Unlike most rock stars, painters and sculptors tend to live outside the public eye, spend much of the day alone, and get better as they get older. But Jean-Michel Basquiat (1960-1988), a graffitist turned painter who ascended to fame and acclaim as young man, was a “vision of cool,” according to Gagosian Gallery, who “spurred the Neo-Expressionist art boom” of the 1980s before dying of a drug overdose at 27. With his premature passing, this handsome “denizen of the explosive and decadent New York underground scene” joined the likes of Jim Morrison, Janis Joplin, Jimi Hendrix, Kurt Cobain and Amy Winehouse as a member of the infamous ‘27 Club,’ a morbid term for a list of mostly rock stars who died at age 27, often due to drug or alcohol abuse.

Basquiat has not faded away since his death. The Brooklyn-born painter of Haitian descent has had artwork in numerous gallery exhibitions, been the subject of two museum retrospectives and been memorialized in the films Basquiat, a 1996 biopic directed by Julian Schnabel, and The Radiant Child, a fawning 2010 documentary. Mythologized as a “street poet” and hard-living bohemian, it can be difficult to distinguish the merits of Basquiat’s artwork from his legendary status. An exhibition at Gagosian Gallery in Chelsea, now in its final weeks, surveys the artist’s oeuvre, filling the massive gallery with over fifty works and offering visitors a fresh opportunity to assess the artist’s legacy.

The uneven Gagosian show reveals a precocious talent whose bohemian lifestyle gave rise to some powerful images of urban energy and, just as frequently, empty angst. It is the earliest works here that have vitality. In many of the later paintings Basquiat’s creative process looks rushed, perhaps due to the demands of a hungry marketplace. The best pieces in this show do not easily reveal their making, images with gritty urban elegance, while the weakest works are overrun with filler, a seemingly random assortment of the artists trademark symbols and politically charged catchphrases that appears to strain to cover the canvas before petering out.

Untitled (L.A. Painting), 1982, a highlight of the exhibition, is over seventeen feet long. The work has the scale and look of a city wall with an urban patina, as though the canvas has been covered in posters and paint, scarred by the city’s millions of residents, defaced by vandals and then those defacements themselves defaced until a convincing snapshot of a city in motion, in all its rough, gritty splendor, is expressed. Behind the organic look of Untitled (L.A. Painting) is a sophisticated hand that has created sensitive transitions between colors and combined a range of materials (house paint, spray paint, paper collage, crayon) into a cohesive composition.

But paintings from only a few years later seem tired. In Deaf, 1984, a work that appears to have been painted with a fork, a roughly outlined figure plays a half-drawn harp. The musician is placed in a sea of alizarin crimson and, in what seems like a strain for meaning by Basquiat, he scrawled the words ‘BLIND HARP PLAYER’ above the figure. As the artist’s celebrity grew, his urban “primitivism” becomes increasingly forced. Frogman, another work from 1984, seems little more than decorative.

An international art star at 21, Basquiat’s paintings were driven by a lifestyle that proved unsustainable. Though Gagosian Gallery’s exhibit celebrates the painter’s “spontaneity, savagery and wit, urbanity and primitivism,” the show also illustrates the upside of unhurried artistic development.

Jean-Michel Basquiat, on view through April 6, 2013, Gagosian Gallery, 555 West 24th Street, New York, NY, 212-741-1111, www.gagosian.com

More information about Xico Greenwald’s work can be found at xicogreenwald.com