This year, CNN published a three-part investigation into some claims shrouding the deaths of James Brown in 2006 and his third wife, Adrienne Brown, 10 years earlier. The report details the horrifying conduct—rape, abuse, suspected murder—that shaped the Godfather of Soul’s private life, especially in its second half. Some of the information was already public, including accounts of domestic violence, and the article leaves a number of questions open, such as whether Brown himself was a victim, murdered by one of his hangers-on. Still, now, if not before, listening to the tight funk of tracks like “I Feel Good” inspires more discomfort than awe—a feeling that the song is so tight only because his band feared what their violent boss might do if they ever missed a beat.

The English critic Ian Penman had a similar moment in 2012 while reading R.J. Smith’s Brown biography, The One. Perturbed by Brown’s offenses, Penman suggests that readers may want to “put the book down and go play the music again to remind yourself why you’re bothering. If you haven’t been put off the music for good, that is.” There are countless influential artists, past and present, who have exhibited neither abusive behavior nor objectionable politics. (Brown supported Richard Nixon and lambasted social services, believing that black people should work hard for success, like he did.) If those artists’ music is a click away, why continue listening to Brown at all? Penman, for his part, reminds us that the Godfather’s best music is visionary, cathartic, not to mention ubiquitous. So, can we square art and life? “How,” Penman wonders, “does what is permissible—wild abandon, exaggerated claims, world-encircling desire—find a roost in the grey maze of real life?”

The Brown essay is one of eight collected in It Gets Me Home, This Curving Track, Penman’s second book, after 1998’s Vital Signs. Except for the first chapter, which considers mod culture’s shifting legacy through its ’60s origins and subsequent revivals, each essay focuses on an American male musical icon whose songs are part of our cultural lexicon but whose actions were problematic to varying degrees. Penman respects his subjects—Brown, Charlie Parker, Frank Sinatra, Elvis Presley, John Fahey, Donald Fagen, Prince—but makes sure to attend to “the multi-hued complexity of the artist in question.” Rather than write the linear narratives of so many rock star biopics, he seeks to unravel “a certain taut dialectic between a messy and even desperate private life and the artist’s almost supernaturally elegant, economical song.” (He offers the term “tellyology” to describe other music writing: “shaping history with both eyes on a potential TV series.”)

Whereas some may want a dialectic’s thesis and antithesis to produce a synthesis, Penman finds his chosen figures resisting the equation. They remain split, open: These are men for whom good and bad, among other opposites, weren’t exact polarities. “For Brown, play was always work, but work was never play,” Penman writes. Importantly, “you get a consonant feeling from the music: even at its most avowedly merciful or pleading, his songs carry an almost dementedly wilful, near-threatening charge.” Suffused with personal and historical angst, the effects of racism or classism, and fame, drugs, and masculine hubris, the artists’ lives and work are positioned as separate but reciprocal. Penman, then, seeks out a “roost,” a “home,” from which to gauge the flow of reciprocity and to hear, from a distance, how these bad—but beloved and oft brilliant—men sound now.

Born in 1959, Penman began writing for New Musical Express as a teenager in 1977, where he was part of a crop of young music critics who rejected the conservatism of not just British life and letters but ’70s rock criticism as well. Under editor Neil Spencer, Penman and  colleagues such as Julie Burchill and Paul Morley shaped NME into a Labour-supporting, often irreverent rebuke of the old guard. For Penman in particular, this meant covering a diverse slate of music—reggae, R&B, jazz, pop—in lieu of the punk rock that his peers championed. Punk had “promised all of this change,” he lamented to journalist Pat Long, “but soon we were just going back to the same old rock ’n’ roll thing,” regressive in both politics and style.

