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Attention: Team Acme
We’re thrilled to announce a new company-wide initiative. This week, we’ll be rolling out a robust suite of new A.I. tools, designed to future-proof our workflows and insure that we remain best in class when it comes to employing the very biggest tools in the white-collar workforce.

As part of this rollout, you can expect enhanced collaboration with a range of newly A.I.-optimized losers and douche bags. Some of these tools may feel familiar, but please note that they have undergone a meaningful transformation in the past six months, and are now fully agentic when it comes to annoying you.

Please begin working with these tools immediately. At the end of the quarter, we’ll be circling back to assess key performance indicators.

James
Works in marketing. Last year, he was a crypto tool, making frequent references to the “on-chain community.” After a brief pivot to brewing mushroom coffee in the office kitchen as part of his “cognitive stack,” he has reëmerged as the company’s Chief A.I. Growth Architect, a role that appears to consist mostly of coming up with novel ways to spam people.

Tara
Known for her capable client-facing presence, Tara has begun leveraging generative A.I. to scale her personal brand as a “female founder.” A recent LinkedIn post opens with a vulnerable story about her pet iguana’s heat-lamp preferences and concludes with the revelation that “the real moat isn’t efficiency. It’s warmth.”

Matthias
Seemed normal, until a breakup caused him to spend an entire long weekend lurking on Moltbook. Was reborn as an “A.I. Doomer.” Begins Slack messages with “In eighteen months, none of this will matter.” Has replaced his profile photo with a picture of a crumbling statue.

Preston
Now talks openly about his poetry degree from Bard instead of saying he “went to college on the East Coast.” Has started wearing scarves and spending company time writing sonnets, which—in two years, when we’re unshackled from capitalism—he knows will be Earth’s primary currency.

Bryan
Relentless self-explorer who has started feeding transcripts of his interactions with every woman in the office to his A.I. agent, and tasked it with forming a strategy for getting him laid. So far he’s had zero sex but generated substantial training data. His agent notes a particular brick wall when it comes to macking on Emily.

Emily
Previously the office social secretary, Emily has quietly declared it a feminist move to outsource all emotional labor to L.L.M.s. Her Slack messages wishing you a happy birthday and offering condolences after the death of your dog are suspiciously bullet-pointed. ♦

In Hollywood, and at the Oscars, “hope” is a very big word. Chloé Zhao used it in her recorded introduction to a clip from her film “Hamnet,” and Conan O’Brien, hosting the festivities, offered it as a reason to hold that big party in troubled times. He exhorted the crowd to enjoy the night “in the spirit of optimism.” But the most hopeful moment of this year’s ceremony came at the very end, when the final award, for Best Picture, was bestowed upon “One Battle After Another.” Its writer and director, Paul Thomas Anderson, a film-history fanatic who’d already just collected two awards (for Best Director and for Best Adapted Screenplay), offered a history lesson, citing the five nominees for Best Picture who were in the running fifty years ago, at the 1976 ceremony: “Jaws,” “Barry Lyndon,” “Nashville,” “Dog Day Afternoon,” and “One Flew Over the Cuckoo’s Nest” (which won). Here’s the good news: the best four of this year’s ten nominees in the category—“Sinners,” “The Secret Agent,” “Marty Supreme,” and, yes, “One Battle After Another”—are better movies than those five putative classics. (I’m sure that Anderson didn’t mean it that way, but, to quote Hamnet’s dad, “What’s done is done.”)

What makes these new films better is their wilder, freer, more original and personal approach to cinematic form, in addition to their candor about history—their directors’ manifest self-consciousness regarding their own, and their films’, place in the world, and in the art of movies itself. As Lynette Howell Taylor, the president of the Academy, said in her speech, the organization that voted on these awards comprises more than eleven thousand members, from around the world, and, at least to some extent, the results suggest greater openness and curiosity than earlier generations of Oscars might have shown. “One Battle After Another” was the night’s big winner, with awards in six categories (Picture, Director, Supporting Actor, Adapted Screenplay, Editing, and the first ever for Casting), ahead of “Sinners,” with four (Actor, Cinematography, Original Screenplay, and Score), and the tone of O’Brien’s opening monologue, oscillating between zingers and earnest gravity, suggests why.

“One Battle After Another,” with its opening scene involving a military-run concentration camp for rounded-up immigrants, its colossal second half centered on organized resistance to help immigrants avoid government raids, and its vision of a cabal of white (and Christian) supremacists holding secret sway in Washington, was practically torn from the headlines in advance. Its vision of indignation and resistance lurked behind every one of O’Brien’s thinly veiled jokes about Donald Trump (whose name was never mentioned) and his reference to “chaotic, frightening times,” and behind Jimmy Kimmel’s gag on the muzzled media of “North Korea and CBS,” and echoed the acceptance speech of David Borenstein, a co-director of “Mr. Nobody Against Putin” (which won Best Documentary Feature), who explained, correctly, that his film shows the authoritarian outcome of compromise, complicity, and government co-option of media. “One Battle After Another” is a movie of notable artistry, indeed one of the year’s best, but its triumph is less aesthetic than political.

The consolidation of media looms over the year’s awards in an innate way, too: both “One Battle After Another” and “Sinners” (directed by Ryan Coogler) were produced by Warner Bros. The movie-division heads who had the foresight to greenlight two such audacious projects, Pamela Abdy and Michael De Luca, were both hired by David Zaslav, soon after he became Warner’s C.E.O., when the studio merged with Discovery. Now, of course, Warner Bros. Discovery has accepted a takeover offer by David Ellison, who has already acquired Paramount—and, with it, CBS—with the result that the network’s news division has been placed in Bari Weiss’s hands, and Paramount’s slate of releases has been severely thinned out. If the deal is concluded, it’s hard to imagine Warner Bros. backing such artistically bold and politically candid movies.

“Sinners,” set in rural Mississippi in 1932, is a story of Black twin brothers (both played by Michael B. Jordan, who won the Oscar for Best Actor) who, flush with money they stole from gangsters, open a juke joint and find themselves menaced by the Ku Klux Klan and by an altogether unexpected enemy: white folk-music vampires. The film’s meticulous detailing of life under Jim Crow and its allegorical vision of the cultural predation and erasure facing Black art and culture are no less relevant to current events than the action in “One Battle After Another,” but the kinds of stories it tells aren’t those of the headlines. This isn’t Coogler’s fault, needless to say, but that of the people who decide the headlines. (Andrew Jarecki and Charlotte Kaufman’s nominated documentary feature “The Alabama Solution,” about Jim Crow-like oppressions prevalent in prisons today, stands in a similar relation to the Best Documentary Feature winner, “Mr. Nobody Against Putin”.)

Although Anderson won for direction—and I’d contend that the scene that put it in the bag for him is the bravura chase near the end, which is dramatically arbitrary but old-school exciting in a way that few action films manage to be—the triumph of Coogler’s directing found acknowledgment in the award for Jordan’s twin performances. Directing and acting are inextricably connected; all the nominated performers are skillful and charismatic, but the distinction of their performances also conveys the tone that the directors set and the substance and range that the scripts offer. In “Sinners,” Coogler does more than tweak genre; he tweaks genre acting, though there’s exuberant energy and hectic comedy, gravity prevails throughout, and Jordan, tapping into it, turns the dual roles into ones that, for all their expansive power, are anchored by a fundamental, nearly sacramental quiet. It’s a performance that invites viewers to lean in and listen closely—exactly the opposite of what Anderson gets from Leonardo DiCaprio and Sean Penn in “One Battle After Another.” In that movie, blusteringly goofy roles yielded performances that were monotonous and hollow. Penn won for Supporting Actor nonetheless, and it’s noteworthy that he defeated Benicio del Toro, from the same movie, whose performance—altogether finer, subtler, and more imaginative—is far less showy. This was a classic case of the award going for the most acting rather than the best acting.

