Actors and Actresses

Listen to This ArticleAudio Recording by AudmTo hear more audio stories from publications like The New York Times, download Audm for iPhone or Android.On a recent summer afternoon, Whoopi Goldberg led me to her backyard so I could see her plants. Goldberg, a native New Yorker, lives in New Jersey, in a gated community previously inhabited by Thomas Edison and the Colgate family, of toothpaste fame, which means her garden is measured not in yards but in acres. In the greenhouse there was a pineapple plant, grown from cutting off the top of the fruit; around the corner were the vegetables — tomatoes, green peppers, eggplants. Not that she eats them, she said, but they’re nice to have around. In one corner of the yard, flowers in Crayola shades grew next to a small sign: Emma’s Garden, named for her mother. Clusters of grapes dripped from gnarled vines, and garden gnomes stood watch all over the place. As we meandered, I joked that I felt as if I were in the Garden of Eden, and I asked her if she ever felt like God. “Well, yeah,” she responded matter-of-factly, “but I’ve played God so often that it’s sort of understandable that I would.” As with the Lord herself, Goldberg appears to everyone in a different way. Someone who has found her through “The Color Purple” or “Ghost” or “Sister Act,” her three best-known films, believes her to be a bona fide movie star with hazardous levels of charm. A person who recognizes her from the list of 17 people who have an EGOT — an Emmy, a Grammy, an Oscar and a Tony — probably knows that her roles swing from the very good to the shockingly bad, her résumé stacked with weighty achievements but even more blunders. A person who thinks: Whoopi Goldberg? You mean that surly lady on my TV in the morning? That is a regular watcher of “The View,” the daytime talk show that Goldberg has moderated for 15 years. And the person who considers Goldberg an unrecognized genius who has managed a one-of-a-kind, first-of-its-sort, decades-long career with dreadlocks on her head, no eyebrows on her face and her foot in her mouth? She knows Goldberg has actually played God only twice, but isn’t about to correct her. Though Goldberg, somewhat famously, loves living alone — a 2016 interview with her, published in this magazine, went viral for Goldberg’s assertion that, after three marriages, she knows she doesn’t “want somebody in my house” — she had rare houseguests that June afternoon. Alex Martin Dean, her daughter, and Dean’s children streamed in and out of the kitchen, draping themselves over one another as they stood around the kitchen island, bare except for a box of Popeyes and a script for “Harlem,” the Amazon TV show in which Goldberg has a small role. One of the grandchildren, Amara Skye, who had recently completed her celebrity-relative tour of duty and filmed a reality show, waved hello. (Called “Claim to Fame,” it was a show in which 12 relatives of celebrities moved into a house and had to guess their opponents’ family connections.) Skye’s daughter, Goldberg’s great-grandchild, Charli Rose, was around somewhere, watching TV. Tom Leonardis, the president of Goldberg’s production company, milled between rooms, finalizing travel plans. Despite indications toward cliché (have you heard the one about the old unmarried woman who lives alone with her cat?), Goldberg is perennially cuddly. Her skin is smooth, her cheeks juicy like a baby’s, even at 66. She lives every day like the Sabbath: When she’s not working, she told me, she sits around her mansion, moving from one room to another. Those rooms have the overstuffed charm of an antiques shop but the orderliness of the Met, with a dash of celebrity-bus-tour glamour. In the foyer stands a bowling pin painted with the image of Deloris Van Cartier, her character in “Sister Act”; a white grand piano covered in framed family portraits dominates her living room. On each floor of her house, there is a different photograph of Goldberg with the Dalai Lama. As we ate lunch in the kitchen, our plates laid atop a spotless white tablecloth with the Seven Dwarfs chasing one another around the trim, our backs pressed against the face of a cowboy embossed into the chair. A Kit-Kat clock shifted its eyes and tail toward me, while a genteelly dressed Black family encouraged me to “Choose Pepsi!” Over Goldberg’s right shoulder, I could see a panel from one of the late-19th-century Darktown Comics depicting a “coon club hunt.” “Uh,” I stammered, taking it all in. Little black sambos hanging on the walls watched us eat our mozzarella. “Have you always had these decorations?”Goldberg dipped her fork into her rice. “I love it because I don’t ever want to forget what it looked