Last week, Sean “Diddy” Combs made headlines with his history-making purchase of a painting by renowned artist Kerry James Marshall during a Sotherby’s Contemporary Art Evening Auction in New York, setting the mogul back $21.1 million. In addition to being the latest indication of Diddy’s wealth, the painting, titled “Past Times,” is historically significant due to it being the most expensive piece by a living black artist to be sold to a buyer, scoring yet another groundbreaking moment for Diddy and the black community as a whole.

The purchase is also the latest instance in which the worlds of hip-hop and high-end art have crossed paths, a relationship that runs deeper than one may think.

During hip-hop’s earliest incarnations, graffiti artists throughout New York City’s five boroughs decorated the city’s subway system and architecture with their groundbreaking brand of street art, which would influence and inform the work of an array of artists that would become icons within the art community. One of the first figures to help bring hip-hop and graffiti to the art gallery was Fab 5 Freddy, a streetwise graffiti writer with style, charm and gift of gab unique of its own. A member of the Brooklyn-based graffiti crew the Fabulous 5, in 1979, Fab 5 Freddy showcased his talents overseas in an exhibition in Rome, Italy, which can be credited as the genesis of hip-hop’s transition into the world of fine art on an international level. Immersing himself in the punk-rock and art scenes brewing in downtown Manhattan during the late 70s and early 80s, Fab 5 Freddy would become a major conduit and ambassador for both sides, hobnobbing and curating events with transcendent figures like Jean-Michel Basquiat and Keith Haring while spreading the hip-hop gospel.

Speaking of Basquiat and Haring, both were key figures in capturing the aesthetic and sentiments of hip-hop and the sociopolitical issues plaguing the black and Latino communities and conveying it through their work, resulting in some of the more captivating and pivotal images of the decade, from Basquiat’s 1983 piece “Untitled (History of the Black People),” to Haring’s “Crack Is Wack” mural in Harlem. Unfortunately, both artists would pass away during the height of their careers, adding to the allure of their work, which is among the most coveted by art enthusiasts today. While the popularization and commercializing of graffiti may have opened the doors for hip-hop within the art world during the 80s, the culture was still rooted in the streets and frowned upon within certain realms of society, making it hard for rap artists and members of the hip-hop community to stray outside of their comfort zones and truly find common ground with curators and art enthusiasts at the highest rungs of the industry.

However, the explosion of rap music and urban culture in the 90s would translate into big business, birthing a new generation of moguls and millionaires with aspirations that stretched beyond their humble beginning and experiences.

Producer Swizz Beatz was among this crop of young creatives and businessmen looking to become young black entrepreneurs and expand their portfolio, but unlike many of his contemporaries, who delved into the alcoholic beverage or fashion business, the Bronx native set his sights on becoming an art collector after being introduced to Peter Max’s work during a boat cruise in 1999. While Swizz was admittedly green to the game during his first years collecting art, he credits industry veteran David Rogath with setting him on the right path and showing him the ropes. “He was the first person paying attention to me in a gallery because I was in there every week,” Swizz recalled in an interview with W Magazine. “And he gave me some advice. He said, ‘Listen, don’t try to paint the big picture in one day. Find one piece, then another piece.’”

In the wake of that meeting, Swizz has since picked up where Fab 5 Freddy left off, slowly bridging the gap between the art world and hip-hop during the better part of the past two decades through a multitude of ventures and partnerships, whether it be deejaying events at Art Basel, joining the board of the Brooklyn Museum, or launching his No Commission Art Fair. Recently, Swizz announced plans to give $5,000 away to 20 different artists to put on their own art show, during which they will be able to sell their work directly to the buyer while keeping 100% of the proceeds. Swizz and his wife, R&B singer Alicia Keys—who own pieces from a list of renowned artists that include Kaws, Maya Hayuk, Jean-Michel Basquiat, Andy Warhol, Ernie Barnes and Keith Haring as part of their Dean Collection—are at the forefront of hip-hop’s infiltration of the art world. A number of other artists have also followed Swizz’s lead, most notably JAY-Z, whom Swizz gifted with sculptures of a car hood sculpture and a diamond dust alligator that he created himself.

The ultimate trendsetter and curator of cool, JAY-Z’s style has grown from decadent to refined as the hustler-turned-mogul’s interests have grown in taste, marked by his growing interest in the world of fine art, which began to rear its head during the roll-out for his Magna Carta Holy Grail album. From name-dropping artists like Rothko, Basquiat, Warhol, Picasso, and Koons to filming the “Picasso Baby” music video at the Pace Gallery in New York City as part of a six-hour performance art piece, Hov’s art game is not to be trifled with, as works from the aforementioned Warhol, Basquiat and Picasso, as well as Tim Noble, Sue Simmons, Ed Ruscha, David Hammons, Damien Hirst, Richard Prince, Paul Pfeiffer, and Laurie Simmons help comprise his collection of pieces. Other veterans and style icons who have helped make art become trendy in hip-hop are Pharrell Williams, who interviews artists as part of his “ARTST TALKS” YouTube series, and Kanye West, who helped merge the two worlds through everything from his album covers to making Basquiat a hot commodity to millenials and elder statesmen alike.

However, with all of the strides that hip-hop has made in the art world, Diddy’s record-setting purchase of “Past Times” is the most impressive thus far and is not only a sign of black excellence on the part of Kerry James Marshall, but of hip-hop’s continued growth and maturation as it continues to evolve and impact all facets of society on a global level.

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