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Pruitt has been driving around for the past several weeks with a large stuffed panda in the back seat of his white Toyota Prius. The panda has seen better days — Pruitt found it on the side of the road five years ago on the way to his house in Montauk, where he has spent summers and many weekends since 2004 with his partner, the artist Jonathan Horowitz. Four toy panda cubs are in a box in the trunk. "I’ve been taking pictures of them in different poses," Pruitt says.

He has been transporting the pandas to different locations, including Montauk and his studio in Brooklyn, on an industrial street near the Brooklyn-Queens Expressway. On a Sunday in January, Pruitt sits crossed-legged on the floor of his studio.

He’s trying to prop the ear of a small panda under the nose of the larger one so that they stay balanced long enough for him to snap some photos with his iPhone.

Pruitt himself is oddly adorable. He is softly silly in his mannerisms — every once in a while he twirls strands of his salt-and-pepper hair or pulls a chunk of bangs down over his right eye. Over dinner at a Japanese restaurant in downtown Manhattan near his longtime gallery, Gavin Browns Enterprise, he suggests ordering dishes to share and refuses the larger or last piece of anything. He shows up for a studio visit with oatmeal cookies and coffee for two. His work is similarly rooted in gestures of intimacy and sharing. He has made art out of anything and everything: pictures of pandas, old blue jeans, images of Paris Hilton, Marimekko prints, glitter, iPhotos — with which he has plastered Gavin Brown’s gallery, both inside and out — even real estate. He infuses quotidian objects and concepts with a seductive sense of community spiked with irreverence and humor. In his actions and words, he comes across as conscientious and generous (Max Brown, Gavin’s son and Pruitt’s godson, compares his voice to a monk’s), but his narrow dark-brown eyes reveal a poignant reticence.

For nearly 20 years Pruitt has traversed the rocky terrain of taste, perception, and criticism and emerged a beloved underdog. For seven of those years, he lived in self-imposed exile after the debacle of "Red, Black, Green, Red, White, and Blue," the 1992 blacksploitation show he mounted with his then partner, Jack Early, at the Leo Castelli Gallery. It was "probably the most reviled, the most embarrassing, and the most disastrous exhibition in the history of the downtown art world," states Jeffrey Deitch, the New York dealer recently appointed director of the Museum of Contemporary Art in Los Angeles, in Pop Touched Me: The Art of Rob Pruitt, the artist’s monograph, released last month by Abrams.

The show marked the end of the Pruitt-Early team and a nadir in both artists’ reputations and finances. But it also marked the beginning of Pruitt’s gradual reemergence as an individual artist, which culminated some six years later in Cocaine Buffet, 1998, a 40-foot-long Minimalist-inspired floor sculpture that invited the art world to get down on its knees and partake in a communal line of blow. He followed this with the 1999 solo exhibition "101 Art Ideas You Can Do Yourself" at Gavin Brown, which included simple suggestions like "make a painting on a lampshade," "spend the day in a costume," and "make up brand names." Since then Pruitt has become a master at presenting readily available material in an evocative context, mixing association and ambiguity. Last October’s "Rob Pruitt Presents the First Annual Art Awards" at the Guggenheim was one of the most talked-about art events in recent years. The spectacle, which also functioned as a fund-raiser for the museum, was hosted by Pruitt and the art-performance trio Delusional Downtown Divas. Even participants wondered what to make of it: Was it a sly critique of the art world’s hierarchies and market orientation, a conceptual stunt, a self-congratulatory party for insiders, a sincere tribute? Or was it all those things in one fantastic send-up? Artist-of-the-year Mary Heilmann commented: "I love that it’s important and serious and deep and cheesy at the same time."

The awards show highlighted the talent for showmanship that has made Pruitt one of the art world’s favorite ringmasters. In 2007 he donned a panda costume to host a flea market in Brown’s booth at the Frieze Art Fair, in London, purveying reasonably priced merchandise, like $2 rubber stamps designed by Yoko Ono. The enterprise played on the fair’s commercialism while fostering a homey feeling by transforming the space into a bohemian hangout where a fashion show or performance piece could happen at any moment.