like, and what it is,” she said. Though she quit smoking 10 years ago, her voice is enticingly gritty, gravel topped with whipped cream. “We can do a better job, but this was the norm.” When I said that, for some people, it was still the norm, she replied: “In the past, I could understand, because they didn’t know any better. But people are willfully ignorant now.” Throughout her career, Goldberg has taken it upon herself — whether as a comic, or a social critic on “The View,” or the author of “Is It Just Me? Or Is It Nuts Out There?,” her ode to public civility, or even a producer of films like the forthcoming “Till,” about what happened after Mamie Till decided to send her son away for the summer — to temper that ignorance. In a September screening for the film, in which Goldberg plays Mamie’s mother, she spoke to the necessity of telling these stories: “You can’t get pissed off when people are stupid when you have the ability to make them smarter.” ‘I don’t think anybody had ever said or led me to believe that I could be part of this country that I was living in.’Which makes things all the more thorny when she says something out of pocket or just plain wrong. This is undoubtedly one way people come to Goldberg, through the controversies that flare up over comments she makes. The most recent one unfolded this winter, during an episode of “The View” about a school board’s decision to ban the book “Maus,” when she claimed that the Holocaust was not really about race because both Germans and Jews were white; she tried to apologize but ended up doubling down on the comments during an appearance that evening on “The Late Show With Stephen Colbert.” (The next day, she apologized on “The View” and was suspended from the show for two weeks.) Goldberg told me that she initially thought my interview request was a joke, or a grave misunderstanding. Then she thought about how long she’d been working — “Till” is the 100th or so film she has appeared in over 35 years — and figured that was probably worth something. She’s not wrong. But perhaps even more impressive is that her career has endured despite her habit of making people uncomfortable. Goldberg has always said what is on her mind, and this elicits a special frisson: Will it be wild and thought-provoking or wild and offensive? Most celebrities feed us bland platitudes and workshopped comments. Goldberg has never held anything back. She knows that this is part of her legacy, but also what it can cost her. When I arrived and asked her how she was doing, she replied simply, “Nobody’s mad at me today.”Goldberg has never wanted to be called “African American.” When she became famous, one of her first controversial positions was rejecting the label. To her, the prefix denotes an unnecessary difference, a verbal “where are you really from?” In her second book, 1997’s cheekily titled “Book,” she writes:I refuse to be labeled an African American. When you tell the story of this country, I’m part of the fabric. Black people, stop trying to identify elsewhere. This is yours. People in the South got their legs chewed off, got hit with [expletive] fire hoses, got their children blown up, got yanked, burned, hanged and sliced so that you wouldn’t have to pretend you were from someplace else. So that you wouldn’t have to say, “No, I’m not entitled to this.” Well, [expletive] that. You’re entitled to all of it. Take it. It’s ours. With her fame came the pressure of representation, the weight of a race on her back. But the flip side of Goldberg’s venerated authenticity is a rejection of respectability. Her preternatural confidence, and an unshakable sense of belonging, were there from the very beginning.Goldberg was born Caryn Johnson in New York City in the fall of 1955. She grew up in Manhattan in what is now known as the Chelsea-Elliott Houses with her older brother, Clyde, and mother, Emma. The three were very close. (Emma died in 2010; Clyde died five years later.) In “Book,” she writes that her childhood was largely sheltered from racism; the civil rights movement “didn’t resonate the way it did in the rest of the country. There was no place that was restricted to me.” The families in her housing development were uniformly poor, but diverse in races and ethnicities, making it the sort of place where you had to know a few words in multiple languages to ask if a friend could come out to play, and where if you were caught acting up, somebody’s mother would deal with you until your own mother got home. As a kid, Goldberg performed in community theater and spent hours gorging on old movies with stars like Carole Lombard and Bette Davis. But her primary interests were otherwise books and sports. (“The subtle art of being