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Finishing up one of the artworks for his exhibition. All depict male figures, often set against street scenes.Kayla Reefer for The New York Times

LOS ANGELES — If you asked the auteur film director Gus Van Sant how long he has been painting, he might tell you about winning first prize at the annual art show in his hometown Darien, Conn., when he was 12. He might relate the influence of Jackson Pollock on his style as an 8-year-old. (It wasn’t such a big deal, he’d say. “It was really just because you could throw paint and that was a painting.”) He might even explain how, as a dual painting and film major at the Rhode Island School of Design, he dropped the art course because film “was harder, and I just didn’t know about it. I knew about painting.”

He is not bragging, merely stating facts. On the day we meet at his modest hillside home in Los Angeles, Mr. Van Sant wears a black Diamond Supply Co. skate T-shirt tucked into loose indigo Levis and pads around shoeless. Breakfasting on takeout Denny’s pancakes and eggs at his kitchen counter, he is clearly aiming to impress no one.

Mr. Van Sant, 66, has always seemed indifferent to conventional standards of Hollywood success and acclaim. Setting out with an interest in experimental avant-garde films, he made his name in the late 1980s with the art-house film “Drugstore Cowboy,” following it in 1991 with “My Own Private Idaho.” Both are now considered classics of their genre.

After his 1997 feel-good movie “Good Will Hunting” was a surprise commercial success and garnered more than a dozen awards, including two Oscars, he responded to the carte blanche offered to him by Universal Studios by making a shot-for-shot color remake of Alfred Hitchcock’s “Psycho.” Unsurprisingly, it fared less well.

I am here to see some of the new paintings that Mr. Van Sant will exhibit beginning Sept. 12 at the Vito Schnabel Gallery in Greenwich Village. Titled “Recent Paintings, Hollywood Boulevard,” it will be his debut solo in New York, and the first time this new series will be shown in public.

The five examples leaning against a wall outside his home studio are waiting to be sealed. Done in ethereal, seeping watercolor directly on raw linen, the surfaces of these large paintings — all seven feet tall — are delicate, both aesthetically and materially.

All depict nude, male figures, often set against street scenes, climbing on top of cars, or, in a couple of surreal canvases, enlarged to giant proportions and striding over rooftops. Some include local landmarks like the Capitol Records building and the Griffith Observatory, of which Mr. Van Sant has a magnificent view from the deck where he usually paints.

The pictures evoke — though do not directly represent — the kinds of sad public spectacle that is all too commonly witnessed in Los Angeles, where a worsening homeless crisis brings with it the associated problems of untreated mental illness and drug addiction. The entertainment industry’s pull on fragile young hopefuls from across the world adds to this combustible social mix.

Mr. Van Sant tells me about a good-looking young man who sometimes stands naked at a busy intersection near the director’s home in Los Feliz, “looking at the traffic like he wants to kill it.” (The director only spotted him when this series of paintings was well underway.) A few days after we meet, I see on social media photographs of another man, apparently gripped by some kind of psychotic episode, clambering naked onto a parked car in the Silver Lake neighborhood. The photographs uncannily resemble a scene dreamed months earlier by Mr. Van Sant in his painting “Untitled (Hollywood 7).”

Mr. Van Sant’s paintings, in a palette that ranges from pastel to acid, have none of the tonal darkness of social documentary. His friend, the artist Paul McCarthy, observes that Mr. Van Sant’s work comes from a position of “acceptance and empathy.” As with “Drugstore Cowboy” and “My Own Private Idaho” ­— films about drug addicts and gay street hustlers — his pictures are nonjudgmental of their subjects, and suffused with affection, even erotic desire.

Early in his career, Mr. Van Sant, who is gay, rose to prominence as an exponent of the New Queer Cinema, and he has spoken frequently about his close artistic relationships with his actors, in particular with River Phoenix, who died of a drug overdose in 1993. The figures in his new paintings, he says, are mainly drawn from his imagination, but two are based on a young friend whom he describes as his current “muse.” Others, he says, are inspired by the design of the Oscar statuette, or by the Red Hot Chili Peppers’ predilection for performing in the buff.

No one should confuse the soft-spoken painter with the wild characters in his films and paintings. “Artists are not necessarily the performers,” he says. “They’re industrious. They adhere to rules, and they actually work.” As an example, he points to Jack Kerouac’s relationship with his muse, Neal Cassady: “Kerouac is disciplined and Neal Cassady is the freak, driving him around and partying.” Artists, Mr. Van Sant says, are often “attracted to the characters that seem to be freer than they are.”

While he has always painted, on and off, he began working in earnest in 2011 when he was asked to contribute to an exhibition instigated by the actor James Franco at the Gagosian gallery in Beverly Hills. (Mr. Franco appeared in Mr. Van Sant’s 2008 biopic, “Milk.”) The gallery, Mr. Van Sant says, “wanted to have something to sell.”

He retreated to a studio he had recently built on his property on Sauvie Island, off Portland, where he completed eight large watercolors on paper of the model Ash Stymest (another muse, though at the time they had not met) from photographs found in magazines. Since then, he has experimented with various styles, including geometric abstraction, photographic appropriation and screen-printing (“eight years of not complete failure but failing,” he says), but it’s the Stymest portraits that most obviously prefigure the “Hollywood Boulevard” series.

The gallerist Vito Schnabel, son of another prominent filmmaker-artist, Julian Schnabel, sees the paintings as “a kind of crazy psychedelic walk through Gus’s time in California.” The colors, he says, remind him of Chagall and Matisse. When he bumped into Van Sant at an Oscar party in 2018, the director showed him some paintings on his iPhone. Mr. Schnabel arranged a studio visit the very next day, and promptly offered him an exhibition.

I ask Mr. Van Sant if this new artistic focus means he has stopped making films. “I don’t know,” he answers. Then, a beat later, he tells me about a “great, inspirational idea” he had that very morning for a script. (These days he prefers to direct films based on scripts he himself has written.)

Mr. Van Sant has directed 18 features, including the well-received “Don’t Worry, He Won’t Get Far on Foot” from 2018, starring Joaquin Phoenix as the disabled Portland cartoonist John Callahan. “I kind of get tired sometimes,” he says. “Especially the way I make films.”

Where does visual art stand in relation to cinema, in his eyes? Is one art form more consequential than the other? “I always feel that filmmaking is a little less perfect,” he answers. “Whereas the painting and the literature worlds have been perfected.” To be enslaved to the conventions of narrative, or to the expectations and demands of financial backers, can be frustrating.

While Portland remains the city with which Mr. Van Sant is usually associated (and where many of his films are set), he moved to Los Angeles three years ago. Reluctantly, he has come to accept that he likes it.

“It feels as if there’s a strange vibe from something that’s not necessarily connected to humans,” he says. “Some geologic aberration that makes you feel uptight. You sort of feel anxious even when there’s absolutely nothing to do.
 
When he wakes up in the morning, he continues, there is always a moment when he as ks himself if he likes it here; usually, he decides  that he does. (‘‘You don’t get that in other places,” he says).

A similar  anxiety unsettles Mr. Van Sant’s paintings, although  their unthreatening pastel palette and miasmic drifts of gentle brush  strokes leave you wondering what, here, really, is  not  to like?