It’s one of the most intriguing—and head-scratching—friendships in recent art history. Today, Jean-Michel Basquiat and Andy Warhol are seen as two of the most innovative, influential artists of the late 20th century. Their works sell for tens of millions of dollars, routinely breaking auction records.

But in the early 1980s, they were an art-world mismatch. Basquiat was a smart, scruffy, charismatic graffiti artist of Haitian and Puerto Rican descent making waves in New York’s edgy downtown art scene. Warhol was a global celebrity and an icon of Pop Art—the 1960s movement that had upended ideas about art by ditching high-culture subjects for everyday stuff like Campbell’s soup cans. Basquiat, barely out of his teens, was just launching. Warhol, in his mid-50s, was seen by some as coasting.

How did these two artists develop not just a friendship but an energizing, dynamic collaboration that produced more than 150 works?

You might say it began with lunch. On October 4, 1982, Warhol had a lunch meeting at his studio—known famously in the New York art world as “the Factory”—with his dealer, Bruno Bischofberger. Bischofberger brought along a young artist he’d begun working with: Basquiat.

Warhol vaguely knew the young Black artist from the downtown art scene. “He’s the kid who used the name ‘Samo’ when he used to sit on the sidewalk in Greenwich Village and paint T-shirts, and I’d give him $10 here and there,” Warhol noted in his diary. “He was just one of those kids who drove me crazy.”

Bischofberger had arranged for Warhol to do portraits of new artists he was working with, in exchange for Warhol getting one of the artist’s works. That afternoon, Warhol took Polaroids of Basquiat in preparation for a quick silkscreen portrait. But Basquiat “one-upped him instantly,” wrote Warhol biographer Blake Gopnik. Instead of staying for lunch, Basquiat raced off with a Polaroid of himself and Warhol. As Warhol recounted in his diary, “within two hours a painting was back, still wet, of him and me together.” According to Bischofberger, Warhol was impressed. “I’m really jealous,” the dealer recalled Warhol saying. “He is faster than me.”

Not just faster. Basquiat’s highly original works—studded with symbols, words and vibrant color, brushed and marked with an almost feverish intensity—were gaining art-world traction. He’d had solo gallery shows in Italy, New York and Los Angeles, and that summer he’d been the youngest artist in the prestigious international exhibition Documenta. Bischofberger initiated the collaboration, bringing in a third artist, Francesco Clemente. When the trio finished their 15 commissioned pieces, Basquiat and Warhol continued together on their own.

Even though Warhol had long inspired Basquiat as an artist, thinker and cultural influence, the younger artist approached the collaboration as a creative equal. “Painting with Jean-Michel was not easy,” recalled artist Keith Haring, a downtown contemporary of Basquiat’s. “You had to forget any preconceived ideas of ownership and be prepared to have anything you’d done completely painted over within seconds.” Warhol found the challenge stimulating. “Andy loved the energy with which Jean would totally eradicate one image and enhance another,” Haring said.

“Jean-Michel got me into painting differently,” Warhol wrote.

The two became friends. As Haring described it, they “exercised together, ate together and laughed together.” But to other observers, the relationship seemed mutually exploitive, almost cynical. “It was like some crazy art-world marriage, and they were the odd couple,” said artist and Warhol assistant Ronnie Cutrone. “Jean-Michel thought he needed Andy's fame, and Andy thought he needed Jean-Michel's new blood. Jean-Michel gave Andy a rebellious image again.”

There was more to it than that. As Basquiat’s career took off, Warhol became almost a paternal figure to the younger man, who had left home at 17. In 1983, Warhol started renting him the Lower Manhattan building that became his home and studio. As Basquiat struggled with his growing success, binge-spending on designer clothes, lush parties and potent drugs, the older artist was often a steadying presence. Warhol actively discouraged his drug use and counseled him to retain his early paintings as a kind of nest egg to sell later.

Though sometimes exasperated by Basquiat’s erratic habits, Warhol was genuinely impressed by his art. “Jean-Michel came over to the office to paint but he fell asleep on the floor,” Warhol recorded in late 1984. “He looked like a bum lying there. But I woke him up and he did two masterpieces that were great.”

Basquiat got Warhol interested in painting by hand after more than 20 years of using the more mechanical silkscreen printing process. “Andy would start one and put something very recognizable on it, or a product logo, and I would sort of deface it,” Basquiat recalled. “Then I would try to get him to work some more on it. I would try to get him to do at least two things.” In some works, like “Sweet Pungent” (1984-85), Basquiat would make the first contribution, at times using Warhol’s silkscreen technique to reproduce his own line-drawn sketches.

Basquiat’s own paintings often raised themes of racial inequity and oppression—from colonialism to police brutality—and that messaging comes through in some collaborative works as well. Warhol began “Arm and Hammer II” (1985) by painting two versions of the well-known detergent logo side by side. Basquiat then converted the left one into a commemorative coin honoring jazz great Charlie Parker, adding the year of his death on the coin. Parker was a frequent subject of Basquiat’s solo paintings, and bringing him into “Arm and Hammer II” took the work in a deeper direction—converting Warhol’s coolly commercial start-point into a tribute to Black genius, while raising issues of race, music-industry exploitation and the burdens of celebrity.

Collaboration was part of New York’s downtown ’80s art scene, with artists exchanging ideas, motifs and works and arranging exhibitions at the Mudd Club and other nightspots. But, said Basquiat curator and scholar Dieter Buchhart, “nobody did it to this extent and this intensity,” adding that Basquiat and Warhol produced “a very diverse body of work. It’s a big, crazy explosion.” To Haring, the collaborations were “a physical conversation happening in paint instead of words. The sense of humor, the snide remarks, the profound realizations, the simple chit-chat all happened with paint and brushes.” Each of them, Haring said, “inspired the other to out-do the next.”

By late 1985, Basquiat and Warhol had been working together for roughly two years while continuing to create their own art. Their collaborative style had matured, and their contributions became harder to tease apart. “I think those paintings we’re doing together are better when you can’t tell who did which parts,” Warhol mused.

In autumn of 1985, the two unveiled 16 of the works in a downtown gallery show. Tongue-in-cheek publicity photos had them dressed as sparring boxers.

The show bombed. A scathing New York Times review dismissed the collaboration as “one of Warhol’s manipulations,” noting that “Basquiat, meanwhile, comes across as the all too willing accessory” and an “art world mascot.” Warhol took it in stride, but the critique hit Basquiat hard. The collaboration ended. Their friendship endured, at a lesser intensity, as Basquiat’s career continued its rise.

In February 1987, Warhol died suddenly after a complicated gall bladder operation. Struggling anew with addiction, Basquiat died of an overdose some 18 months later. Since then, both artists’ reputations have continued to climb. Each has been the subject of books, films and major museum shows. And each continues to exert an enduring influence on art and pop culture.

Their collaborative pieces are now hailed as remarkable artworks in their own right—the subject of their own books, exhibitions and auction-house triumphs. Utterly improbable and deeply creative, the spiky, sparky bromance between Jean-Michel Basquiat and Andy Warhol lives on in their art.