a girl evaded me,” she told Roger Ebert in 1985.) One day, John F. Kennedy campaigned in her neighborhood. People from all over the city came to watch him speak, but Goldberg took the matter quite personally: The future president of the United States cared about her. Later, when she heard his Inaugural Address — “ask not what your country can do for you” — she realized that he was speaking to her too. “That was the first time I thought, Oh, I’m part of this,” she said. “Because I don’t think anybody had ever said or led me to believe that I could be part of this country that I was living in.” After struggling through school — her test scores were so low that teachers told her she was intellectually disabled — she dropped out of high school after one year. (As an adult, she was diagnosed with dyslexia.) Her mother, a Head Start teacher, cut her a deal: She could leave school, but she would have to participate in some sort of cultural enrichment, “just to keep my mind juicy.” Goldberg cobbled together her own education: going to the American Museum of Natural History and learning about the solar system and paleontology, or heading to the New York Public Library for an exhibit on Lewis Carroll and “Alice’s Adventures in Wonderland.” Her mother would quiz her when she got home.Goldberg in 1985.Roger Ressmeyer/Corbis/VCG via Getty ImagesBefore she turned 25, Goldberg had become addicted to drugs, gotten clean, married her drug counselor, given birth to her daughter, Alex, and divorced. After her marriage ended, Goldberg and Alex moved to San Diego. She earned money working as bricklayer and a morgue beautician, and she found some success in repertory theater and improv groups. It was there that she became Whoopi Goldberg, a name that combined her radical embrace of flatulence and an alleged Jewish ancestor. (In a 2006 episode of a genealogy show hosted by Henry Louis Gates Jr., Goldberg was not shown to have one.) Eventually, she and Alex moved to Berkeley, where Goldberg started to develop characters for something more ambitious.“The Spook Show,” equal parts Lenny Bruce and Moms Mabley, premiered soon afterward. In it, Goldberg transformed into different characters — a Jamaican nurse, a surfer chick, a woman with a physical disability — each given a monologue laced with surprising, if occasionally unsubtle, wisdom. She put the innermost thoughts of her characters on display, introducing her audience to the sorts of people they didn’t know but probably passed every day. Whoopi Goldberg, an Outspoken StarThe comedian and co-host of the ABC talk show “The View” is known for her provocative opinions — and controversies.‘The View’: Since 2007, Whoopi Goldberg has been the often-irascible moderator on the daytime talk show, helping it become one of the most important political TV shows in America.Holocaust Comments: Earlier this year, Goldberg was suspended for two weeks from “The View” after she said repeatedly that the Holocaust was not about race. She later apologized.On Living Alone: After three marriages, Goldberg told us in a 2016 interview that she knows she doesn’t “want somebody in my house.”A Decades-Long Career: In 2019, the Times podcast “Still Processing” discussed  Goldberg’s career, from her days as a boundary-pushing comedian to her role as professional curmudgeon on “The View.”After some local success, Goldberg and her partner at the time took the show on a short tour of the United States and Europe before she parked it at the Dance Theater Workshop in Manhattan. The show was a word-of-mouth phenomenon, and Goldberg went from performing in front of only a handful of audience members to packed houses that included many celebrities. One evening, the director Mike Nichols found Goldberg backstage and, with tears in his eyes, told her he would produce anything she wanted. It was one of the great before-and-afters of her life: Nichols moved the show to Broadway, where he produced it and looked after her, helping her forge connections in the theater community. Goldberg eventually turned the show into her first comedy album, which won a Grammy in 1986.In 1984, Steven Spielberg, just off “Raiders of the Lost Ark” and “E.T.,” was looking to cast the lead role for his next film and asked Goldberg to perform “The Spook Show” at his personal theater in Los Angeles for him and a few friends. Backstage, Goldberg peeked around the curtain and saw Michael Jackson. Soon after, Spielberg offered her the lead role of Celie, a downtrodden woman who has to learn her own strength, in “The Color Purple.”A critical and commercial success, the film was nominated for 11 Academy Awards, including a best-actress nomination for Goldberg. Roger Ebert, who named it the