A similar misconception prevailed in the award for Best Editing, and the mistake was heralded by the preamble of its presenters, the father-and-son pair Bill and Lewis Pullman, which expressed the view that good editing should be “invisible.” If the winner, “One Battle After Another,” doesn’t quite meet that classical ideal, it doesn’t brazenly reject it, either—in stark contrast to the editing in “Marty Supreme,” which is by far the most original of the year. And, although “Marty Supreme” is arguably a case of the most editing, it’s also something of a manifesto on editing itself, a work of kaleidoscopic fragmentation that seems to belong to an entirely different artistic generation than Anderson’s. The editing of “Marty Supreme” was done by Josh Safdie, the film’s director, and his co-writer, Ronald Bronstein, two independent-film luminaries who brought a shattered-glass sensibility to the finished product. (“Marty Supreme” was, startlingly, not even nominated for Original Score; I found the electronic score, by Daniel Lopatin, to be both overbearing and unforgettable, far more distinctive than most of the nominees.) The film’s outsider style remains out of bounds even when crafted inside the borders of Hollywood.

The generational gap on display in the hall—and even more evident outside of it, in living rooms—was reflected in the side business of comic sketches about the movie industry. One burlesqued the Oscar broadcast’s impending move to YouTube, in 2029. Another, about translating the show into youth lingo (ending with “six-seven”), elicited a seemingly spontaneous addendum from O’Brien, to the effect that no young person watches network television, anyway. There was a skit about a company engaged in “preserving film history . . . for the smart-phone generation” by hacking movies’ horizontal rectangles into vertical slices: thus the title of “The Godfather Part II becomes “odfat II.” And O’Brien and Sterling K. Brown did a routine impersonating Humphrey Bogart and Dooley Wilson in “Casablanca,” to show how that film might have been, had it followed Netflix’s “second-screen” guideline, about repeating previously dispensed narrative information, on the assumption that viewers are distracted by another screen.

Clearly, Hollywood is running scared from streaming, short-form videos, and the perception of generational obsolescence. O’Brien did a riff about Amazon being shut out of this year’s Oscars, capped with the quip, “Why isn’t the website I order toilet paper from winning more Oscars?” First, history: in 1966, Paramount became part of the Gulf and Western conglomerate, which produced industrial chemicals, ran parking lots, and owned funeral homes; for much of the nineteen-eighties, Columbia Pictures (now called Sony) was owned by Coca-Cola. Nothing wrong with a laugh, but, in 2025, Amazon released one of the year’s best movies, “Hedda,” which should have been nominated in a bunch of categories, including Best Picture, Direction (Nia DaCosta), Lead Actress (Tessa Thompson), Supporting Actress (Nina Hoss), Adapted Screenplay (DaCosta’s script is based on Ibsen’s play “Hedda Gabler”), and Cinematography (Sean Bobbitt). I suspect that the film’s provenance did indeed count against it with Academy members, but the result is deeply unfortunate for the art of movies.

With these tensions and anxieties in the foreground, the ceremony was oddly divided against itself. The tone of its plentiful political humor, more wry than confrontational, suggests yet another element of fear, issuing from the heavy hand of Donald Trump on the future of studios; the Department of Justice’s antitrust division is expected to approve David Ellison’s takeover of Warner Bros. Discovery. With the movie business facing political, economic, technological, sociological, and generational pressures, this year’s ceremony had something of a funereal air. Much of the comedy went far beyond jibes into gallows humor, concluding with a parody of the ending of “One Battle After Another” in which O’Brien, offered the job of the Oscars’ Host for Life by the fascistic Christmas Adventurers, ends up murdered and cremated.

That sense of doom may be why the memorial segment, so often of a pro-forma show of melancholy, felt unusually raw, even continuous with the whole: Billy Crystal spoke of his friends Rob and Michele Reiner, Rachel McAdams eulogized Diane Keaton, and, above all, Barbra Streisand commemorated Robert Redford. She recalled working with him on “The Way We Were” and concluded by singing that movie’s title song, with a fervor that seemed to surge forth with the pent-up power of a lifetime.

Between Streisand’s gloriously nostalgic performance and Anderson’s fond reminders of the 1976 Oscars, the idea that Hollywood’s best days are in the rearview mirror emerged as the official line of the ceremony. On the other hand, for all the mournful reserve of the stage business, the movies that were most celebrated exhibited neither political timidity nor artistic caution. The real point of the Oscars is the movies, and the question isn’t whether great ones will continue to be made but whether that will still happen in Hollywood. ♦

Not enough witches have won Oscars. True, Ruth Gordon did win Best Supporting Actress for “Rosemary’s Baby” (1968), in which she was a cunning satanist next door, dishing up chocolate mousse from Hell. But that’s just a drop in the cauldron. Where were the awards (or, indeed, the nominations) for Margaret Hamilton in “The Wizard of Oz” (1939), Helen Mirren in “Excalibur” (1981), Anjelica Huston in “The Witches” (1990), Tilda Swinton in “The Chronicles of Narnia: The Lion, the Witch, and the Wardrobe” (2005), Kathryn Hunter in “The Tragedy of Macbeth” (2021), or even Angela Lansbury in “Bedknobs and Broomsticks” (1971)? The nominations Cynthia Erivo and Ariana Grande received for their performances in “Wicked” (2024) perhaps went some way toward redressing this grievous wrong, though they conspicuously failed to repeat that trick this year for the ill-received—and ill-conceived—sequel, “Wicked: For Good.”

Yet, happily, there was recognition for sorcery on Sunday night, when the ninety-eighth Academy Awards were handed out. To no one’s surprise, Jessie Buckley was crowned Best Actress for “Hamnet,” in which she plays an Elizabethan woman who has the primordial magic of the forest running through her veins. Among the Best Supporting Actress contenders, Wunmi Mosaku stood out, in “Sinners,” for her role as a skilled hoodoo healer who is alert to the threat of a vampire siege. Mosaku, a Nigerian-British actor of stealthy gravity, lost out to a showier, witchier performance: Amy Madigan won for the supernatural horror picture “Weapons,” in which she gives a properly Gordon-esque turn, funny and frightening in equal measure, as Aunt Gladys, a psychotic hag with an impressive bag of tricks: using a snappable twig and droplets of her own blood, Gladys invades the minds and bodies of unsuspecting suburbanites and forces them to do her sinister bidding. Oscar voters proved powerless to resist Madigan’s spell; we should have guessed the outcome from the ceremony’s opening clip reel, in which Conan O’Brien, the evening’s host, turned up in Aunt Gladys’ clown wig and makeup. What is it that Dorothy says at the end of “The Wizard of Oz”? Ah, yes: there’s no face like crone’s.