Even more than for his taste, Penman became known for vibrant, erudite prose that drew heavily on critical theory. It’s common in his early pieces on artists like Kid Creole to find quotations from Barthes, Derrida, and Adorno—thinkers who were popular among ’70s English intellectuals. But Penman’s rarefied references alienated the NME faithful, who “didn’t know who Roland Barthes was and…didn’t care,” as journalist Paolo Hewitt suggests. Even some with literary bents, like the Camus-enamored Cure, voiced frustration. In 1979 the band performed a song called “Desperate Journalist,” with the lyrics “Ian Penman / He uses long words / Like ‘semiotics’ and ‘semolina.’” To the Cure, his diction seemed merely pretentious: “Rude soulless obliqueness.”

But to others, his work broke ground. Continental concepts could illuminate the constructs behind music, and evocative songs could help to recontextualize arcane theory. Penman left NME in the mid-’80s and began contributing to publications such as The Independent, Sight & Sound, and The Wire. He refined an expansive style of critique less in line with consumption-minded music writers like Robert Christgau than with clever polymaths like critic and novelist Gary Indiana—one of 10 writers to blurb It Gets Me Home—and the social art historian T.J. Clark, whose latest collection, Heaven on Earth, likewise reassesses canonical (visual) artists. By the ’90s, Penman had become a forerunner for a generation of music journalists like Simon Reynolds, Kodwo Eshun, and Mark Fisher, who instrumentalized academic credentials to untie the knotty social implications of popular music.

Written from 2012 to 2019, the essays in It Gets Me Home originated in the London Review of Books and, questionably, the conservative-think-thank-affiliated City Journal. Framed as long-form, historiographical reviews of one or more (auto)biographies, the essays cite more music historians than French theorists: Penman says he aimed for an “entirely accessible” prose, arriving at one laced with the energy of a longtime fan, detached enough to read against the grain. Despite limited references to continental philosophy, It Gets Me Home still betrays a foundation in psychoanalytic theory and semiotics. Presley and Sinatra can’t escape their mothers; Fahey and Prince tried to mute the “author function,” blurring personal details and subverting audience desires (and, later, producing mediocre music, Penman says). Throughout, Penman strips the sheen from pop sounds and images to expose interpretable signs.

But these artists rarely signified clearly. As insiders who felt like outsiders, they tried on masks—race, ethnicity, gender, sound—in desperate attempts to find comfort in their position. If Penman is less critical of such identity plays (Presley’s absorption of black and white music) or constructions of otherness (Sinatra’s Italian identity), his attention to each era’s musical and social values renders the men resistant to tweet-size takes. After writing the Prince essay—the final and longest chapter, on the artist’s ’80s heyday and subsequent missteps—Penman admits that he felt “not an inch nearer” to understanding his subject. Prince was always someone else, after all: toying with his voice and point of view, rechristening himself as a symbol. “As if there was the man and there was some kind of rigorously controlled image,” Penman concludes in his introduction, “and in-between… nothing.” Appearing to recognize the limits of foundational postwar criticism, Penman poses a challenge: Can we see man, image, “nothing” in one frame? What do we learn if we do?

The 1988 Charlie Parker biopic Bird opens with F. Scott Fitzgerald’s famous quote, “There are no second acts in American lives.” Parker, who died at 34, never had a chance at a second act; it could be said that Penman’s other artists didn’t really, either, for after a decade of peerless creative production, each fell deeply into himself. Often with the help of bad managers or prescription-happy doctors, they became trapped in a dystopian version of their careers’ first acts. “Brown’s story surely illustrates the dark side of the American Dream,” Penman writes. “Paranoid, reclusive, self-cancelling.” The dream proved to be a liminal space, like purgatory; in some ways their judgment falls to us—critics, listeners, privy to a canon of popular songs and the details of a publicized private life. How can we shape the artists’ second acts?