year’s best film, called Goldberg’s role “one of the most amazing debut performances in movie history.” But even after this triumph, the film industry didn’t quite know what to do with her. Was she the next Eddie Murphy (wily and cunning, in films like “The Associate” or “Burglar”) or a Black woman hired to teach white people important lessons (“Clara’s Heart”) or the person to call when Shelley Long was unavailable (“Jumpin’ Jack Flash”)? She had been tasked with spit-shining the junk given to her — in “Theodore Rex,” a film she was contractually obligated to complete, she played a detective assigned to an investigation with a dinosaur — but she still became a punchline: The comedian Sam Kinison joked in an interview that Whoopi Goldberg is what happens when “a nation is afraid to hurt a person’s feelings.” Goldberg in “Jumpin’ Jack Flash” (1986).Everett Collection“Clara’s Heart” (1988).Everett CollectionIt wasn’t just that she was Black and a woman; it was that no one knew exactly what kind of woman she was. Dreadlocks, Jewish last name, old-man clothes, a smile that could blow out an electrical grid. Did she have sex appeal, and what would the industry do with her if she didn’t? Worse: What would it do with her if she did? Even in her turns as a romantic lead in films like “Made in America” or “Fatal Beauty,” where she played opposite white men, her characters always stayed chaste.Soon after the success of the “The Color Purple,” Goldberg learned of a forthcoming adaptation of “The Princess Bride” and wanted to audition for the title role. She was laughed away. The matter came up in a 1997 Playboy interview: “I said: ‘But the book is about a princess who doesn’t look like anybody else, who has a very different attitude. So why not me?’ It hurt my feelings because I thought, Are you telling me that because you think I couldn’t be a princess that all these other doors are going to slam too? Basically, yes. So I took the stuff that nobody seemed to have a problem with me doing.”Goldberg says she couldn’t get an audition for “Ghost” until the film’s star, Patrick Swayze, threatened to pull out unless she was given a chance. She went on to win an Oscar for her performance as the psychic Oda Mae Brown. Lost somewhere in the confusion about what to think about Goldberg was her actual talent, especially when paired with material that treated her as more than a visual gag, the humor rooted in the mere fact of her presence. The 1990 drama “The Long Walk Home,” released around the same time as “Ghost,” is a hidden gem in Goldberg’s oeuvre. She plays a maid who, during the bus boycott in Montgomery, Ala., has to walk to and from her job. Gone is the sass and the racial bewilderment required of many of her post-“Color Purple” roles, and what’s left is a soft-shelled tenderness, her face — the subject of so much derision — conveying a steady sense of hope even amid the dramatic violence.In “Book,” Goldberg wonders about whether such a role could promote stereotypes. When she filmed “The Long Walk Home,” she fell into the trap of contemporary confidence: She briefly believed that she would’ve made different choices if she had grown up in the South during the civil rights era. But she started talking to the Black women who worked as nannies and maids at that time, and they sobered her up. “ ‘You wouldn’t have done it any differently,’” one of the women told her. “ ‘When we were coming up, if you made any noise, they’d hang you.’” Goldberg realized that she didn’t know her own history well enough if she could fantasize about alternatives. These women became her heroes. She writes: “They held their breath and their tongue until the world caught up to what was right. They kept the family together — theirs, and the upper-class white families they were working for. And they survived. So what the hell was wrong with playing them? Nothing. Nothing.” Goldberg took over the lead role in “Sister Act,” the fish-out-of-water comedy about a lounge singer forced to hide out in a nunnery, after Bette Midler, for whom the role was originally written, turned it down. It was a smash success, and the rapidly made sequel, “Sister Act 2” (1993), briefly made Goldberg the highest-paid woman in Hollywood, at a reported $7 million. But the fulfilling roles were still scarce. Goldberg worked steadily — occasionally appearing in schlock but always appearing in something. She M.C.ed the Grammys once and the Oscars four times, her humor inflected with just enough severity so viewers could never quite relax. (In 1994, at the Oscars: “Lorena Bobbitt, please meet Bob Dole.”) She had an ingenious short-lived talk show and a few stand-up specials on HBO that skewered Black anxiety and white nonsense. With Billy Crystal and Robin Williams, she repeatedly hosted the “Comic Relief” telethons to raise money for the homeless, the motley crew of comic do-gooders becoming incredibly close friends in the process. She was political and unafraid to be insolent where it counted, unmoved by expectation or custom. Crystal told me that once, Senator Edward M. Kennedy invited the trio to Washington for lunch to discuss federal aid on homelessness. Williams and Crystal arrived in suits, but “Whoopi was in a baseball-uniform top that said, in script across it, ‘Balls.’ And Ted Kennedy said, ‘Is that a team?’ And she said, ‘No, it’s a plea.’” Williams and Crystal grabbed each other’s hands under the table. (Kennedy laughed.)Goldberg with Billy Crystal and Robin Williams at a “Comic Relief” telethon in 1986.Agence France-Presse/Getty ImagesAnd then suddenly the work was gone. To this day, she is convinced that something she said had finally damned her, making people hesitate to send her scripts. Fifteen years after winning an Oscar, she was hosting the Universal Studios Hollywood theme-park tour.Despite her two-week suspension from “The View” early this year or, say, the outrage after Ted Danson, her boyfriend at the time, wore blackface to a roast of her in 1993, Goldberg thinks she has really been canceled only once. In 2004, she and a bunch of other celebrities gave remarks at a fund-raiser for John Kerry, then running to be the Democratic presidential nominee. Everyone took potshots at the incumbent: Meryl Streep wondered “which of the megaton bombs Jesus, our president’s personal savior, would have personally dropped on the sleeping families of Baghdad.” Chevy Chase got a round of cheers for saying, “Clinton plays the sax, John plays the guitar and Bush’s a liar.” John Leguizamo quipped: “Latins for Republicans? It’s like roaches for Raid.” Amid all this, Goldberg told a joke herself. The next day, a reporter named Deborah Orin published an article in The New York Post with the headline “DIRTY TRICK: LEWD WHOOPI BASHED BUSH.” The story referred to Goldberg’s remarks as an “X-rated rant full of sexual innuendos against President Bush.” Orin continued covering the story closely, as Republicans insisted that Democrats release the recording of the monologue that “turned Bush’s name into a crude sexual joke.” As other outlets picked up the story, more performers were also called out, but the focus and furor were trained squarely on Goldberg, then a darling of the Democratic Party and a close friend of the Clintons’. Goldberg’s career went dark. SlimFast, the diet-in-a-can brand for whom Goldberg had been the spokeswoman, dropped her. Friends stopped associating with her in public. She was disinvited from the Democratic National Convention. But the worst part of all? Nobody ever printed the joke.“You know why they couldn’t print what I said?” Goldberg asked me. “Because I didn’t say anything that was bad.”It was a sweaty August afternoon, and we were at her summer home on the coast of Sardinia, in Italy, eating at a table topped by a lazy susan as wide as a hula hoop. The property has two houses: one for Goldberg (remember: “I don’t want somebody in my house”) and one for guests. She decided to buy the place after spending a single night, waking up to the sight of the sun pulling itself from the horizon over the Tyrrhenian Sea. Goldberg is an avid real estate browser; she refers to it as her porn. When I first met her, I asked which was her favorite: Zillow? Realtor.com? “Christie’s,” she replied. She took a beat, then without energy or interest, recited part of the joke as she remembered it: “I love bush. Somebody’s giving bush a bad name. So let’s take him out and everybody get out and vote.” Her eyes flicked over to me, and the monotone switched off. “I might’ve said, ‘[Expletive] — so get out there and [expletive] vote.’ But to hear them talk about it, I was disgusting.”Over the course of reporting this story, the magazine’s research department dug up the actual text of her joke, and it was as tame as she remembered it; There wasn’t even any cursing. “When Bush comes to shove, don’t whine,” she told the crowd. “Vote Kerry. And that’s why I’m here tonight. Because I love bush. But someone’s giving bush a bad name. Someone has tarnished the name of bush. Someone has waged war, someone has deliberately misled the country, someone has attempted to amend the Constitution, all in the name of bush. The bush I know and cherish would never do such things. My bush is smarter than that. And if my bush is smarter than that, you can understand just how dumb I think that other bush is.” She closed by saying, “Vote your heart and mind, and keep bush where it