Madigan, who is seventy-five, previously received an Oscar nomination for the 1985 drama “Twice in a Lifetime,” a title that now seems prophetic. Since then, she’s figured prominently into some fairly memorable Oscar moments. When Marcia Gay Harden pulled off a startling Best Supporting Actress win for her role in Ed Harris’s film “Pollock” (2000), there was Madigan in the front row, clapping with violent elation. (Harris and Madigan have been married since 1983; the two sat together and sweetly embraced on Sunday night, when Madigan’s name was called.) And, at the 1999 ceremony, Madigan and Harris sat in silent, stone-faced protest when an honorary Oscar was awarded to the director Elia Kazan, who, in 1952, avoided the Hollywood blacklist by naming eight colleagues as former Communist Party members before the House Un-American Activities Committee. It was a scene that triggered flashbacks to Madigan’s performance in “Field of Dreams” (1989), as an outspoken liberal who, at a school P.T.A. meeting, righteously opposes a “Nazi cow” responsible for a book-banning campaign.

The ninety-eighth Oscars ceremony was a P.T.A. meeting of a different kind, the P.T.A. in question being the director, screenwriter, and producer Paul Thomas Anderson. His film “One Battle After Another” dominated the evening with six wins, the first of which came in the Academy’s newly inaugurated Best Achievement in Casting. Cassandra Kulukundis, the film’s casting director, gushed about her decades-long collaboration with Anderson—and then marvelled at the fact that she had somehow managed to win an Oscar before he had. “I hope you get one tonight!” she added, to much laughter from the crowd. Kulukundis needn’t have worried. Anderson won in all three of the categories for which he was nominated: Best Directing, Best Adapted Screenplay (the film is loosely based on the Thomas Pynchon novel “Vineland”), and Best Picture, which he shared with his producers, Sara Murphy and the late Adam Somner. The wins ended a career-long Oscars drought that, before this year, had seen Anderson go zero for eleven across six earlier films—several of which, including “Boogie Nights” (1997), “There Will Be Blood” (2007), and “Phantom Thread” (2017), have made him the most revered American auteur of his generation.

Onstage at the end of the night, Anderson recalled that the Best Picture nominees for the film year 1975 were “Dog Day Afternoon,” “One Flew Over the Cuckoo’s Nest,” “Jaws,” “Nashville,” and “Barry Lyndon.” “There is no best among them,” he said. “There is just what the mood might be that day.” Respectful disagreement aside—the best of the five is clearly “Barry Lyndon”—it was a gracious acknowledgment of the other nine Best Picture nominees, and especially of “Sinners,” a critical and commercial smash that had been nipping at the heels of “One Battle After Another” all season long, though not, perhaps, as closely as its most passionate partisans had hoped. But “Sinners,” which had already earned a record-breaking sixteen Oscar nominations, made history nonetheless: its director of photography, Autumn Durald Arkapaw, became the first woman ever to win the Oscar for Best Cinematography—a ludicrously overdue precedent that Arkapaw acknowledged by asking every woman in the theatre to stand. “Sinners” claimed four Oscars in total, including Best Original Score, for the composer Ludwig Göransson; Best Original Screenplay, for the writer and director Ryan Coogler; and Best Actor, for Michael B. Jordan, who starred as gunslinging identical twins. The only other actor to have managed this feat was Lee Marvin, who won Best Actor for dual roles in “Cat Ballou” (1965).

Should we be annoyed, dismayed, worried, jaded, or relieved that, at the second Oscars of the second Trump Administration, barely a month into a spuriously waged war on Iran, so many of the winners’ speeches steered clear of politics? Was it incumbent upon the artists behind “One Battle After Another” and “Sinners,” two Oscar front-runners of genuine political heft, to speak out as forcefully against white supremacy as their films do? This reserve has become the Academy’s way: it’s not as if the “Oppenheimer” juggernaut of two years ago initiated a flood of speeches denouncing nuclear proliferation. The Oscars are clearly not the Grammys, where this year’s big winner, Bad Bunny, called out ICE in one of his speeches. Nor are the Oscars the Berlin International Film Festival, which became mired in controversy last month, as journalists flooded press conferences with questions about Palestine and Israel, Trump and ICE, and the role of politics in cinema.

Anderson, who has consciously avoided politics in the multiple speeches he’s given this season, did lower his guard a bit when he won the Best Original Screenplay Oscar: “I wrote this movie for my kids,” he said, “to say sorry for the housekeeping mess that we left in this world we’re handing off to them.” Anderson was not alone in invoking children and the future; the Danish-Norwegian filmmaker Joachim Trier, accepting the award for Best International Feature Film for the drama “Sentimental Value,” paraphrased an idea from James Baldwin’s essay “The Children Are Ours”: “All adults are responsible for all children,” Trier said, “and let’s not vote for politicians who don’t take this seriously into account.”

These were stirring, unimpeachable sentiments; imagine the furor that might have erupted, by contrast, if Sean Penn, who famously disdains awards ceremonies, had shown up to collect his prize for Best Supporting Actor, for “One Battle After Another.” When he won Best Actor in 2004, for “Mystic River,” he kicked off his speech with a jab about the nonexistence of weapons of mass destruction in Iraq. You suspect that he might have had a thing or two to say about the real-life applications of his “One Battle” character, a white-supremacist Army colonel who oversees an ICE-like crackdown on immigrants.

Even so, the night was not an entirely apolitical affair. Javier Bardem, presenting Best International Feature Film with Priyanka Chopra Jonas, started his remarks with a forceful “No to war, and free Palestine.” O’Brien threw in a jab about the failure to hold pedophiles accountable in the wake of the Jeffrey Epstein files. Predictably, the most topically urgent speeches could be found in the nonfiction-film categories. Gloria Cazares spoke movingly about her daughter, a victim of the 2022 school shooting in Uvalde, Texas, as she accepted the award for Best Documentary Short with Joshua Seftel and Conall Jones, the filmmakers of “All the Empty Rooms,” which takes viewers into the bedrooms of children lost to gun violence across America. David Borenstein accepted the Best Documentary Feature Oscar for “Mr. Nobody Against Putin,” which he described as a film “about how you lose your country.” Clearly not speaking only about Vladimir Putin’s Russia, he added, “You lose it through countless small little acts of complicity.”

Jimmy Kimmel, who presented both nonfiction awards, mocked “Melania,” Brett Ratner’s widely panned documentary about Melania Trump, and slammed the ascent of Bari Weiss in David Ellison’s media empire, Paramount Skydance. “As you know, there are some countries whose leaders don’t support free speech,” Kimmel said. “I’m not at liberty to say which. Let’s just leave it at North Korea and CBS.” It was a sharp dig, though I do wish that Kimmel, in invoking authoritarian regimes, had thought to mention Iran—or that someone in the writer’s room had thought to shout out the Iranian director Jafar Panahi, perhaps the greatest and certainly the bravest of this year’s nominated filmmakers. Panahi’s film “It Was Just an Accident,” a nominee for Best International Feature and Best Original Screenplay, is partly drawn from his own experiences as a prisoner in the Islamic Republic. Like the superb Brazilian film “The Secret Agent,” from the director and screenwriter Kleber Mendonça Filho, Panahi’s film is a political thriller of searing moral urgency. The fact that neither film won anything is a reminder of the Academy’s cultural myopia: for all its efforts to diversify and internationalize its voting membership, the organization seems largely oblivious to the finest, most vital work being done by filmmakers outside of America.

