, the band’s woozy, drug-addled electronic-cut hip-hop befitting the middle of a week of frenetic Basel excess. Whatever live-performance problems they once had are now gone.

“First I tie your hands and feet,” lead singer Jack Donoghue rapped on “Sick,” sounding like a drug-addled Rick Ross trying to tread through swirling Cocteau Twins-style synths. “Shhh … / Don’t make a peep.” The women had by now shed their tops and fully entered the water. Across the pool, one gentleman waded in, beckoning for a lap dance. He got it.

Over on our side, a handful of guests—mostly women—slipped bills under the straps of one dancer’s bikini, as she slowly slinked down half the length of the pool, posing for photos, caressing herself. She moved toward the center, joining the other dancer and they writhed together in the water. Marina Abramovic’s recent Los Angeles MoCA gala-as-performance-artwork suddenly felt very quaint. —Andrew Russeth

Bringing Sexy Back
Here is something that should have worked and did: a portion of hedge funder Adam Sender’s art collection was installed in a house that he has vacated and is trying to sell. (Mr. Sender and his family now live down the block.) There were clever moments in the show: what had clearly been his young daughter’s room—the pink wallpaper was telling—had been infiltrated by a bunch of R-, or perhaps even X-rated artworks: a bejeweled-looking Raqib Shaw painting of a strange mythological figure gripping its serpentine phallus, a terrific Glenn Ligon text painting where the first line of text alluded to a certain group’s having “the biggest dicks in the world.” The house had other surprises that depended on its architecture for effect: a child’s shoe made of wax by Robert Gober perched in a cubbyhole; a rooster made of cigarettes by Sarah Lucas perched in a shower stall. The highlight of the installation was a group of wax figures by Urs Fischer that were set alight at their wicks and left to burn. These were positioned just inside the door of the home, an indication, right away, that things would be hot in here. —SD

Painting With Nas
Near the end of his set on Thursday night at Miami’s Ricochet Bar & Lounge, Nas acknowledged that he was in town during Art Basel, and announced that he was going to make an artwork on stage.

A white board was delivered, along with washable markers and a small set of paints. “Is this real paint?” the Queens-born rapper asked. “Water paints? I can do that shit too.” He picked up a paintbrush and made a red mark on the board. Then a gunshot tore through the speakers, and he launched into his 2002 hit “Made You Look.”

“They shooting, aw, made you look,” he growled, shots cracking behind him. “You a slave to a page in my rhyme book.” As he rapped, he worked the canvas, gently—a dab here, a dab there—taking his time, and then switched to marker.

“My shit looks really fucking stupid right now,” he declared as the song ended, examining his spare, abstract work.
The evening’s host suddenly suggested an auction, to benefit a children’s cancer charity. He explained that artist Rashid Johnson, who was perched on a banquette to the right of the stage, was willing to pay $5,000 for “the Nas original.” Who would pay more?

A hand shot up in the audience. “$6,000!”

Photographer and filmmaker Luis Gispert, sitting next to Mr. Johnson, wearing a sleek vest, threw his hand up, offering $10,000. Another bidder went in for $12,000. Mr. Johnson, who had been rapping along with Nas for most of the night, had some fight in him. He grinned, offered $14,000 and won.

One could not have made up that sight. But it had been that kind of evening. Before Nas’s set, women in white Big Mac T-shirts had circulated, offering the burgers, apparently because McDonald’s had helped sponsor the event. Before that, R&B phenom Theophilus London served as opener, plowing through his tracks, and then announcing he wanted to hear Jay-Z and Kanye West’s “Paris.” He danced with his band on stage, lip-synching the lyrics as the crowd of about 200 sang with him.

Accompanied by conga drummer Leon Mobley, Nas had performed “N.Y. State of Mind,” “If I Ruled the World,” “You Can Hate Me Now,” “Got Yourself a Gun” and half a dozen other of his hits. The crowd was in the palm of his hand. But he still seemed genuinely moved by Mr. Johnson’s gesture, pausing to thank him in front of the crowd.

“That’s the first time I’ve ever sold art in my life,” Nas said. “That shit made me feel good.” —AR

Getting The Swing Of It
Here is something that should not have worked but did: Nate Lowman’s bullet-hole paintings installed in a batting cage in Yankees power hitter Alex Rodriguez’s sprawling new bayside home sounded like a gimmicky idea in theory. In practice, so to speak, it was kind of brilliant. Mr. Lowman, with the help of adviser Jeanne Greenberg Rohatyn, had attached the paintings to the inside of the cage’s netting, so that they looked as though they’d been punctured not with bullets but with baseballs. Hanging on the walls surrounding the cage were Mr. Lowman’s smiley face paintings, the smiley faces transformed, in this setting, into spectators at the big game. A-Rod had a party to show off the installation, and it was attended by Mr. Lowman and the sundry artists in his downtown clique—Hanna Liden had collaborated on a work hanging in the ball player’s house—as well as dealers like David Zwirner and gallerist/curators like Alex Gartenfeld. A woman standing near the pool was heard to say, after gazing around at the assembled guests, “It’s nice that art can bring hipsters and jocks together.” —SD