belongs,” pointing at her crotch.Hearing her riff read back to her, Goldberg said, gave her something she had wanted for 20 years: proof. Her remarks weren’t obscene — at least, no more than anyone else’s. She wasn’t crazy in her self-defense and insistence that she hadn’t done anything wrong. The only thing she was guilty of was being funny, and then unfairly maligned.In Sardinia, I asked her whether she thought the quick drop was just the way Hollywood worked, or was perhaps unique to anything about her. “Well, it’s unique to me, because I didn’t say any of the shit that they have accused me of saying,” she said. It’s not that she didn’t want to be called out for her actions; she just wanted to be called out accurately. “I mean, I did stuff” — her character on her short-lived sitcom “Whoopi” had a cardboard cutout of Bush that she routinely kicked down the stairs — “but I didn’t do what they said I did. And I will take anything that you’re mad at that I actually did. But you cannot accuse me of shit I didn’t do.” Here’s a small offering of things Goldberg has actually said, all over the past few years on “The View”: to let the football player Ray Rice defend himself against his wife (“I’m sorry, if you hit somebody, you cannot be sure you are not going to be hit back”), to cut Rachel Dolezal some slack (“If she wants to be Black, she can be Black”), to be crystal clear on the criminal charges against Roman Polanski (“I know it wasn’t rape-rape. It was something else, but I don’t believe it was rape.”). So yes, some of the backlash is warranted. Her otherwise generous and typically mainstream sensibilities — racism is bad, people should be kind — get gummed up. She has spent so much time avoiding becoming a role model that she seems to have forgotten the weight of her words, especially when standing at a pulpit before millions. She’s not always as precise as she should be — better if she had said “forcible rape,” or had noted that her understanding of race is not definitive — and her own cancellation in 2004 has made her almost too skeptical of judging other people. But she knows what it’s like to be misunderstood before you’ve even had a chance to explain yourself, and she is willing to be a dam against the tide of swift public opinion.‘She makes it look so easy, but I imagine that it has cost more than we would imagine.’“There’s a wider range of topics that she tackles every day, but the fearlessness and the fierceness hasn’t changed,” Crystal told me. “The compassion that she has for people, alongside the acerbic quality to intelligently go after people and sometimes make mistakes. She’s on the edge a lot, which is a wonderful place to be. She doesn’t back down.”Few among us could expertly navigate having to speak on topics as varied as “Miami School Board Rejects Sex-Ed Textbooks” to “Guest Brings Eggs to a Vegan Wedding” every weekday morning, for years, with a bunch of people hired to appeal to a different demographic from the one you’re in, and not end up on the wrong side of a comment. Her thoughts can be maddening in their simplicity, but expressing unvarnished thoughts is also increasingly rare. She’s not trolling; she’s just trying to stay true to herself, even when the moment demands that it’s better for her not to.In Italy, Goldberg told me that she had heard people describe her as an “O.G.,” but she didn’t know what it meant. I explained that it stood for “original gangsta.” “OK, well, that is true,” she allowed. “Everything I am saying and everything I’m telling you about myself should allow people to understand that I am an original gangsta, because gangstas just don’t care what you think.”The B-plot of a 2009 episode of “30 Rock” finds Tracy Jordan, a buffoonish comedic actor longing to be taken seriously, aiming for an EGOT. Jordan, played by Tracy Morgan, seeks advice from Goldberg, the first Black person with an EGOT. Goldberg won a Tony Award in 2002 for producing the musical “Thoroughly Modern Millie,” the 1991 best-supporting-actress Oscar for “Ghost” and a Grammy in 1986 for her comedy album. In the episode, when Jordan reacts with derision to learning that in 2009 Goldberg won a daytime Emmy for hosting a talk show, not a prime-time Emmy, she shrugs him off: “Girl’s gotta eat.”Previously, the EGOT achievement was an esoteric industry joke, a long-forgotten goal once set by Philip Michael Thomas, a star of “Miami Vice,” in interviews. Thomas was so committed that he had the letters engraved on a pendant that he wore around his neck, holding the goal close to his heart. (He has yet to win any of the awards.) But as the designation took hold in pop culture — after the episode, news organizations began to refer to it — a reverence for