Upon first glance, one could assume that Hilton Als, the theater critic and writer for the New Yorker, is a man. That he is African American. Digging a little further by reading his essays and articles, one could expand that to describe him as an African American man with a brilliant eye for art and criticism. Going yet further, one might add a taste for the dramatic. With his new collection of essays, White Girls, Als examines the experiences he has lived within and across these identity markers, but he also pushes much further: by expounding on figures such as Flannery O’Connor, Andre Leon Talley, Richard Pryor and Truman Capote, he fully inhabits their sensibilities and demons. Hilton Als, the African American man with a brilliant eye for art and criticism and a taste for the dramatic, becomes, in many stunning ways, a white girl and everything that phrase can mean.

Als’ approach succeeds largely because of the intellectual curiosity and empathy that exists throughout his writing. In his essay “Philosopher or Dog,” which rips at America’s understanding of Malcolm X, he mentions that the words “otherness and difference,” define our era but he also summarizes those same words as “beside the point” and then says “never mind.” Freeing himself of this sense of otherness, then, is key to the essays.

“One of the things we fail to do is empathize. We pity more than we empathize,” Als says. “There is a human quality to empathy. That involves imagination, and that’s not something that is encouraged enough.”

This imagination enables Als to analyze culture and history—both personal and beyond—with great poignancy and depth. Throughout the work, he is both Hilton Als and the man whom Hilton loves; he is Flannery O’Connor and the South itself. And, most especially in the opening essay “Tristes Tropiques,” he is both a black man and a white woman standing at the same cocktail party in 1980s New York, having two completely different experiences.

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And what to make of that simultaneously mythical and very real white girl? What to do with that title that hovers over a highly sensitive study of culture, identity, race and love?

“I think that she is many things,” Als says. For the reader, there are implications of privilege, perhaps beauty, and sometimes of a closed awareness. Als explains that the phrase itself came to him from his experience working in fashion.

“The workers backstage would refer to the black models as ‘black girls,’ and I never heard anyone say ‘white girls,’ ” he explains.      

The work delivers an ever-present attention to these daily provocations of race. In the essay “The Only One,” Als spends pages crafting the legendary icon of Andre Leon Talley: a visionary steeped in Baudelaire, a global colossus of fashion and wit, an enigma of race and physicality and language confounding his industry. And yet, the essay ends brutally with Talley seemingly at the peak of his career and influence, hosting a luncheon in Paris at the start of the couture season, surrounded by “white girls” and serving as their queen—until one of the attendees delivers an unexpected insult that leaves the reader frozen and speechless.

There is no escape, in Als’ world, from the eye of the mythical white girl, and from the ideal she represents. Every heartrending figure in his essays, from the young Truman Capote sexualizing himself for the dust jacket photo that made him infamous, to the genius Richard Pryor settinals coverg himself on fire, is an example of the deepest yearning to be this “white girl.” Of the Capote photo, he writes: “It is an image that is an assertion, a point, asserting this: I am a woman.”

By the end of the collection, what is most impressive about the work is not that Als has succeeded at cultural criticism, but that he has so powerfully and thoroughly written about himself via these cultural touchstones. This shouldn’t come as a shock, considering his intellect and upbringing.

“I was always looking for metaphors to describe myself and other people,” he said of his youth. “I went to a Rauschenberg retrospective at the age of 15, and I didn’t understand it. Then I followed the docent around…and the top of my head came off.”

While there is a recurring sense of nostalgia in Als work—for another New York, for a more robust cultural dialogue, a lover and best friend who has gone quiet—he maintains an active passion for the present. “I’m all for newer voices," he says. “Voices that are struggling to be heard.” He is also hopeful that there will be better material that “details the lives of real black people.”

“[In art], we have a long way to go in terms of success being a part of black lives,” he said. “That will change because of examples like Michelle Obama—even more than her husband, I think.”

Ultimately, though, there is heartbreak at the end of a work like White Girls. Beyond cultural criticism, the book also contains elements of fiction and sections that seem to verge on memoir. The painful alienation between best friends and lovers described in “Tristes Tropiques” also feels like a separation that the narrator experiences from himself.

“I didn’t know that I was writing a book about loss,” Als says as he recalls the Ginsberg line, “I have seen the best minds of my generation destroyed by madness.”

And thinking of what happens to an individual when his friends, or his family, who are ultimately his audience, pass on, Als says: “There are worlds of self-creation being lost when the people who you do it for die.”

David Garza lives in New York City.