Ultimately, it wasn’t the brutalities of the Trump Administration or Israel’s atrocities in Gaza that drew the most sustained protest on Sunday night but rather the encroaching threat of irrelevance for a film industry facing challenges on many fronts: declining ticket sales, the rise of A.I., soul-crushing corporate mergers. In one bit after another, O’Brien celebrated the cinema of the past, with nods to “North by Northwest” (1959) and “Casablanca” (1942), in order to lampoon where Hollywood seems to be heading. Among his targets were the appalling distortion of films to fit smartphone screens and the tendency of scripts in the Netflix era to become nonstop-exposition machines. He playfully posited a worst-case scenario for 2029, when the Oscars, a longtime fixture of broadcast television, will begin streaming exclusively on YouTube. The segments were funny, even when the laughter caught in your throat. Long before an uncommonly graceful and gimmick-free In Memoriam segment, with extended individual tributes to Rob Reiner, Catherine O’Hara, Diane Keaton, and Robert Redford, there was no mistaking the faintly elegiac cloud that hung over this year’s Oscars—the sense of a ceremony, and of an entire industry, unable to stop memorializing itself. The greatness of this year’s finest films aside, it will surely take more than fresh reserves of movie magic, let alone a snap of Aunt Gladys’s twig, for a spirit of optimism to prevail again. ♦

There’s a scene in “Pretty Woman” in which Julia Roberts, as Vivian, a sex worker hired by a “corporate raider” played by Richard Gere, attends a polo match dressed in a demure polka-dot sundress and a boater hat. She almost blends in—until a player makes an impressive shot and she starts pumping her fist, chanting, “Woof! Woof! Woof!” Moviegoers in 1990 would have clocked the reference: Vivian was tuned in to “The Arsenio Hall Show.” Its host, the eponymous Black comedian, would make his entrance as a rowdy section of his audience called the “dog pound” barked on cue.

“The Arsenio Hall Show” premièred on January 3, 1989, and in the course of the next six seasons became the epicenter of early-nineties cool; even the logo had color blocking. Hall wore flashy suits and streetwear and eschewed the traditional host’s desk in order to sit closer to his guests, even if it meant risking a contact high from a seemingly stoned Tupac Shakur. The show had the energy, and the soundtrack, of a night club. With musical guests such as A Tribe Called Quest and Salt-N-Pepa, it was the unofficial late-night home of hip-hop. When Fred Rogers, of “Mister Rogers’ Neighborhood,” came on, Hall gifted him a colorful leather jacket to match his own and exclaimed, “This gives new meaning to boys in the hood!”

The biggest names of the nineties stopped by to earn street cred: Tom Cruise appeared to promote “Interview with the Vampire”—and to dap Hall. In 1992, the Presidential hopeful Bill Clinton joined the show’s band to play “Heartbreak Hotel” on the saxophone; afterward, he joked with Hall about having smoked pot, claiming that he really did try to inhale.

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Hall’s interview style was loose and bawdy, part of a countercultural posture—embodied by musicians like Prince and Madonna (of assless pants and cone-bra infamy, respectively)—that rejected the sexual puritanism sparked by the AIDS crisis. In 1991, the singer Sinéad O’Connor appeared on Hall’s show after boycotting the Grammys, citing the music industry’s “false and destructive materialistic values.” Referring to news reports that a British d.j. had suggested that O’Connor needed a spanking, Hall jokingly offered his services. “What are you doing later?” she replied with a smirk.

When Hall took on the topic of race, he did so in a newly proud, confrontational register. In the early nineties, Black culture was adopting the anti-assimilation tenor of Spike Lee movies and of albums like Public Enemy’s “Fear of a Black Planet.” African Americans weren’t trying to move on up so much as force mainstream America to prove that it could be down. Robert Matthew Van Winkle, better known as Vanilla Ice, also appeared on Hall’s show in 1991. His début single, “Ice Ice Baby,” had become the first hip-hop song to hit No. 1 on the Billboard charts. Hall asked Van Winkle about rumors that his “street” persona was a ruse. “I am from the streets,” Van Winkle pushed back, “and if you can’t see that I’m from the streets then you’re blind, because the majority of white people, you know, cannot dance.” Van Winkle had brought Flavor Flav along, prompting Hall to ask, “Is that to show that you have a Black supporter?”

“The Arsenio Hall Show,” in its first week on the air, came in second in the ratings, after Johnny Carson’s “Tonight Show”—but Hall trounced Carson in the highly coveted under-thirty-five demographic. Two years later, “Saturday Night Live” aired a sketch in which a desperate late-night host named Carsenio (Dana Carvey) dons an oversized red suit and adopts Hall’s risqué, race-conscious style of humor in an attempt to appear hip. “Have you ever noticed how white guys hold themselves down there?” he says, reaching for his groin. “What are they holding down there, anyway?”

In “Arsenio” (Simon & Schuster), a forthcoming memoir written by Hall with Alan Eisenstock, a co-author of “Hang Time: My Life in Basketball,” by Elgin Baylor, and other celebrity memoirs, the late-night host describes that “S.N.L.” moment as surreal. Growing up in Ohio, Hall had dreamed of being Carson: “When most kids in Cleveland wanted to be football stars like Jim Brown, I wanted to be an old white man with a talk show.” Six decades later, the job of telling corny jokes to a studio audience of Midwestern tourists still belongs largely to white men—one of the many reasons that Hall’s book, though essentially a chronicle of early-nineties cultural politics and his place within it, feels well timed.

Late night these days has lost its after-hours edge, with publicist-friendly interview questions and political “satire” that reads like something off a teleprompter at the D.N.C. Today’s late-night hosts have faced censorship nonetheless. Jimmy Kimmel’s show was briefly placed on hiatus after he called out the right wing’s rush to judgment about the motives of Charlie Kirk’s alleged killer, and “The Late Show with Stephen Colbert,” on CBS, was cancelled three days after Colbert criticized the network’s decision to settle a lawsuit with Donald Trump. But these examples are more symptoms of the Administration’s thin skin than signs of actual bite. (George Cheeks, the chair of TV media at Paramount, has said that the decision to cancel Colbert was a financial one.)

Late night’s self-muting hasn’t gone unnoticed. In March, Vanity Fair ran a story on “The New Late Night.” What struck me, besides the fact that none of the ten featured hosts occupies a late spot—they’re YouTubers and podcasters—was how many of them have made forbidden speech their brand. The comedian Ziwe Fumudoh got her start with the web series “Baited with Ziwe,” which brought on “cancelled” celebrities in a kind of public-shaming ritual; the comic Kareem Rahma, of “Subway Takes,” invites his guests to offer contentious opinions while riding public transit. (Rahma told my colleague Andrew Marantz that Kamala Harris’s team wouldn’t let her express her actual take—that people shouldn’t remove their shoes on planes—for fear of offending barefoot-leaning voters.) Oddly missing from the article was Adam Friedland, the edgelord comedian who recently hosted Gavin Newsom on his show. The California Governor had just told CNN that the Democrats should focus less on “pronouns” and be more “culturally normal.” Friedland advised Newsom that the next time the right complained about a Black Little Mermaid, his party should instead double down: “Say, ‘Pardon me. You’re a pussy, and that’s a baby movie.’ ” Newsom chuckled nervously. In an era in which politicians are focus-grouped to the point of parody, the exchange felt like samizdat smuggled across the borders of liberal piety.

Late night isn’t just a time slot. It’s a concept, a temporal metaphor for what we can get away with under the cloak of night, when the kids are asleep, when we can claim innocence—nothing else was on! Like the “late-night” dissidents of YouTube, Hall rose to popularity by talking up the verboten. In his day, when the term “inner city” circulated as a racist bogeyman, Hall brought the soundscape of “the hood” into people’s living rooms. When promiscuity had been branded a public-health crisis by the religious right, he asked Madonna about the stamina of her boyfriend and “Dick Tracy” co-star, Warren Beatty. “Joan Collins once called him sexually insatiable,” Hall offered. Madonna begged to differ: “I would say that he’s satiable.”