Goldberg crept in with it, as if people could finally understand her aptitude now that there was a yardstick with which to do so. In one of our conversations, I asked Goldberg what people misunderstood about her. Over her entire career, she responded, even now, people are shocked to find out that she’s actually talented: that she writes books and produces films, that she owns businesses, that she possesses any dramatic skill, that she’s not a daffy pothead who moves without intention or foresight, that her career did not come about solely through luck or by playing off white guilt. Even with the EGOT designation, and a peer group too small to fill the roster of a hockey team, some people continue not to take her seriously. She told me she wasn’t sure why, but we both knew the litany of possibilities, the problems people have had with her from the beginning.I noted how frustrating it must feel to have been underestimated for so long. “That’s a good way to put it,” she said, chuckling. Then she turned solemn, as if she were taking in what I said. “That’s a good way to put it.” On the set of “The View” in 2009.Steve Fenn/Disney General Entertainment Content via Getty ImagesWhen it comes to Goldberg’s peers, I think less of comedians and actors than I do music artists: women like Tina Turner and Donna Summer and Missy Elliott, who had clear visions to cut uncharted paths but were stymied by people who didn’t think they looked the part. About Elliott, the cultural critic Hilton Als wrote, in 1997, that the rapper-producer was one of the New Negroes, which he defines as “a woman who considers her marginal status a form of freedom, and a challenge — she takes the little she has been given and transforms it into something complex, outrageous and ultimately fashionable.”If enough people tell you that they have no idea what to make of you, no idea where you fit, next to that pain of rejection grows a thrill: If you’ve already discounted me, why limit myself? I like to think of Goldberg as a trickster: a person who eludes category by shifting unpredictably, upending expectation each time. She pushes up against social boundaries, turning them inside out and shaking out the dust. Take something as simple as her hair: Despite decades of complaints (and the ensuing ill-fitting wigs she has had to wear), she has never changed it, never opted for something more feminine, confident in the relationship between her sexuality and her androgynous appearance, even if the industry hasn’t been. “What fascinates me beyond the phenomenon of Whoopi’s persona is the way she has embraced the mainstream while remaining so radically herself,” the writer Ottessa Moshfegh wrote to me in an email. Her novel “My Year of Rest and Relaxation” featured Goldberg as a near-deity. “To me it’s very hopeful to see a consummate artist take the stage with such optimism and honesty. She makes it look so easy, but I imagine that it has cost more than we would imagine.”In my early 20s, I would take the B train from Prospect Park to the Upper West Side, where I would unleash my myriad anxieties on a junior therapist, because she was all I could afford at the time. She was beautiful and confident and told me she learned English by watching episodes of “Friends,” but the thing I hated most about her was that all she ever seemed to tell me was that I was normal. That wasn’t what I needed to hear. In fact, it was offensive. I had never aimed for normalcy, a land for middle children and people who knew how to drive — I liked feeling different from everyone else, and I had felt that way as long as I could remember. What I wanted was to feel OK about those differences, to feel their power instead of their weight.Assimilation is a grieving process: losing the very essence of you for the comfort of acceptance. That Goldberg has refused makes her a role model (even if she would hate that) for going against convention and relishing it. This summer, the comedian Jo Koy appeared on “The View” and was so thrilled to meet Goldberg that he cried on air. As a child, he stumbled across one of her specials on HBO and was transfixed by this woman who looked like nobody else in comedy. “You watch Whoopi, and you go, Oh, OK, you can be yourself,” he told me. Goldberg didn’t give us permission to be weird, but she made it look impossibly cool. The actress Mary-Louise Parker, who co-starred with Goldberg in “Boys on the Side” in 1995, has remained close with her. We talked on the phone for an hour. (“I know it sounds like I’m laying it on,” she said of Goldberg’s generosity. “But she was — she was in my son’s short film.”) Parker avoids social media and all celebrity news coverage, so I filled her in on some of Goldberg’s