Late last year, as part of the exhibition "Pop Life," the Tate Modern turned over its Turbine Hall to another of Pruitt’s flea markets; it also restaged "Red, Black, Green, Red, White, and Blue." The installation — a superheated assemblage of images of black icons like Michael Jackson, Michael Jordan, Martin Luther King Jr., and Malcolm X, with a rap soundtrack produced by Pruitt and Early — hadn’t been seen since 1992. "I didn’t really want it to be shown at the Tate," Pruitt says. "I just didn’t want to relive the whole thing again." But sensibilities had changed, and there was no critical outrage. The piece now looks tame to Pruitt. "I think it was a victim of the climate of the time," he says. "The work that was important at that moment was identity-issue work, which meant that if you were two white gay males, you should make work about being white and gay. The exhibition fell outside of that in a way that affronted some people."

Pruitt was born in 1964 in Washington, D.C., and grew up in suburban Rockville, Maryland. His mother and father were teenagers when they had him, and he suspects he was an accident. Neither parent had what he would call a career. His mother, now a caterer, was somehow involved in designing one of the first food courts in D.C. He’s not sure if his father, who died two years ago of cancer, finished high school, but Pruitt knows he never went to college. "My childhood was formed by having these two parents that were like an older brother and an older sister," he says. Pruitt remembers his mother showing up in his kindergarten classroom wearing micro-miniskirts and halter tops. As for his father, with whom he had a complicated yet influential relationship, "he pretty much stayed 19 years old his entire life."

Pruitt attended a progressive elementary school where he called the teachers by their first names. Every Friday the students all wore IALAC (for "I am lovable and capable") T-shirts. Pruitt and his family lived minutes from downtown D.C., and when China gave the giant pandas Hsing-Hsing and Ling-Ling to the National Zoo in 1972, the eight-year-old Pruitt became obsessed. "Most people go to the zoo maybe once a year," he says. "I went like once a month." By the time he was in high school, he was dressing like one of the Ramones and listening to Blondie while his preppy classmates were tuning in to Billy Joel. He also struggled in AP classes (he suspects he has undiagnosed dyslexia). At 15 he was subscribing to Interview magazine, and when Andy Warhol visited a local bookstore, Pruitt lined up to have him sign a shopping bag full of Brillo boxes and Campbell’s soup cans.

In 1981, Pruitt enrolled in the Corcoran College of Art and Design, in D.C., where he became friends with the admissions director, Tim Gunn (now of Project Runway fame). The following year Gunn left for Parsons the New School for Design, and Pruitt followed, aided by the $2 million his father had just won in the Maryland State Lottery (which also led to the elder Pruitt divorcing his wife, marrying a woman younger than his children, and buying a couple of Corvettes). In New York, Pruitt moved into the Chelsea Hotel. He credits his roommate there — a free spirit who made up for a lack of wardrobe by stealing a new outfit from the Salvation Army every day and donating her loot from the day before — with teaching him the ease of artmaking.

One of his works at Parsons involved filling hundreds of Ziploc bags with water and stapling them to a wall or lining a staircase with them — the latter a precursor of Pruitt’s Viagra Falls, featured in a group show at Tony Shafrazi two years ago. But Pruitt wasn’t particularly engaged as a student, preferring nightclubs and art shows in SoHo and the East Village to classes. "I think I had a huge ego," he says. In the late 1980s he started looking for a gallery job. When he inquired at Sonnabend, he was hired on the spot.

