Greg Tate’s best paragraphs throb like a party and chatter like a salon; they’re jam-packed with names and references that shouldn’t get along but do. Photograph by Janette Beckman / Getty

Greg Tate published his first book, a collection of essays titled “Flyboy in the Buttermilk,” in 1992. It drew from his work at the Village Voice, where he had initially been hired, in the late eighties, to help the alternative weekly cover black music. As he would wryly note years later, the opportunity was born of the paper’s unusual belief that “Afro-diasporic musics should on occasion be covered by people who weren’t strangers to those communities.” At the Voice, Tate became known for the slangy erudition he brought to bear on a range of topics, not just hip-hop and jazz but also science fiction, literary theory, movies, city politics, and police brutality. His best paragraphs throbbed like a party and chattered like a salon; they were stylishly jam-packed with names and reference points that shouldn’t have got along but did, a trans-everything collision of pop stars, filmmakers, subterranean graffiti artists, Ivory Tower theorists, and Tate’s personal buddies, who often came across as the wisest of the bunch.

By the time I learned about “Flyboy,” it was out of print. A friend lent it to me, and, for the first time in years, I contemplated theft. Most critics can recall the encounters with art that left them so entranced that—motivated by mystery, ecstasy, or something in between—they felt compelled to reckon with the experience through writing. And most critics can also recall the critical essays that convinced them that this form of writing could be as exhilarating as art. When I first read Tate, I had cycled through a few of the more obvious approaches to cultural criticism, from the twisty and gonzo to the arch and obscurantist. But, reading Tate, I was drawn to his sense of otherness; he wrote from a perspective that felt both inside and outside. The possibilities of that perspective struck me when I got to the piece in “Flyboy” about Don DeLillo. Tate admires DeLillo, but, in the essay, he muses playfully on the vast literary terrain available to the alienated white male writer.

For a generation of critics, Tate’s career has served as a reminder that diversity isn’t just about a splash of color in the group photo; it’s about the different ways that people see, feel, and move within the world. These differences can be imperceptible, depending on where your eye lingers as you scan the newsroom. What made Tate’s criticism special was his ability to theorize outward from his encounters with genius and his brushes with banality—to telescope between moments of artistic inspiration and the giant structures within which those moments were produced. “Flyboy 2,” published earlier this month by Duke University Press, largely consists, like its predecessor, of critical essays, interviews, profiles, and short riffs. But, a quarter of a century on, the question animating his work has come into sharper focus. What he’s been exploring through his criticism has been something “less quantifiable,” as he puts it, than culture, identity, or consciousness. What Tate wants to understand is “the way Black people ‘think,’ mentally, emotionally, physically,” and “how those ways of thinking and being inform our artistic choices.”

In “Flyboy 2,” Tate’s excursions into this territory are more collaborative than they were in his earlier criticism. This becomes most explicit in a conversation with the late composer and bandleader Butch Morris, famous for “conducting” large, improvised jazz ensembles. The two discuss collective creativity, and Tate wonders aloud, “Are we talking chaos or democracy here?” The question resonates with his own approach to writing. He’s always allowed himself to come across as wide-eyed, mystified, and curious during his interviews; in so doing, he has elicited unusually insightful commentary from his interlocutors. A 1990 conversation with Ice Cube, who was then at the height of his powers, lays bare hip-hop’s theatricality, its blockbuster instinct for performance and play. (When Tate asks what responsibility Cube has to his audience, the rapper says, “My only responsibility is making funky records.” But Tate presses him, calling him out for his contradictions and trying to convince him of his power.) A mid-nineties interview with the trumpeter Wynton Marsalis turns on the tension between jazz’s old-school interest in virtuosity and the coarser rebellion of the hip-hop generation. “When this fad is gone, it’s gonna be back to the blues,” Marsalis says, “always has been and always will be.” But Tate, again, pushes back, pointing out the “tone and texture” of rap, the “soulful properties” that guide sampling. Eventually, Marsalis budges, ever so slightly.

Both of these pieces, among the oldest in the collection, help to establish jazz and hip-hop as part of the same continuum of expression—and they help ground Tate’s contention that black art is a centuries-long strategy for “erasing the erasure.” Drawing such connections across time and space is crucial for Tate. In successive paragraphs on the artist Kara Walker, Tate compares her to Art Spiegelman and then to Michael Jordan. The grace and mutant flexibility of the dancer Storyboard P calls to his mind the minimalist composer Terry Riley. Elsewhere, Tate draws on conversations with a friend to trace an improbable musical lineage. “My buddy Craig Street and I used to joke that the only people we knew who liked Joni Mitchell were Black people,” he writes, before positing that her style anticipated hip-hop. In another essay, about the painter Kehinde Wiley, famed for rendering young black and brown men in the hyper-naturalistic style of heroic portraiture, Tate writes:

Black masculinity is already context. Already a fiction and an ethnographic narrative. Already the shortest distance between two points and the hypotenuse of a square. Already a moonshot, a roll of the dice, the luck of the draw, the pick of the litter. Last hired, first fired, only standing president to be called out by his name like so; ‘uppity tar baby.’ Rich nigra, poor nigra, White House-ensconced nigra still just a nigra.

Tate’s perspective feels especially vital when he writes about an artist like Wiley, who inherited hip-hop’s disdain for masters and then turned it into something else. In contrast, Tate’s own relationship to hip-hop has become more distant, as the music and the business around it have become inextricable. People should hate Eminem, Tate writes in a 2004 essay, not because he’s white but “because he gets paid by the industry to be whimsical and personal”—a freedom that is rarely extended to rappers who aren’t white. Tate constantly maintains an awareness of the ways that even the most intimate and ephemeral creations can be monetized: a particular attitude, a way of standing. Tate has a keen sense for the way that both artists and communities discern where they fit in the world, and what is expected of them, and then either go along for the ride or carefully plot their escapes. This is why his obituaries for Amiri Baraka, Richard Pryor, and Michael Jackson, all collected in “Flyboy 2,” radiate such an acute sympathy.

The pieces in the new book cluster around the early aughts, and then there’s a bit of a gap until the twenty-tens. This in-between period was when I first met Tate. He had agreed to talk to me about a piece I was writing on the Black Rock Coalition, an organization he co-founded in the eighties. Every now and then, I would see him around Manhattan or Brooklyn. He was making music—he had started a free-jazz big band inspired by Sun Ra and Parliament-Funkadelic called Burnt Sugar. He played a little guitar, but his main job was conducting all the loose energies onstage, the way Butch Morris used to do. I remember going to a few shows just after 9/11 and finding comfort in this weird, futuristic, improvised America. At these performances, there were singers, horns, a cello, and more guitars than seemed strictly necessary. I remember turntables and drums, too, and Vijay Iyer, a future MacArthur genius, on piano. Was it chaos or democracy? At the center of the stage, dressed in a white suit, there was the critic, making art with his hands.