In 1988, the year before his show premièred, Hall starred in “Coming to America,” a romantic comedy about an African prince (Eddie Murphy) who travels to Queens, New York, along with his aide (Hall), to find a bride. They make a stop at the Jackson Heights Y.M.C.A., where a Miss Black Awareness pageant is taking place. A reverend, also played by Hall, launches into a spirited sermon about the bikini-clad contestants: “Man cannot make it like this! Larry Flynt! Hugh Hefner! They can take the picture, but you can’t make it! Only God above, the Hugh Hefner on high, can make it for ya!”

Hall later told Howard Stern that he’d based the character, in part, on his father, Fred Hall, whom he calls, in his memoir, a “strict, conservative Baptist preacher.” Not so conservative—at sixty-five, he married Annie Martin, the twenty-one-year-old daughter of a church deacon. Hall was born to the odd couple in 1956 in Cleveland. (The “dog pound” is a reference to a raucous fan section in the city’s football stadium.) In his book, Hall describes their union as an opposites-attract situation. Fred listened to Mahalia Jackson spirituals, while Annie preferred Elvis and Ray Charles—what Fred called “hip-slapping music.” Nonetheless, Hall identifies a sensuality in his father’s sermonizing which would inspire his own late-night persona. “He doesn’t just preach,” Hall writes. “He puts on a show. With handkerchief in hand, he prowls the pulpit, he gesticulates, he growls, he shouts, he whispers.”

When Hall was five, his mother moved out, taking him with her. She worked long hours and got him a babysitter—an Emerson TV set, on which he would watch Carson, Merv Griffin, and Dinah Shore. “I get hooked on Dinah!, not what you would expect from a Black kid living in the ghetto,” he observes. Then again, representation was scarce—Jet magazine ran a column called “Television” that listed every Black person who was going to appear that week. But to the young Hall the color line wasn’t the biggest hurdle—bedtime was. He was in grade school, and Carson came on at 11:30 P.M. He writes, “I turn the sound way down, then crawl so close to the TV screen that I feel as if I’m practically inside The Tonight Show set, sitting next to Johnny.” He hosted the first “Arsenio Hall Show” in his basement. His musical guest, “Junior Brown from down the street,” sang the Temptations’ “Get Ready” on a Mattel Show’N Tell.

Fred Hall had hoped that his son would join the clergy, but Hall dreamed of becoming a magician, just like his idol, Johnny Carson. Hall’s book is in some ways a magician’s memoir of making it, capturing a working-class kid who pulls opportunities out of a hat. A teen-age cousin of Hall’s, who came to live with him and his mother after becoming pregnant, brought a book called “Magic for Beginners” home from the library. Hall taught himself tricks, sprinkling jokes into his performance: “I know all the white magicians say abracadabra. I say collard greens.”

Hall is frequently described as the first Black late-night talk-show host, but his memoir corrects the record. That honor belongs to Ellis Haizlip, the host of “Soul!,” which aired on PBS from 1968 to 1973, with guests including Toni Morrison, Al Greene, Muhammad Ali, Stokely Carmichael—and a fifteen-year-old magician named Arsenio Hall. Vertamae Smart-Grosvenor, the celebrated griot active in the Black Arts Movement, had seen Hall performing magic at Karamu House, a historic African American theatre in Cleveland, and passed along his card to a producer at “Soul!” Soon, Hall was on a plane to New York to make his first TV appearance. (Hall would later invite young talent on his show, including a six-year-old Elvis impersonator from Hawaii named Bruno Mars.)

Hall pivoted to comedy when he realized that he was getting bigger cheers for his one-liners than for his card tricks. He began listening to the records of the standup comedian Redd Foxx. Foxx had come out of the Chitlin’ Circuit, a national vaudeville-esque network of venues for Black performers which emerged during Jim Crow. Foxx and his mentor, Moms Mabley, blended folklore, political commentary, and a subversive style of blue humor. Moms Mabley used the erotic to challenge the image of the desexed mammy; Foxx, conversely, played into the stereotype of the oversexed Black male, influencing later comedians such as Richard Pryor and Chris Rock. In 1993, when Hall received the Richard Pryor Award at the Soul Train Comedy Awards, he brought Pryor, then on a mobility scooter, onstage. The pair received a standing ovation, and a woman in the balcony shouted, “I love you, Richard!” Pryor shouted back, “Well, suck my dick then!”

The history of late night is a kind of dialectic between the traditional and the transgressive, the adult in the room and the kid who refuses to be tucked in. For a time, those parts were played by Ed Sullivan, the host of “The Ed Sullivan Show,” and the upstart Steve Allen, a former radio host who, in 1954, created and hosted the “Tonight Show.” In “Inventing Late Night,” a 2005 history of the original “Tonight Show,” the writer Ben Alba muses, “It all seems so simple: the home base desk, the opening monologue, the announcer/sidekick, the horsing around with the bandleader, the breezy celebrity chats, the wacky stunts, the comedy sketches. . . . Five nights a week.” But, he notes, “this formula did not exist before Steve Allen.”

As a radio jockey, Allen had his staff pick up “kooks” off the street whom he’d interview on the air. He brought the same audaciousness to late night. But his approach wasn’t just structurally unconventional. When Sullivan refused to have Ingrid Bergman on because she’d had an affair with the married director Roberto Rossellini, Allen booked her on his new Sunday-night show. He invited on the boundary-pushing political comedian Lenny Bruce and devoted an entire episode to McCarthyism.

Allen eventually ceded his seat to Jack Paar. Then, in 1962, Johnny Carson—acerbic but amiable—took over, transforming the “Tonight Show” into a national landmark. When Carson retired, in 1992, Bob Hope compared it to “a head falling off Mt. Rushmore.” But, after living through the cultural turbulence and the political disappointments of the seventies, baby boomers were eager to topple institutions. Enter David Letterman, a late-night host who often broke the fourth wall to mock the very act of television-making. In an episode from 1986, he joked, “Most Friday afternoons, we tape a piece for our program on the streets of New York City. Now, this, of course, takes planning, meticulous preparation, and a lot of hard work, so it was only a matter of time before we said to hell with it.” He then followed a pair of tourists from Louisville around for the afternoon, nudging them to Trump Tower and, eventually, to the inside of Trump’s office. “We’ll do a couple real-estate deals in Louisville,” the future President offered.

By the early eighties, Hall, who had moved to Los Angeles after graduating from Kent State, was a regular on the standup-comedy circuit, performing at such venues as the Comedy Store and Hollywood Improv and befriending comics including Robin Williams and Eddie Murphy. Hall never got his chance to appear on the “Tonight Show” with his idol behind the desk—Carson’s booker told him he wasn’t a “Johnny guy”—but, in 1983, Letterman had him on. Hall introduced himself: “My name is Arsenio. It’s a very unique name for a Black man. In Greek, it means Leroy.”