Lit Up
But if it is a by-product of art that it brings people together, there was no better exemplar of this than the Electric Tree that artist Mark Handforth had created in the wilds of North Miami, far from the hubbub of the fair. Mr. Handforth, who was born in Hong Kong, raised in the U.K. and attended art school in London and Frankfurt, has lived in Miami since 1992, and has said he considers most all art to be public art. The warm glow of the fluorescent bulbs attached to the giant banyan tree in Griffing Park had a warm day-for-night effect, created an equalizing nimbus. Sotheby’s chief auctioneer Tobias Meyer, due later at some party for Ferrari, had made the trek, as had curator Matthew Higgs. But there were no art people and otherwise here, there was just a bunch of people bathed in green/yellow light, standing around, talking, drinking plastic flutes of Champagne, liking art. —SD

Billy Childish, "Toni Kurz Descending (Study 1)," 2011, oil and charcoal on linen, 59.8 x 36 inches. (Courtesy the artist and Lehmann Maupin Gallery)

“There are people who have said to me, ‘They’re not going to swallow you in the art world until you’re dead,’” the musician, poet, novelist and artist Billy Childish said. “The chance that it has been moved forward 20—or 30 years, hopefully—is something that I never expected.”

Mr. Childish, 51, was speaking on the phone from Chatham, England, where he was born and still lives, and he was discussing his upcoming painting show at the Lower East Side branch of the Lehmann Maupin gallery, which opens Nov. 4. He has had a handful of shows in Europe, but this exhibition will be his first at a commercial gallery in New York.

These days, many visual artists are multitaskers. They write, they make clothing, they work in multiple mediums; art’s expanded field has made experimentation and cross-disciplinary practice not just an attractive option, but de rigueur. Which makes Mr. Childish inadvertently prescient: he has been at it for years. Not that it’s been easy.

“Really creative people are not liked in literature, in art or in music,” he said. “They tend to be excluded, and the reason being that they’re not containable and they’re pains in the ass. I’m one of those people—uncontainable and a pain in the ass.”

What from all appearances has certainly been uncontainable is Mr. Childish’s output. Since the late 1970s, he has completed more than 2,000 paintings, published more than 50 books of poetry and written five novels. He has run a printing press and a record label, and he has played a supporting role in many of British contemporary art’s major events.

But he is best known as a musician. He has released more than 110 records with a variety of post-punk, blues-inflected bands since the late 1970s with monikers like the Pop Rivets, Thee Milkshakes, Thee Mighty Caesars, Thee Headcoats, the Musicians of the British Empire and the Buff Medways.

“In the 1990s, I think I must have seen Billy’s bands play more than 100 times,” British-born curator Matthew Higgs told The Observer, “and I will say without hesitation he was the best front man I have ever seen.” Mr. Higgs, 47, presented the artist’s work at the White Columns alternative space in the West Village, where he is director, and is curating the Lehmann Maupin exhibition.

“They wanted someone who has some history with me to try to tell this very big story without confusing people,” Mr. Childish said. He and Mr. Higgs have been friends since the early 1990s, when the painter Peter Doig introduced them. Messrs. Doig and Higgs co-curated a show of Mr. Childish’s work at London’s nonprofit Cubitt gallery in 1993, the very first show that Mr. Higgs ever produced.

“It was the first stirrings of the YBAs,” Mr. Higgs said, referring to the group known as the Young British Artists, who were gaining fame at the time. “The work Billy was making was very different.” As YBA Damien Hirst began making his first sculptures with live animals and carcasses—a 1990 work consisted of a white box in which maggots fed on a rotting cow head, eventually growing into flies—Mr. Childish was looking to painters of the late 19th and early 20th centuries.

That work, Mr. Higgs said, “was very influenced by German Expressionism. There was a very strong line; it was almost a painted version of woodcuts.” He painted pastoral scenes in long strokes and bright colors, recalling the work of Vincent van Gogh and Edvard Munch. Sometimes a silent solitary figure appears in these landscapes, wandering through them.

“Both Peter and I knew Billy’s music, art and writing,” Mr. Higgs told us, “but his painting simply wasn’t as well known.” And yet that had been the artist’s first passion. In his youth, he painted at home and often took trips to the museums in London, where he developed unfashionable tastes, leaning away from conceptual and abstract work. “I would look at the Rothkos, and I found them completely depressing and uninteresting,” he said.

After dropping out of school at 16 to work at a dockyard as a stonemason, Mr. Childish continued to draw, but, having no credentials, he had to fight his way into art school, first at a local college. “I was very unimpressed by art schools and art teachers telling me what to do,” he said. “I came from an educational background where we didn’t listen to teachers at all. We were just dockyard fodder.”

Even when he did manage to enroll at Saint Martins College, he remained an iconoclast. “I refused to paint inside the college,” he said. “I painted at home, and told them I did not want to be contaminated by painting in their building.” Not unpredictably, he was expelled. On the plus side, he met Mr. Doig. “We were into the same type of music, and he gave me—I’m looking at it right now on the shelf—it’s Bukowski’s Erections, Ejaculations, Exhibitions, and General Tales of Ordinary Madness. Pete said, ‘Oh you’ll like this.’”