controversies over the past few decades. She was unmoved by other people’s opinions. “If a person has never done anything that offends anyone, or that nowadays in society you have to apologize for them, they are not being authentic,” she said. Abandoning herself would cause an almost physical pain for somebody like Goldberg. “The two are not compatible.”In Sardinia, Goldberg and I sat down to eat dinner with Leonardis, her business partner, who was staying in the guesthouse for a few days before visiting his fiancé in Bologna, and Paolo Alberti, a friend of theirs. Though the conversation leaned sophisticated — Leonardis and Alberti were going over every detail of a recent Dolce & Gabbana presentation — Goldberg punctuated it with short bits, animating whatever might be at her fingertips with funny voices and scenarios. When a gravy dish with tiny clay feet ended up in Goldberg’s hands, it came alive, arguing with her about where it belonged, telling her it could get its damn self to somebody else’s plate. After a fly landed in her drink, she gave us its inner monologues, compressing her voice into a squeak: Now the fly is donning his swim camp and getting ready for some exercise. Our companions, obviously used to this, laughed along, but I found myself totally enchanted. Goldberg didn’t give us permission to be weird, but she made it look impossibly cool. Ruth Ossai for The New York TimesAs the fly started doing laps in her prosecco — perhaps training for the Olympics — the phone rang: Alex called to tell her that Olivia Newton-John had died.Out of respect, Goldberg told her Alexa to play the soundtrack from “Grease,” explaining that it is her daughter’s favorite movie, hence the emergency call. Once, when Alex was young, Goldberg got John Travolta to meet them at Disneyland as a surprise. In her seat, Goldberg started re-enacting the dance moves from “Greased Lightnin’.” Leonardis and Alberti had returned to discussing fashion, so I had no choice but to join her, the two of us wordlessly dragging our pointer fingers toward an invisible audience, pumping each arm up and to the side. The next morning, news about Issey Miyake’s death broke moments after we had been talking about him. We were all disoriented by the coincidence, but Goldberg was clearly affected — she loved his clothes, which is why we were talking about him in the first place. And then it set in: Newton-John is one, Miyake is two. … “It’s always three,” Leonardis said. All eyes turned to Goldberg. “I’m not getting on the plane, I’m not getting in the car, I’m not getting on the Segway, I’m not doing anything today,” she responded.But eating, she decided, was safe, so we had one last lunch. While the groundskeepers, a married couple, tittered around, their golden retriever amused himself with an extremely squeaky ball. Goldberg took the bait: She became the dog. Her voice high and goofy, dog-Whoopi breathlessly recounted the pleasures of having balls on your face, then advocated playing with balls in general. Somehow it came out that Alberti had never seen the viral video of Eartha Kitt responding to the idea that relationships require “compromise,” so somebody pulled it up on a phone. Goldberg relished the rancor with which Kitt repeated the word, which was about a dozen disgusted times in under three minutes. “If a man came into your life, wouldn’t you want to compromise?” an off-screen interviewer asks Kitt. Her face twists into bewilderment and disgust. “A man comes into my life,” she responds, “and I have to compromise? You must think about that one again.” She laughs wickedly. Goldberg was pleased as punch. She reminded me of a kid encouraged to make their own fun, one who could find amusement with any toy. And away she went: Goldberg started her Kitt-themed variety hour. She taught us a bit of Kitt’s history — did you know that her two most popular hits, “C’est Si Bon” and “Santa Baby,” were released in the same year? — and did a rendition of “C’est Si Bon,” her voice in a different register of smokiness. And then she went back to the video itself, which goes viral every few years as a paean to independence, a rejection of the idea that an institution — that anything, really — can force you to conform to external expectations. Goldberg replayed it, this time folding her hand into a puppet, performing as earnestly as she would onstage. Her commitment made it feel real. “Compromise? What is compromising?” she made her hand say. “Compromising for what? Compromising for what reason? To compromise? For what?”Hair by Issac Poleon. Makeup by Mata Marielle.Ruth Ossai is a Nigerian British photographer whose work celebrates identity, particularly Nigerian identity, and culture. More