Hall once described himself as “the talk-show host for the MTV generation,” and his show did possess, from the start, the kinetic glamour of a music video. In 1988, after Hall had a successful stint guest-hosting Joan Rivers’s short-lived “Late Show,” Paramount offered him his own hour. He made music a centerpiece of the new endeavor, even penning his own theme song, “It’s Hall or Nothing.” His first week, he booked the R. & B. bad boy Bobby Brown for two songs, including a five-minute version of “My Prerogative.” Lucie Salhany, the president of TV at Paramount, objected: “Carson does one song and never more than three minutes.” But when the ratings for the show’s first week, propelled by Brown’s pelvic thrusts, came in, Salhany “practically screams,” Hall writes. Time magazine put Hall on the cover later that year, proclaiming, “We are seeing the future of the TV talk show, and it is, well, funky.”

Forty per cent of the local affiliates that picked up “The Arsenio Hall Show” belonged to a network that had launched a little more than two years earlier—Fox. The new channel soon became home to the largest number of Black-produced shows on a single network in the history of television, including the sketch-comedy show “In Living Color,” sometimes called the Black “S.N.L.,” and the sitcoms “Living Single” and “Martin.” A Nielsen survey from November, 1990, revealed that Black households watched forty-eight per cent more TV than other audiences did. (White audiences, with more disposable income, had begun diverting their eyeballs to cable.) In “Color by Fox: The Fox Network and the Revolution in Black Television,” the scholar Kristal Brent Zook writes that Fox engaged in “ ‘narrowcasting’ or targeting a specific black viewership.” (Zook notes that Pam Veasey, the head writer on “In Living Color,” “cynically referred to it as the ‘Nike and Doritos audience.’ ”)

In the ambitious new book “Black Out Loud: The Revolutionary History of Black Comedy from Vaudeville to ’90s Sitcoms” (HarperCollins), the journalist Geoff Bennett argues that the nineties Nielsen surveys “transformed the career trajectory” of Black comedians. NBC premièred shows like “A Different World,” a “Cosby Show” spinoff set at a fictional H.B.C.U. called Hillman College. Hall spurred this revolution in TV programming by booking its stars, among them Martin Lawrence, of “Martin,” and Lisa Bonet, whose “Cosby Show” character, Denise, attends Hillman. His greenroom became a hangout spot, and an accidental boardroom, for Black Hollywood. “People make connections, pitch shows, propose deals,” Hall writes. “Will Smith and Quincy Jones discuss doing a sitcom about a Black teenager from a poor neighborhood who moves in with a wealthy Beverly Hills family.”

But, as a late-night show designed for a general, cross-racial audience, “The Arsenio Hall Show” also allowed viewers to see how white celebrities, and by extension white people, interacted with Black culture and its makers. The Time profile described “The Arsenio Hall Show” as a “melting pot,” a term that’s as much of a throwback as MC Hammer’s parachute pants. (The rapper first performed “U Can’t Touch This” on Hall’s show.) At a time when mainstream media was warning its audience about “the inner city,” Hall’s show proved that “the street” and its culture—from Reebok high-tops to gangster rap—were objects of white fascination and longing. Hall even made comedic fodder out of the desire for proximity to Black culture. An episode with Mary-Kate and Ashley Olsen opens with Hall teaching the pint-size twins to shoot dice.

Revisiting the culture wars of the late eighties and early nineties, I gathered that the only thing scarier to Middle America than the word “urban” was sex that occurred outside the confines of heterosexual marriage. The AIDS crisis had inspired a wave of conservative backlash against the gains of the women’s and queer-liberation movements. The disease was painted as punishment for a sexually liberated life style. In response, a slew of artists embraced a kind of baroque eroticism. At the 1991 MTV Video Music Awards, which Hall hosted, Prince performed a seven-minute version of “Gett Off” surrounded by dancers simulating an orgy. A year later, Madonna released “Sex,” a coffee-table book that depicted the Material Girl in ménage-à-trois and B.D.S.M. encounters. When Magic Johnson decided to do a sit-down interview about his H.I.V. diagnosis, he chose Hall’s show. Hall suggested that he go on a more serious program, like “Nightline” or “Larry King,” but Johnson replied, “I have to go where I’m comfortable.”

It was in this context that Hall became late night’s most flirtatious host. In 2026, watching a male host encourage a female guest to perch on his lap—as Hall jokingly did with Whitney Houston—might not, shall we say, sit well. (Houston, for her part, plunked down and wrapped her arms around him.) But, back then, Hall’s touchy-feeliness could have had another valence. As he eyed up his ex-girlfriend Emma Samms, an actress on “Dynasty,” when she came on his show, he was flaunting interracial, premarital escapades. One forgets that interracial dating was still considered illicit in the nineties—Spike Lee made the contentious topic the subject of his 1991 film, “Jungle Fever.”

But some thought that Hall wasn’t doing enough boundary-breaking for those most affected by the AIDS crisis. In 1991, activists from Queer Nation interrupted a taping to protest the show’s lack of L.G.B.T.Q. guests. Hall got heated and defensive. “You think I haven’t had somebody on the show because they’re gay?” he yelled. “I’m Black, man. I’m the biggest minority you know about.” In his memoir, he blames the limitations of the era: “What do you expect me to say? Put your hands together for that well-known balladeer and homosexual, Luther Vandross?”

On April 29, 1992, Los Angeles was ablaze. Four policemen who had been captured on video brutally beating an African American man named Rodney King were acquitted of ten of eleven state charges, leading to riots across the city. On the second night of unrest, Hall devoted a show to the verdict. Paramount had safety concerns, but Hall pleaded his case, saying, “Sean Penn already said he’ll come.” (Penn joined Mayor Tom Bradley and the actor Edward James Olmos.) Not long afterward, some music equipment went missing. Hall reported it, and that night a security guard stopped Hall and his assistant as they were driving off the Paramount lot, asking to check the trunk. Hall lost it: “Did you search Ted Danson’s car when he left?” (“Cheers” was shot on the same lot.) Hall’s assistant got out and broke the wooden gate, and the pair drove off. “I’m not proud that we broke the Paramount gate,” Hall writes. “I’m less proud of the anger I feel constantly, coiled inside me like a live electrical wire.”

The atmosphere in Hollywood was shifting. (By 1994, Fox had cancelled its Black sitcoms following Rupert Murdoch’s acquisition of N.F.L. distribution rights.) In Hall’s third year, Salhany had called him into her office—his ratings were dipping. “The show is very . . . Black,” she said, noting that he had referred to a guest as “brother” that week. “Mark Wahlberg,” Hall replied, puzzled. Then, in 1993, CBS announced that the “Late Show with David Letterman” would air in Hall’s usual time slot. Hall knew that Letterman would siphon off younger viewers and told his manager that he was writing a letter of resignation. In February of 1994, Hall interviewed Louis Farrakhan, the notoriously antisemitic and misogynist leader of the Nation of Islam. Farrakhan, who was planning the Million Man March, was set to appear on the cover of Time and was slated to be on “20/20” with Barbara Walters that spring. In April, Hall resigned, but when Paramount announced his departure many had the impression that he had been fired for booking Farrakhan. Hall is adamant in the memoir that he told executives in advance of his plans to leave, therein refuting the idea that he had been the victim of Jewish censorship.

Since the final broadcast of Hall’s show, in 1994, his presence in popular culture has been sporadic. He was the first Black winner of “Celebrity Apprentice,” in 2012, beating out Clay Aiken and raising two hundred and fifty thousand dollars for the Magic Johnson Foundation. In 2013, Hall staged a comeback, relaunching his show on CBS; it was cancelled after one season, owing to poor ratings. Hall recognized that the landscape had changed. He told TV Guide that he didn’t foresee any interviews like the one he’d had with Brooke Shields in 1989, in which he asked her how losing her virginity was going: “We’re in this world now where publicists control this so much, I don’t know if I can have conversations like that.”