At the time, Mr. Childish was already churning out material—drawing, printing, painting, writing and cutting records at a rapid pace—not unlike Bukowksi. “He’s not my favorite writer by a long shot,” he told us. “There’s a huge amount of work, and there’s a lot of it that isn’t that good, when he’s acting like a macho idiot, but there is a hell of a lot of it that is, and that bit is still more than a lot of people do in a couple of lifetimes. I realized in retrospect that I was doing the right thing.”

In the 1980s, Mr. Childish became involved with the artist Tracey Emin, who went on to become one of the progenitors of the YBA aesthetic, becoming best known for confessional work, like a camping tent in which she sewed the names of every person she’d ever slept with. (Mr. Childish was included.) She had been studying fashion at the time and worked with him on his printing press. After they split, they remained friends. “Tracey and I did not see eye to eye on Britart,” Mr. Childish said with good humor, using another name for the YBA's art. “I called it bankers’ Dada.”

On the phone, Mr. Childish is soft spoken and gracious, every bit the English gentleman. But he can be biting. He has a “primal, aggressive, antagonistic aesthetic,” Mr. Higgs said. He sings songs with titles like “I’ve Been Fucking Your Daughters and Pissing on Your Lawn” and “Get Out of Here Pretty Girl.” The lyrics of the latter announce, “I’m gonna put a sock in your mouth / and throw you out that door.” He often performs these songs dressed in a tweed blazer and bow tie, sometimes wearing a newsboy hat or a fedora.

He has also written acerbic diatribes about the state of contemporary art. In the mid-1990s, he wrote what he calls “very strong anti-art manifestos. They were very volatile, very contradictory, very sarcastic.” One manifesto, published in 1997, which railed against conceptual art, includes the dictums “Good taste is fascism” and “We must embrace the unacceptable in all spheres.”

Mr. Childish’s candidness, and his prolific output, which dealers frown on, did not help his art career; nor did joining with an old literary rival, Charles Thompson—“He used to try to have me banned from readings for being so outspoken and condescending about his work,” he explained—in the late 1990s to form a group called Stuckism, which devoted itself to painting and figuration, and aligned itself in opposition to the YBAs.

The name for the movement came from a poem by Mr. Childish in which he recounted Ms. Emin telling him, “Your paintings are stuck, you are stuck!”

“Charles Thompson had a big problem with Tracey at the time, because I think that she hadn’t made him a cup of tea when she went to go visit,” Mr. Childish told us. “She hadn’t been as welcoming as he thought she should have been.”

These days, the Stuckists tend to surface for half-baked protests surrounding festivities related to the Turner Prize, the annual art award that Tate bestows on one artist under 50, and which has often favored conceptual or abstract work. “I never attended any of the demonstrations, or condoned it,” Mr. Childish said. “I thought that they were overly concerned about what Britart represented, and I did not want to get into a reactionary situation of validating bankers’ Dada.”

He now says that he wanted to leave the group after its first exhibition in 1999, but stuck around for about a year and a half, formally resigning in 2001. Nevertheless, that short involvement, as well as his music background, has given him a reputation of an outsider.

“He is constantly being anachronistic,” Mr. Higgs told us. “Whatever he is doing, it seems to be wrong, and you have to have an extraordinary amount of self-confidence to believe in that.” Indeed, as cultural tastes have changed, Mr. Childish has kept working as he always has, churning out records, honing his painting and writing prodigiously.

“He comes in and out of focus in the culture,” Mr. Higgs said. As interests shift, people discover him and he becomes a star; other times he is forgotten. He added, “Now, more than 30 years after he started, we can see what a remarkable thing he set in motion as an 18 or 19 year old. His idea was fully formed at the beginning, and his life has really been fleshing out this idea.”

Mr. Childish’s painting has gradually evolved, and he has been working on a larger scale. “I paint a little less than I used to,” he said, “and I make a little less music, which is still too much. I’m trying to moderate myself.” His new works at Lehmann Maupin (which, by coincidence, also represents Ms. Emin) will include paintings of figures like the Finnish composer Sibelius and the German mountain climber Toni Kurz, who died tragically at the age of 23.

“I like this existential loneliness of people who go out into the void and do something,” Mr. Childish said. “The heroism of it; pitting yourself against yourself.”

Does he see himself in that role? “It’s not something that I want,” he replied. “I’m interested in it, but I don’t think that it’s the truth—I think it’s a very easily believed lie.”

But, Mr. Childish allowed, “Sibelius is a bit of a kindred spirit in the sense that he was a completely messed up, melancholic young man. He wrote his last symphony and decided it would never be quite good enough at age 60 and so he burned it and never wrote another thing and lived into his 90s.”

He thought for a moment.

“That’s almost the opposite of what I’m like,” he said. “But I don’t know. I’m not 60.”

arusseth@observer.com