In 1990, 303 Gallery gave Pruitt and Early, his first boyfriend, their inaugural exhibition, "Artwork for Teenage Boys," a collection of misogynist cultural ephemera like bumper stickers and T-shirt iron ons plastered on Pabst beer cans. The show was so successful that Pruitt went from making $9 an hour to pulling in six figures. The venerable Leo Castelli, Ileana Sonnabends ex-husband, offered to mount the pair’s next outing. They decided to tackle racial-identity issues. Thinking back on that decision, Pruitt says, "If you’ve never failed before, it’s hard to imagine that you’re going to."

All the works in "Red, Black, Green, Red, White, and Blue" sold within a week, but the critical reaction was scathing. "The problems with the show weren’t really evident on opening night," says Pruitt. "But then suddenly it was like this crisis that needed to be dealt with. It was like a war room was assembled, and people sat at the table to figure out how to deal with it: Should we close the show? Should a public apology be issued?"

Pruitt likes to think that Sonnabend would have offered him his job back at the gallery if he hadn’t gone into hiding. "I felt guilty that I had hurt some people, even if it was inadvertent," he says. "I can say all I want that it was not my intention to make a racist gesture, but if it had that effect on some people, then there is a certain truth to that situation, and I felt like I had to take responsibility for it." To make ends meet, he took a series of odd jobs — coming up with craft ideas for Martha Stewart Living magazine and working at Anna Suis boutique in SoHo.

Meanwhile, he kept making art and exhibited in some low-profile group shows. He didn’t have a solo show, however, until 1999. Gavin Brown, whom Pruitt had known since Brown was an assistant at 303 Gallery, needed to fill an opening in his schedule quickly and approached the artist about making an exhibition out of the dozens of art ideas he had pinned on index cards around his studio. Pruitt agreed and pretty quickly decided that there should be 101 of them.

Around this time, Pruitt met Jonathan Horowitz. Pruitt had seen a show at White Columns, in New York, of the artist’s pieces — one of which, Pruitt recalls, consisted of a TV monitor and a box set of videos with a title card reading "Movies that made me cry" — and introduced himself then or shortly after. The two have been together ever since. In 2001, Pruitt and Horowitz purchased an 11-bedroom Victorian house in Fleischmanns, New York, and turned it into Peacock Hill, a goth-inspired domestic-art installation/public sculpture/tourist attraction where they hosted open weekends featuring such events as a Botox party, lawn chess, and tarot readings. They sold the house in 2004 to one of Al Gores presidential-campaign organizers.

Shortly after meeting Horowitz, Pruitt returned to his childhood obsession, the panda, with which he is now most prominently identified. "I had a mission to get people to like me again," says Pruitt. "Primarily, I was thinking that everyone loves pandas, so if I align myself with them, everyone will love me." Pruitt was also attracted to the bears as visual cues, equal parts black and white and thus symbolizing harmony between the races. One of his glitter panda paintings appears on the cover of the monograph Pop Touched Me, which brings together Pruitt’s works with comments on his career and influence from artists, dealers, curators, critics, and collectors. "Most of these I wrote myself," Pruitt deadpans. "I only wrote one of them myself, but I’m not going to tell you which one." He reads Jeff Koonss quote aloud: "I’ve always loved Rob’s work. It’s always been bright, fresh, engaging, and thoughtful."

Whether propagating culturally relevant iconography with provocative yet often tender ambivalence or whipping up art world happenings, Pruitt makes the act of creation seem enviably easy. For his show at the Galleria Franco Noero, in Turin through April 24, he created iPaintings using an iPhone app that his nephew introduced him to at Christmas. He embraces art as irrevocably linked to life — Daddy, 2008, a plastic Corvette on top of a painted wooden box, contains his father’s ashes. He dismisses, however, any suggestions that artmaking for him is reward enough. "I’ve always wanted to be famous," Pruitt says with a chuckle, "but I’ve also always thought that I had enough talent to warrant it."

"Stuck on You" originally appeared in the April 2010 issue of Art+Auction. For a complete list of articles from this issue available on ARTINFO, see Art+Auction's April 2010 Table of Contents.