In a recent Frieze article, the editors, trying to decide on the most important artist of the past decade, tossed around a number of names. The list included O.W.A.s, or Older Women Artists, recognized after years of neglect; it had Njideka Akunyili Crosby, an artist of the African diaspora, and Olafur Eliasson, who heralded the rise of immersive works conducive to selfies. The editors, somewhat reluctantly, also discussed Jordan Wolfson, a thirty-nine-year-old sculptor whose work is emblematic of a chaotic, maddening, fearful time.

Wolfson is best known for the interactive animatronic pieces that he makes in collaboration with a Hollywood creature-effects studio in Glendale, California. His creations are uncanny, mashed-up not-quite-humans, which perform “scenes” and deliver lines that Wolfson writes, often accompanied by a pop-music score. Like memes turned loose from the laboratory of the Internet, they engage with the audience in unsettling ways, delivering contradictory and controversial messages.

“Female Figure,” which débuted at David Zwirner’s New York gallery in 2014, is a silicone-skinned simulacrum of a woman, besmirched with dirt, in a platinum-blond wig, a white stripper outfit, and a beaky green-black witch mask. After delivering a monologue—“I’m gay / I’d like to be a poet”—spoken by Wolfson, who is straight, the figure, which is transfixed through the diaphragm by a metal pole connected to a mirror, begins to dance. While it vogues and twerks, a tiny camera hidden behind the mask, equipped with facial-recognition software, allows the figure to lock eyes with the spectator and, via the mirror, with itself. Did the piece express misogyny, or a criticism of it? Homophobia? A veiled confession? It was impossible to say for sure; Wolfson’s medium is plausible deniability. One Frieze editor said, “The politics were all wrong, yet no one could look away.”

Wolfson, who moves between New York and Los Angeles, has succeeded in creating event art that people, many of whom don’t typically go to galleries, line up to see. An instinct for controversy helps. “Annoyingness is an interesting strategy in art-making,” David Zwirner told me. “If you’re annoyed, you’re not indifferent. The work manipulates me, so I’m being triggered. Transgression is key. The only way to know you’re succeeding is if people are upset.” The outraged responses, he says, are a dimension of the art.

Wolfson’s work is owned by cultural institutions and private collections throughout the United States, Europe, and Asia. The Stedelijk Museum, in Amsterdam, presented a two-part Wolfson retrospective in 2016 and 2017; next year, he’ll take over the Kunsthaus Bregenz, the most important contemporary-art museum in Austria. Supporters of the work see it as a melancholy commentary on a lonely, mutually enslaved machine future, and a reflection of the caustic cruelty of humans. “There is a feeling of something untethered to aesthetic values such as we know them, things like good taste,” the painter David Salle told me. “I feel someone going direct, taking the germ of an idea and running with it in an uncensored way that might only be available to an artist in their youth, where self-criticality hasn’t kicked in.”

Detractors, of whom there are many, interpret Wolfson’s work as a noxious expression of privilege, casually appropriating pain he seems unlikely to have experienced personally. In a field that prides itself on openness to transgression and cheek, he has attracted unusually pointed criticism. “Who Likes Jordan Wolfson?” a recent essayist asked, summing up his artistic formula as “technically virtuosic production + shock + destabilizing juxtaposition + empty, judgment-less vision.”

The work is complicated by the matter of Wolfson’s personality, which ranges from syrupy, self-absorbed entitlement when he is feeling good to viciousness when he is not, with intermittent considerateness and situational charm. “One could describe Jordan in the most unflattering way possible, and it would be true, but none of it bothers me,” Salle said. “You can be an extravagant narcissist and a nice, well-bred young man at the same time.” Wolfson’s closest friend, an artist named Joey Frank, told me that, in an astrology class he teaches, he lectures on Wolfson as the quintessential Libra. When I asked him what that meant, Frank replied, “How do you drown a Libra? You put a mirror at the bottom of a swimming pool.”

Like the Internet, which is Wolfson’s greatest source and muse, his work can be both inflammatory and affectless. He refuses to make his intentions clear: pursuing meaning in the work is like stumbling through a mirrored maze. One New York collector told me that he considers Wolfson to be the perfect manifestation of the nastiest impulses of online life. “Like Keith Haring and Kenny Scharf in the eighties embodied street-art culture, that’s what he is with Internet trolling,” he said. The question, he added, is: “How in control of it is he?”

The first time I met Wolfson, three years ago in May, he asked me to pick him up at Los Angeles International Airport. When I got there and called to arrange a rendezvous, he told me to circle while he went to another terminal. His new girlfriend, Charlotte Day-Reiss, happened to be arriving on a different flight at the same time, and he wanted to plant a love note for her near her gate: a test of proficiency in the thought patterns of Jordan Wolfson.

Wolfson is pale, with dark, tousled hair, and full lips that he pooches out to Zoolander effect. He is both overly familiar and eerily oblivious. Getting in the car, wearing a hot-pink Wolfgang Tillmans T-shirt and a pair of track pants, he immediately apologized for his shoes, high-fashion sneakers covered in fake graffiti which, in the company of a note-taker, embarrassed him. “This is the first time I’ve ever worn them, and it’s a little much,” he said. “They’ll be good dirty.”

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He called Day-Reiss to see if she had found the note—she had—and to issue an invitation to join us for lunch, which she declined. “Even me asking my friend to come, if anything, it shows a little character weakness on my part,” he said, performing introspection. He promised I could talk to Day-Reiss “if she became important,” and asked me to drive him to a vegan restaurant. He mentioned that he has a daily exercise and meditation routine, and, in what would be the first of many times, he told me that I should get a Tesla. Last year, instead of a holiday gift, he asked David Zwirner to offset his annual carbon footprint, and he posted the certificate on Instagram.

In art, though, Wolfson professes disdain for virtue-signalling and political correctness. His hope is to make uncensored work that honors his intuition above all else: whatever pops into his brain, followed by tedious years of sorting out technical and production details with a team of collaborators. On the plane, he had sketched a new animatronic sculpture. “It’s been in my head for so long, and I actually fleshed it out on my drawing pad,” he said. After lunch, we stood by my car on a busy street, as he flipped through the pages of a black hardcover sketchbook, past notes for a piece involving a biker jacket painted with a swastika, before arriving at a drawing of a box with articulated arms and hands, suspended by a length of chain from a robotic arm used in car manufacturing. He was calling it the Cube, a “body sculpture” that would engage the viewer’s physical self.