There’s an odd dearth of autobiographies by late-night hosts. Carson never wrote one, and neither has Letterman. Fallon and Kimmel have published children’s books. The “Daily Show” host Trevor Noah’s “Born a Crime” focusses on his experiences growing up mixed race in apartheid South Africa. The only real corollary to “Arsenio” is Jay Leno’s “Leading with My Chin,” from 1996. Perhaps Hall, in writing his memoir, sensed that the culture needed a reminder of what “it’s a night thing”—one of his slogans—means.

In the book, Hall writes about a time he took Prince to an “after-hours joint.” “It’s where people go to dance after they finish working. Strippers, pimps, you know, night folks,” Hall explained to the singer. At a makeshift speakeasy in a Los Angeles living room, the legendary musician sat on a barstool, watching intently. He told Hall, “I’m looking at what these girls dance to at three in the morning. What moves them. What makes them put down their drink and dance.” Great late night asks the same questions. Its jokes are for people who stay up late to steal back time for themselves. Being in bed doesn’t mean you’re ready for sleep, and night folks won’t abide hosts who turn their own volume down. ♦

In “Monogamy,” a collection of a hundred and twenty-one aphorisms on coupling and uncoupling, the psychoanalyst and prolific writer Adam Phillips suggests that the faithful and the promiscuous aren’t so different. Both are “idealists,” he writes, “deranged by hope, in awe of reassurance, impressed by their pleasures.” The book criticizes monogamy as “a way of getting the versions of ourselves down to a minimum,” but it doesn’t exactly defend infidelity. Phillips’s real target may be monotony, the offspring of rote rule-following. “We take monogamy for granted,” he writes, and “treat it as the norm,” sleepwalking into a future without considering whether it actually satisfies us. Ironically, Phillips’s strongest defense of sexual exclusivity is that a steadfast union might offer the same turnabouts and dramas, the same incandescences and crashing disappointments, that you’d normally pursue via cheating. “Perhaps we value monogamy because it lets us have it both ways,” he writes—novelty and continuity, enchantment and disillusion, the lives we live and those we merely visit in our dreams.

What do we want from the lives that we secretly imagine for ourselves? “A difficult mixture of the all too familiar and the experimental, the mostly reassuring and the partly disinhibited,” Phillips contends in “The Life You Want” (Farrar, Straus & Giroux), his latest book. When we were children, he continues, our parents recognized some parts of us and not others (athleticism but not musicality, for instance, or cheerfulness but not guile); now we go around both upholding and rebelling against those received regimes. We alternately display and downplay our encouraged aspects, hide and flaunt our uncountenanced ones. “Haunted by the versions of ourselves” that remain unembodied, Phillips writes, we wish to be who we are and also who we aren’t, splitting the difference even in fantasy.

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Admen and bad romance novelists would like us to think that wanting is straightforward—indivisible, intuitive, and perhaps best remedied by credit card. For Phillips, however, wanting isn’t so simple; it has byways and switchbacks, weight and depth. What if we want something forbidden? What if the objects of our longing are socially acceptable but undermine who we’d like to be? What if we try to attain our aims and fail? What if we succeed and are disappointed, or the intensity of our delectation causes us to lose ourselves? And then, Phillips warns, there is the scandalous origin of our wanting: “our helplessness, our abjection . . . and our dependence.” We cannot satisfy ourselves; we must make demands on others; worse, others make demands on us. Interacting with one’s peers “is never exactly what one was hoping for,” Phillips observes wryly in “Missing Out,” a book from 2012 “in praise of the unlived life.” Socializing involves no fewer than “three consecutive frustrations: the frustration of need, the frustration of the fantasized satisfaction not working, and the frustration of satisfaction in the real world being at odds with the wished-for, fantasized satisfaction.” And that, he adds, is when everything goes well.

Yet “it is only in states of frustration that we can begin to imagine—to elaborate, to envision—our desire,” Phillips writes. He’s articulating the traditional Freudian account of fantasy guiding us toward our best-case scenario: the “ordinary unhappiness” of reality, or what Phillips calls “the possibility of a more realistic satisfaction.” But one also feels his work pulling in a less orthodox direction, toward the pleasure of longing itself. For Freud, wishful thinking was an abandonment of reality. For Phillips, it’s an information source, one we jettison too quickly in our quest to be cured. “The Life You Want” finds Phillips chafing at his field’s prescriptiveness and dismayed by our inclination to submit to other people’s preëmptive conclusions about what we want. “Old-fashioned psychoanalysis always had a known destination,” he observes. There’s a risk that the patient gets up from the couch having discovered not her druthers but what Melanie Klein or Jacques Lacan or Sigmund Freud thought her druthers should be. “Describing the life we want,” Phillips cautions, “can sometimes be the most compliant—i.e., defensive—thing we ever do.”

Phillips is a figure for our therapy-soaked era, even if, for him, therapy feeds into and enables life, whereas we often seem to view life as feeding into and enabling therapy. He’s spent decades translating specialized concepts for general audiences—demystifying transference and projection, peeking under the hood of everyday occupations such as tickling and being bored, drawing on classic works of literature to illustrate the relevance of his field to ordinary experience. A shaman of the psychoanalytic Slate pitch, he often adopts an impish persona, issuing counterintuitive pronouncements about the benefits of quitting, pessimism, or shame. He once told The Paris Review that his adolescent study of English literature prepared him “to ironize the ambitions of grand theory.” Elsewhere, he has remarked with an unmistakable air of indulgence on how much of human endeavor—from art and prayer to political activity—is explicable as a form of attention-seeking.

In his published writing, which extends to more than twenty books, Phillips shows a love of mischief and tomfoolery. His wordplay is sporadically self-delighted; his pose of guileless receptivity caused Joan Acocella to compare him, in this magazine, to a child wondering what would happen if he pushed a pencil up his nose. He believes that we are incorrigibly self-defeating, that we constantly obstruct our own knowledge because we fear being in a position to sate our wayward desires. Hence, perhaps, the contrarianism, a commitment to reversing whatever expectation the reader might be imagined to hold, in an attempt to disarm and deprogram, possibly even cure her.

Phillips is a Freudian, but a selective and partial one, preferring to emphasize his predecessor’s sensitive, more literary aspects. The Austrian doctor was interested “in sentences, in the fact that language is evocative as well as informative,” Phillips told an interviewer, after he was tapped to edit a volume of the Penguin Modern Classics edition of Freud. In “Becoming Freud,” a slender, circumlocutory biography, Phillips conjures a “champion” for patients, “someone who, like a good parent, or a good art critic, could appreciate what they were up to.”

He can be flippant about psychoanalysis, in one essay describing the analyst’s interpretation of the analysand as a “sophisticated form of interruption” undertaken to make the analyst feel “important.” In “Irreverence,” an essay from the new book, he depicts the titular concept as a way of testing authority (whether your target can withstand such shot-taking) and also a love test (whether your target will want to remain on reasonably good terms with you). If “the irreverent are wholly dependent on those they mock,” he writes, irreverence is also, potentially, “a sign of growing up.”

