In early December at Art Basel Miami Beach, rappers seemed to outnumber artists at times. Andre 3000 presented an exhibition of the 47 sloganized jumpsuits he wore on the Outkast Reunion Tour. P Diddy was on the lookout for his very own Picasso, 2 Chainz turned up to party with designer Jon Buscemi and producer Swizz Beatz curated an exhibition for international art group SCOPE. Meanwhile A$AP Ferg, Danny Brown and OG Maco were pulling in large crowds from the graffiti-filled streets of the Wynwood neighborhood.

“Thirty years ago,” the artist Hank Willis Thomas said, “those would have been the signifiers that maybe you shouldn’t be there.”

But that juxtaposition of the seemingly gauche and apparently high-brow wasn’t that odd during a year in which artists tried to rethink where hip-hop belonged, and seemed to conclude that as well as having a presence in the charts, it still could command cultural clout in the hotspots of the high-art world. In November at San Francisco’s Yerba Buena Center for the Arts, Marc Bamuthi Joseph presented Clas/Sick Hip-Hop: 1993 Edition, an event which filled the venue with two stages of emcees, musicians, composers and dancers. Kahlil Joseph, a compelling, innovative film director, debuted his 14-minute film collaboration with Kendrick Lamar, m.A.A.d, at a Sundance event in Los Angeles (the film will begin a run at LA’s Museum of Contemporary Art in March). RZA reverse-engineered rap product into art object, offering to auction a Wu-Tang Clan double album, Once Upon a Time in Shaolin, as a one-of-a-kind piece. The special museum exhibition tour he promised where visitors would come to listen to the album through gallery headphones hasn’t yet materialised, but the single original copy sits in a silver-and-nickel-plated box outside of Marrakech, Morocco, ahead of its auction online.

Shabazz Palaces - Dawn in Luxor (directed by Kahlil Joseph)

All of these followed art-school dropout Kanye West’s 2010 collaboration with neo-expressionist painter George Condo on My Beautiful Dark Twisted Fantasy and custom Birkin bags. Jay Z and Mark Romanek produced a video for his song, Picasso Baby, by staging a 2013 performance at the Pace Gallery that drew a who’s-who of the art (and hip-hop) world for a re-appropriation of conceptual artist Marina Abramovic’s The Artist Is Present at New York’s MoMA.

But things weren’t always so amicable between the worlds of hip-hop and art. When hip-hop was nascent, the art world loved it before hating it. The relationship was summed up in an awkward scene from Charlie Ahearn’s 1982 film, Wild Style, when downtown gallerist Niva Kislac invites hip-hop artists including Fab 5 Freddy (who attended the Picasso Baby event) and graffiti writer Lee Quiñones to her apartment for a late-night party. Niva has collected Warhol, Stella, Lichtenstein, and now she wants the real street stuff. Lee is both disgusted and titillated.

For hip-hop artists and graffiti writers, the scene was based on reality. As a young painter from Brooklyn, Fab 5 Freddy (real name Fred Brathwaite) was enamoured with pop art and graffiti. He wanted to break open doors closed to young artists of color and make their culture legible to the art world. “I was trying to put a frame around the whole thing,” he recalls. “I was aspiring to paint, to be in media, to work in film.”

In 1979, Freddy got himself and Quiñones an exhibition of their canvas pieces with Claudio Bruni’s Galleria La Medusa in Rome. In 1980, he announced his aesthetic intentions by painting his famous Campbell’s Soup full-car subway train, making Warhol hip-hop as much as he was making himself pop. In 1982, Wild Style helped introduce hip-hop globally.

By then, Freddy had bridged New York City’s hip-hop and art worlds, bringing in outsiders like Afrika Bambaataa, Futura and Jean-Michel Basquiat, who injected new energy into the cloistered downtown art scene. What happened is what always happens when culture is desegregated from the bottom up: creativity exploded and everyone won. The feverishly miscegenating scene produced Afrika Bambaataa and the Soulsonic Force’s Planet Rock and Blondie’s Rapture. It made stars out of Freddy’s close friend Basquiat and a bleach-blonde who called herself Madonna.

