Painted at the very moment when Jean-Michel Basquiat’s ground-breaking practice came to the attention of the international art world, his early cityscape New York, New York (1981) narrates the artist’s dramatic transition from spray painting the streets of Manhattan to painting on canvas.

Unconstrained by convention, his paintings on canvas and found objects of 1980-81 fully embraced the urban environment that surrounded him and speak the language of New York’s city streets. One of the artist’s very best works from this period, New York, New York expertly captures the gritty atmosphere of the city Basquiat grew up in, encapsulating a metropolis in economic dire-straits that bore forth an extraordinarily creative artistic scene at the end of the 1970s.

New York, New York was made for Basquiat’s debut solo exhibition, which took place at Galleria d’Arte Emilio Mazzoli in Modena, Italy in 1981. Never before seen outside Italy, the painting being offered for sale on 26 June is from the same private Italian collector who acquired it in Modena over 35 years ago. Alex Branczik, Head of Contemporary Art for Sotheby’s Europe said: “New York, New York is Basquiat’s early masterpiece, demonstrating the full strength of the artistic conviction that propelled him from street artist to exhibiting studio-based painter. Highly charged and raw with energy, the painting crystallises the brilliance of an enormously talented young spirit on the verge of stardom.”

Basquiat’s inaugural show came about following the artist’s participation in the legendary New York / New Wave exhibition at P.S.1. in 1980 – an underground show at a rundown former school in Long Island that came to define a moment and was recently celebrated in the Barbican Centre's Boom for Real exhibition. It was at P.S. 1 that visionary gallerist Emilio Mazzoli first encountered Basquiat’s work and subsequently set the wheels in motion for the artist’s international debut. The Italian show was named SAMO, after Basquiat’s street tag (an abbreviation for the phrase ‘same old shit’). The exhibition’s title marked the coming of age of the downtown graffiti-poet.

After finally arriving in Modena, Basquiat spent his time in Mazzoli’s gallery making more pictures ready for the opening night of the exhibition on 23rd May 1981. Although very much aligned to the symbolic and raw expressive style of the paintings created in Modena, because New York New York is signed New York 1981, it is likely that this painting was in fact one of the works that Basquiat brought with him on the plane to be exhibited in the Mazzoli show.

Graffiti encompassed a whole range of associations and meanings for Basquiat, from an urban vehicle for free speech to art forms produced by outcasts and native peoples. Though having made the transition from street to studio, Basquiat nonetheless brought the street with him: where his graffiti operated as high art, Basquiat’s high art captured the urban space of the city.

Painted in white on the right hand side of New York New York is the depiction of a skelly court – a children’s street game. The collaged element on which the skelly court has been painted evokes peeling subway posters and commercials, while the criss-crossing of spray painted lines and architectural passages of white and black paint conveys a tumult of forms that imply the vertiginous skyscrapers of New York’s famous skyline. Across a divergent landscape of marks, signs and symbols, Basquiat conveyed the world in which he lived, and crucially, how he made sense of it.

Significantly, New York, New York is one of the first of Basquiat’s works in which the soon-to-be iconic three-pointed crown plays a central role. Basquiat’s shorthand for a long overdue ennoblement of black subjectivity in western art, the crown is repeated twice in this work, emblazoned in metallic-silver spray paint and flanking the left and right sides of the composition.