By that standard, the most recent work, animated by the question of what therapy should be and how it might help you get the life you want, is pretty mature. With nose-thumbing insouciance, Phillips recruits the pragmatic philosopher Richard Rorty—or an imagined version of him—to vocalize his discontent with the strictures of his discipline. Rorty used the phrase “God terms” for ideas, such as human nature or objective reality, that alienate us from our agency by appealing to a higher truth. Phillips, a Londoner, takes him as a stand-in for American optimism about the power of positive thinking. “The Life You Want” sets out to shape Freud into a more amenable ancestor, someone better suited to Phillips’s purposes. It’s what Rorty would call a creative “redescription” of the goals of psychoanalysis, redescription being the quintessential pragmatic activity, a flexible trying out of different stories or perspectives until you find one that works for you. As Phillips freely admits, this redescription—and perhaps redescription in general—might be naïvely wishful, not a bending of reality but a flight from it.

Freud’s biggest contribution to psychoanalytic thought might be his portrait of a persecutory, enigmatic, and disturbing unconscious. For Rorty, the Freudian id is another God term, a bad-faith bid to “delegate and outsource our purposes and our imagination and our intelligence to something beyond ourselves,” as Phillips puts it. Rorty, he writes, prefers to envision the unconscious as a team of partners or interlocutors, all of them “really useful, helpful and informed.” The prospect delights Phillips, but he’s skeptical: Does pragmatism’s redescription merely baffle our efforts to understand and transform our darker impulses? It’s when we refuse to face what we really want, he worries, that we grow pliant and manipulable, vulnerable to the lure of instant gratification and denied the chance to make something tonic out of our frustration.

Freud theorized that our lives are a project of tempering and downgrading desire, an ongoing compromise between fantasy and reality. By contrast, Phillips writes that the Rortian seeks “the most inclusive conversation possible” with our unconscious selves, one that “will further and proliferate our purposes and increase our sense of autonomy.” Strikingly, we should try to “proliferate” our purposes, not just advance them. If the father of talk therapy aimed to mitigate our wanting’s intensity, Rorty sought to intervene in its monomania. Phillips lays this out in “Too Bad, or On Seeing the Worst,” a chapter about an essay, by the Romanian author Emil Cioran, speculating that our elemental self, our “daimon,” might never have wanted to have been born in the first place. A Freudian might ask, lugubriously, how we might endure such pain. Phillips seizes the opportunity to wonder what we might gain from expressing a permanently unattainable desire. (“Having been born,” he writes, “is the one problem we can never solve.”) Perhaps, he offers, a loosening is possible—some breathing room, some permission to look around at what else might appeal. Via Rorty, he invites us to consider that we can desire many things and to live in a way that tests this hypothesis, releasing ourselves from the stranglehold of our single-minded obsessions.

“We have ourselves put the authorities deep down inside us,” Phillips writes in “The Life You Want.” In “Against Self-Criticism,” a 2015 essay for the London Review of Books, he picks a fight with the Freudian superego, whose ceaseless opprobrium, he claims, objectifies the rest of the psyche, reducing it to a single blameworthy victim. In fact, he writes, there is more to our inner ensemble than convict and executioner, or prisoner and despot. Each of us contains a “repressed repertoire” of “fragmentary alternative selves,” Phillips proposes. “Where judgment is, there conversation should be. Where there is dogma there is an uncompleted experiment.” Instead of letting your superego browbeat the other dramatis personae into submission, Phillips intimates, you should emulate a podcast host, moderating a respectful discussion among your mental parts.

His ideal of the psyche, in which all self-fragments get a hearing, can be extrapolated onto a society whose members are free to debate one another as they decide their paths forward. In his book “Equals,” he writes that “being listened to can enable one to bear—and even to enjoy—listening to oneself and others; which democracy itself depends on.” Psychoanalysis is misnamed as a “talking cure,” he submits. Really, it is a “listening cure.” Unsurprisingly, one of the political forms he’s most interested in is the relationship between analyst and analysand.

Self-criticism, Phillips writes in his L.R.B. essay, is “our most unpleasant—our most sadomasochistic—way of loving ourselves,” an attempt to win over the authorities when we fear we can’t otherwise live up to their expectations. In his telling, the patient often wants to comply with the heroic, omniscient analyst in order to avoid thinking for herself; the analyst must guard against this dynamic and against his own desire to dominate the patient. For Phillips, analysis is meant to help us “with our idealizations, with our craving for authority, our wish to idolize and be controlled.” The threat is that the analyst instead comes to resemble the superego, a “boring and vicious soliloquist with an audience of one.”

In “The Life You Want,” Phillips’s anti-authoritarian tendencies motivate him to rescue the idea of resistance, which in psychoanalysis refers to the conscious and unconscious strategies that patients use to impede the therapeutic process. “Resistance,” the volume’s culminating essay, notes that the analysand may have healthy reasons for evading her desires—she may be hoping to preserve a cherished value, for example—and that resistance can prolong and thus enrich the work of the cure.

This last argument enacts a familiar rhetorical move. Phillips often takes something apparently undesirable, such as guilt, and reframes it as a prelude or a precondition, a way station in a necessary developmental process. (Recall how he creatively redescribed frustration as the midwife to “realistic satisfaction.”) But his defense of resistance ultimately settles into a different shape and leaves him opposing the priorities of traditional psychotherapy. Phillips does not, finally, claim that recalcitrance on the couch crystallizes a patient’s understanding, thereby reducing her suffering. Resistance may not reduce her suffering at all. Rather, it demonstrates that she will proceed on her own terms and in her own time. Resistance “is integral to our singularity,” Phillips writes; the opposite of “defeatedness,” it’s a step toward “following one’s inclination and curiosity and refusing to be intimidated.” Here, departing from Freud, he casts freedom as more curative than the truth.

What do we need psychoanalysis for, then? For Phillips, the answer comes back to the intricate turnings and archeological layers of desire. Rorty believes “that we are good at knowing what we want,” Phillips writes, a contention that erases our ambivalence and underestimates our “need for safety.” Moreover, he claims, the Rortian vision of desire is informed by a shallow and too innocent view of the unconscious. Insensible to our Stygian instincts, pragmatism is always threatening to shade into permissiveness, a “kind of capricious, impulsive egotism.” It’s true that, without Rorty, Freud can appear “omniscient and impoverishing.” But without Freud, Phillips suggests, Rorty can’t surface the sunken richness of our wanting, its destructiveness, its haunting strangeness. Pragmatism fails to listen to desire. As a result, an essential texture of life escapes its grasp.

Like monogamy and infidelity, or our lived and unlived lives, psychoanalysis and pragmatism need each other. The plenitude, variety, and pluralism that are the highest values of liberal democracy require the force and insight of the psychoanalytic tradition, and vice versa. It’s unclear, though, that any of these pairs can be fully reconciled. The best case, Phillips implies, might be a conversation—not the idealized sort that results in unanimity or even acceptance, but a realistic one that grants the participants their full difficulty and irrationality and acknowledges that alignment might remain out of reach.

Still, the fantasy of a more perfect union persists. In one chapter of “The Life You Want,” Phillips describes the Freudian dream work. During the day, he explains, “we unconsciously pick things out that will be used in the making of our night’s dream.” This idea, that our unconscious gathers material during the day to dream with at night, suggests that what Rorty wants for us—to proliferate our purposes, to look around at what else we might want—is, in Phillips’s reading of Freud, already ours. By subjecting our inner worlds to such devoted scrutiny, the author of “The Interpretation of Dreams” emphasizes, in Phillips’s words, “the sheer scale of our interests,” the possible lives we formulate even when we don’t realize we’re doing so. “The Life You Want” is itself a sort of dream work, which synthesizes opposing elements into a poetic, if wishful, whole. ♦