Should we? Written in 2012, Penman’s phrase “self-cancelling” doesn’t connote what it does today, but readers in 2019 may hear “cancel culture” in the distance. For men who slept with teenagers, abused partners or hung out with murderers, no amount of drug use or the dubious moral laxity of previous decades excuses their actions. Sometimes Penman appears too lax himself, too focused on semiotic play. In the Fagen essay, he eulogizes the artist’s outmoded form of hip: the trickster type who never says what he means. And while Penman appreciates the new, he’s wary of losing the sounds and energies of bygone eras. “Whole swaths of culture are in danger of being reforgotten, belittled, or neutered in divisive ‘culture wars,’” he writes, originally in City Journal, “(with errors of taste and scale on both sides).” Yet today are the stakes are such that we can’t really say what we don’t mean? The middle ground, between both sides, that many (white) punk-era radicals like Penman seek appears as a necessary casualty. This doesn’t herald the destruction of great art but rather the constant renegotiation of its cultural position.

Fortunately, a more generative approach to both sides emerges in It Gets Me Home. In the Sinatra piece, Penman examines the crooner’s late-’60s struggle with irrelevance. Perhaps against his will, Sinatra recorded happening new songs like “Downtown” and Joni Mitchell’s “Both Sides, Now.” While Penman dubs them “flops,” the covers are instructive. In “Downtown” he hears an index of the singer’s misery, a “strange back-of-the-throat gurgle—eurrrgh—like something sour brought up by that morning’s hangover heave.” Sinatra recorded the dark, underappreciated 1970 album Watertown, which Penman finds “reflective and fatalistic…disarmingly convincing.” Watertown’s power points not just to the impossibility of charting Sinatra’s career as a downward slant but also to the nondeterministic exchanges between life and work. For Sinatra, despair forged both good art and bad, reflection and recklessness. It’s with these asymmetries—both sides—that his later music ought to be heard.

Mitchell is among a few musicians who appear throughout It Gets Me Home. (Billie Holiday is another; it would’ve been fruitful for Penman to reckon closer with the gender dynamics of popular reception and permissible behavior.) If Sinatra looked to Mitchell for what was happening, she helped Prince to recalibrate. In the ’90s and ’00s, remnants of what motivated the young Prince to flout musical, racial, and sexual convention had curdled, and the artist’s inert new songs offered the only whiff of who he had become. But late in life Prince changed his tune. He “[played] all the old songs again: just himself, a piano and a microphone.… Maybe revisiting the emotions buried in those songs might have helped jog loose something inside.” Penman is reminded of Mitchell’s 2000 album Both Sides Now, which features standards and an updated version of the title track, one of her early hits. She “sings [the songs] inside out,” he writes, “sings them with her 57-year-old voice and all it contains: all the love, desire, and disappointment.”

This, ultimately, is what we listen for, at least in music that matters to us—for the specificity of the moment of creation and the developments that surround it. Music doesn’t signify as words do; it’s rarely an effective conduit for truth or political discourse, as Penman argues via Fahey and Adorno. At the same time, music resists linguistic misdirection, the effects of saying what one doesn’t mean. “Shelves of books are devoted to unearthing the fugitive ‘meaning’ of pretty song lyrics,” Penman writes, “yet often it’s some forgotten scrap of melody that cracks us apart.” If he likes for artists to resist straightforwardness, it’s because it opens the door for the production of new meaning, the recoding of their words according to how they are said. For instance, disappointed in Presley biographies, Penman turns to a late-period compilation, on which “we finally get to hear both sides of Elvis: good twin, bad twin; the creepy and threatening Elvis as well as the more familiar croony sentimentalist.” It’s through an affective listening experience that the threads of Penman’s unraveled dialectic—biography, history, sound—appear to come back together.

But there’s an additional thread now: the listener. In an essay on Proust that provides one of Penman’s epigraphs, Walter Benjamin wonders if an artist’s life and work always manifest “the undisturbed unfolding of the most fleeting, most sentimental, weakest hour in the life of the one to whom they pertain.” Benjamin reads Proust’s asthma in the rhythms of his syntax: certainly a less damning fault than megalomania, et al. But more important, Benjamin saw the artist’s time of vulnerability as a point at which readers might weave their own being into the work. “When Proust in a well-known passage described the hour that was most his own,” Benjamin says, reading between the lines, “he did it in such a way that everyone can find it in his own existence.” Our existence thus woven with the artist’s, we’re enabled, if need be, to start the process of unraveling for good.