After Basquiat’s death, that initial cross-pollination subsided as art and hip-hop went their separate ways. But in the work of artists like Gary Simmons and Renee Green and curators like Thelma Golden, its aesthetics still seeped indelibly into contemporary art, all but unremarked and unrecognized by the art world.

In 2001, at the Bronx Museum of the Arts, Lydia Yee and Franklin Sirmans curated a defining show, One Planet Under a Groove: Hip-Hop and Contemporary Art, which featured the work of Simmons, Green, Basquiat and Keith Haring, and forced a reconsideration of older artists like David Hammons, Martin Wong and Adrian Piper. The show also introduced new artists like Sanford Biggers, Nadine Robinson and Juan Capistran.

Jean-Michel Basquiat: hip-hop’s original art interloper. Photograph: Lizzie Himmel/AP

But these artists were rarely understood by the art establishment, which saw them working against hip-hop aesthetics rather than embracing it. They were called “post-Black” or “post-identity” artists, and positioned outside of their own spheres of influence.

Then Jay Z discovered Basquiat.

Freddy recalls a party where the excited rapper said he had just been given a private tour of a new Basquiat exhibition about to open at Brooklyn Museum. He wanted Freddy to tell him everything about the young artist, whose biography seemed to parallel his own. That was the point at which many say the cultural traffic between the hip-hop and art worlds began to reverse.

“Basquiat is sort of a heroic entry point [for Jay Z]. He was born in the same borough. He even made real hip-hop music,” says Franklin Sirmans, one of the curators of the expansive 2005 exhibition that served as Jay Z’s introduction. The rapper began dropping Basquiat references into his songs, and in 2013, he paid $4.5m for Basquiat’s 1982 painting Mecca.

In a 2012 Instagram post, Rick Ross pulled Lyor Cohen to pose with him in front of an award-winning Richard Mosse photograph. Ross wrote, “Just purchased my 1st piece from Art Basel w/my lil homie Lyor. #bossup”. Sirmans says that, after their work with Kanye and Jay Z, George Condo and Marina Abramovic “emerged with more celebrity and more renown than their long careers had ever seen. Jay and Kanye put them over the plateau.”

But Sirmans offers another view. In these elite spectacles, he says, “hip-hop is subsumed, buried in the smoke of global popular culture”. Instead, as the critic Antwaun Sargent has noted, the real influence hip-hop is having on contemporary art can be seen in the work of cutting-edge artists like Rashaad Newsome, Jordan Casteel, Awol Erizku and the fashion designer Shayne Oliver. If in the past black artists were forced to confront issues of invisibility, this new wave of artists use painting, dance, performance, fashion and object-making to ask questions about the visibility that hip-hop confers on young African Americans now.

Hank Willis Thomas’s Raise Up. Photograph: Goodman Gallery press@goodman-gallery.com

And if there remains any doubt about whether hip-hop still has the capacity to shock and inspire, look at what Hank Willis Thomas did amid the Art Basel bacchanal. He unveiled a sculpture called Raise Up, depicting 10 black men with their arms high in the air. Adapted from an apartheid-era photo by Ernest Cole, Willis Thomas’s work features South African gold mineworkers subjected to a humiliating end-of-day, full-body strip-search to ensure they had not stolen any precious metals. After the non-indictment of Darren Wilson just days before, the sculpture accrued new layers of meaning. Raise Up echoed protests across the country that transformed Michael Brown’s and the mineworkers’ gesture of submission into a symbol of mass resistance.

As for Fab 5 Freddy, he has come back to his painting practice recently and has had occasion to look back. Five years ago, he attended a screening of Wild Style on the lawn at the Hollywood Forever Cemetery, the final resting place for Cecil B DeMille, Rudolf Valentino and Jayne Mansfield.

When the scene of him and Lee at Niva’s apartment party came up, he had a moment. Turning from the screen, he saw he was again standing next to an art-world insider – this time Jeffrey Deitch, then the head of the Museum of Contemporary Art in Los Angeles, who was standing, cheek by jowl, on a cemetery lawn full of people who had grown up on hip-hop. “Damn,” he thought to himself, “I guess we were on the right track 30 years ago.”