If there is one thing about which the acquaintances of painter Chuck Connelly can agree, it is that Mr. Connelly is his own worst enemy. A successful and prolific artist in the 1980s, Mr. Connelly had a hotshot dealer, Annina Nosei. He had soon-to-be-idolized colleagues, Jean-Michel Basquiat and Julian Schnabel. And the press saw the potential of his Neo-Expressionist work: “Chuck Connelly is one of a number of promising artists intent on making ambitious paintings,” the New York Times wrote in 1985.

But after having alienated dealers, patrons, friends, and family with his egotism and alcoholism, Mr. Connelly left New York, the gallery scene, and his career behind. In the ’80s, Mr. Connelly sold more than $1 million worth of art. In recent years, his paintings have sold in online auctions for as little as $550 apiece.

Now, as the subject of an HBO documentary, “The Art of Failure: Chuck Connelly Not for Sale,” which makes its premiere Monday, and with a solo show now on view at DFN Gallery and a recent sister show at the National Arts Club, the artist is waging a vigorous attempt to revive his career. But the painter’s reckless tendencies have proven difficult to suppress, and even strenuous supporters of Mr. Connelly’s cause — including Mr. Connelly himself — have expressed skepticism that his talent and productivity can outweigh his brash behavior.

“It’s usually helpful if an artist will bring people [to an opening] who will want to buy all your paintings rather than drink all your beer,” the president of DFN Gallery, which now represents Mr. Connelly, Rick Davidman, said. “And Chuck would definitely fall into the latter category.”

Indeed, Mr. Connelly has already engaged in the kind of behavior that helped eject him from New York’s Contemporary art scene two decades ago. In a recent interview, he expressed displeasure at the show at DFN. “I don’t like the show. It’s such a mixed bag. It doesn’t flow for me. It doesn’t make any sense,” he said. “The one at the National Gallery looked alright,” he said, referring to the show at the National Arts Club. “It fit better.”

In the ’80s, such bald barbs were Mr. Connelly’s trademark. He fashioned an image as a loose-lipped firecracker, unable to filter his criticism to save his career. He bickered with Ms. Nosei, ridiculing her for making a profit on his work. And he made little effort to curb his partying ways. “Chuck was sort of a downtown legend,” Mr. Davidman said. “He got thrown out of every bar down there.”

In 1989, Martin Scorsese fashioned a character, played by Nick Nolte, in “New York Stories: Life Lessons” directly after Mr. Connelly, using Mr. Connelly’s canvases and shots of the artist’s hand making brushstrokes in the film. When the film made its premiere, the New York Post’s Page Six gossip column reported that Mr. Connelly had trashed Mr. Scorsese’s work, saying it was mediocre and “no ‘Raging Bull.'” “I thought the script was clichéd and mundane,” Mr. Connelly reportedly said.

Mr. Connelly’s criticism of the film may or may not have torpedoed his career, but soon after, his fortunes took an immediate downturn. He did not have a major solo show after 1990.

Now, despite the fact that Mr. Connelly appears eager to resuscitate his career — for reasons of finance, artistic expression, or some combination of the two — he is again willing to bite the hand that could potentially feed him. He has expressed general dissatisfaction with his representation by DFN. “If I had my choice, I wouldn’t have gone there,” Mr. Connelly said.

And despite bartering paintings for assistance with his taxes, saying “I’d rather use up my talent than my cash,” he has also inhibited the presentation and sale of his work. While the curator of the show at the National Arts Club, Chrissy Crawford, spoke favorably of her interactions with the artist, saying “He’s a total mess, but he’s really sweet,” she also acknowledged difficulties in convincing Mr. Connelly to part with some of his work, particularly his older works, despite his dire financial situation.

“Just to get him to put a price on those to sell them for the DFN show was extremely difficult,” Ms. Crawford said. “Alternatively, they were just rotting in the basement.”

Many of Mr. Connelly’s canvases were, in fact, in a state of decay when Ms. Crawford visited the artist’s home in Pennsylvania to cull works from the approximately 3,500 paintings he was storing in his house. “There’s been a couple of floods, and I don’t even think there’s air conditioning in the house,” she said. “We went through the attic, basement, bedrooms, porch; he’s a paintaholic. He’ll have four or five canvases going at one time and he can flow between them.”

But both Mr. Davidman and Ms. Crawford said the current proclivities of the art market may mean that Mr. Connelly’s career flourishes in spite of himself, suggesting that his saturated, paint-heavy canvases may be back in vogue. “Part of the reason his career had a downturn is because he can be a pain in the butt, but also because the style of painting went toward an ironic, flat style in the ’90s,” Mr. Davidman said.

“It seems like painterly oil-on-canvas is having a resurgence,” Ms. Crawford said. “Art is at a point where it’s ready for Chuck again.”

Still, while art may be ready for him, he may not be ready for it. While DFN has sold seven of Mr. Connelly’s paintings, “He has blown sales,” Mr. Davidman said pointedly.

“There were clients who were interested in buying his work and wanted to meet him and wanted to find out what he was thinking when he did something. And Chuck will just say, ‘Buy the painting and leave me alone.'”