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Ann Napolitano toiled in obscurity for years. Novels went unpublished; agents turned her down. She found recognition with “Dear Edward.” Then came the call: “Hello Beautiful” was the 100th pick for what is arguably the most influential book club in the world.Listen to This ArticleTo hear more audio stories from publications like The New York Times, download Audm for iPhone or Android.Maybe it was fate, maybe it was the meddling of a higher power with a wicked sense of humor. Either way, Ann Napolitano was taking out the garbage when Oprah Winfrey called to tell her that her novel, “Hello Beautiful,” is the 100th selection for what is arguably the most influential book club in the world.Napolitano was so afraid of losing the connection that she stood stock-still in the tiny vestibule of her Park Slope apartment building, clutching her bag of trash, for the duration of the 27-minute call.To be clear, we’re talking about Oprah’s Book Club — the O.G. reading group, trusty launching pad to the best-seller list and sourdough starter for dozens of iterations, celebrity sponsored and otherwise. Yes, Booktok is nipping at Winfrey’s heels, especially where young readers are concerned, but her endorsement is still a golden ticket.In the 26 years since Oprah’s Book Club announced “The Deep End of the Ocean” as its inaugural pick, the literary world has adjusted to the internet, electronic readers, smartphones and social media. Imprints closed, publishing houses consolidated, bookstores sprouted coffee shops and stopped selling CDs — and, through it all, the club established itself as a force, burnishing the careers of Wally Lamb, Cheryl Strayed, Lalita Tademy, Uwen Akpam, Isabel Wilkerson and Ta-Nehisi Coates, to name a few.Its machinations are still shrouded in mystery. Boxes of anointed books arrive at stores the day before a title’s publication date, to reduce the risk that customers will catch a glimpse of the club’s signature seal on a cover. Authors, agents and publishers are asked to sign nondisclosure agreements.“Hello Beautiful,” Napolitano’s fourth novel, came out Tuesday from The Dial Press and Winfrey announced it as her 100th book club selection on “CBS Mornings.” Only now, almost five months after Napolitano’s conversation with Winfrey, can the author share the news with her sons, who are 13 and 15.So how did “Hello Beautiful” land on Winfrey’s radar? And what was it like for Napolitano to get the nod? The short answers are simple and obvious (It’s a great book! She was thrilled!), but the expanded versions prove the equalizing power of a good story.Sitting in front of a lush Hawaii hillside that looked like a fake Zoom background but definitely wasn’t, Winfrey talked about the challenge of finding her 100th pick. The symbolic weight of it was on her mind. She wanted to find a book that would engage “every different sector of the population,” one she could recommend from an “authentically enthusiastic space.”“I went through many, many, many books, reading two and three at a time,” Winfrey said, projecting her familiar voice over the sound of rowdy bird song.“We’re separated from the world by our own edges,” Charlie Padavano says to one of his daughters in “Hello Beautiful.” He continues, “We’re all interconnected, and when you see that, you see how beautiful life is.”“I continue to choose what I love,” said Winfrey, pictured here with Ta-Nehisi Coates, author of “The Water Dancer,” her 81st pick. “I continue to be motivated by what touches my own spirit, what I think is going to allow people to sense a vulnerability in the characters, in whatever the narrative is, that opens the aperture for greater possibility for people.”Michele Crowe/CBS via Getty ImagesNone of the candidates had the universal appeal Winfrey was looking for.The vast majority of prospective titles go through a vetting process after publishers and agents present them to the book club, but “Hello Beautiful” took an unusual path. Winfrey’s friend, Richard Lovett, co-chairman of Creative Artists Agency, mentioned that Michelle Weiner, the co-head of CAA’s books department, had a novel she thought Winfrey would be interested in.“Every time somebody suggests that, it’s never true. It’s never something I actually want to read,” Winfrey said. “I was like, OK, send it to me.”She devoured “Hello Beautiful” on a rainy day in front of her fireplace, curled up with a blanket and her dog. She said, “I was like 30 pages in and said, OK, this is the book. You cannot read it without being opened. It just opens you in ways you didn’t know were closed.”The novel follows four sisters — Julia, Sylvie, Cecilia and Emeline Padavano — through decades of love, loss and (major) secret keeping. One falls in love with another’s ex-husband and the fallout is as complicated as you’d expect; somehow Napolitano persuades you to leave judgment at the door. The prevailing message is about the indomitability of family.“Not since Jo and Meg and Amy and Beth have we seen sisters like this, with this kind of connection, and written so vividly that you feel like you’re in that home,” Winfrey said. “You’re experiencing life with them. I am telling you, the ending? I mourned. What an extraordinary writer Ann is.”“It financially changed our lives,” Napolitano said of the sale of “Dear Edward” in a heated auction. “We bought a bed. That was the only thing we bought. My husband and I needed a new bed; my bed was from my parents’ house. I was 46 years old.”Elinor Carucci for The New York TimesThe iconic talk show host isn’t your average bookworm, but when she starts talking about what it’s like to fall in love with a novel —“Something starts whispering to me,” Winfrey said, “and I want to know more and I want to know more and I want to know more.” — it’s hard to tell the difference.“What I’m always trying to do is allow people to be lifted by the story somehow, and to see themselves — the people they know, their life — and come away feeling more connected,” Winfrey said. “Ann is one of those authors who’s able to do that without wearing it on her sleeve, without putting it out there in such a way that you feel preached to.”Napolitano’s third book, “Dear Edward,” was a best seller, a Read With Jenna pick and the basis for an 10-episode Apple TV + series starring Connie Britton. The book has sold nearly 400,000 copies.But until “Dear Edward” sold in a 10-imprint auction in 2018, Napolitano’s career was rife with rejection and disappointment. She wrote two novels that never sold. Her father was so concerned about her prospects that he paid for a full-day career test that flagged her potential as a park ranger.Napolitano struggled with depression. After being turned down by 80 agents, she signed with one who, sadly, died a few years later. She juggled a series of jobs — teaching, editing, corporate and educational writing, working as a personal assistant for Sting and Trudie Styler — while carving out short windows of time for her novel in progress. She couldn’t afford child care. At one point, Napolitano and her husband, Dan Wilde, had no health insurance. Her second published book, “A Good Hard Look,” (2011) took seven years to write, and “Dear Edward” (2020) took eight.“I’ve always had low expectations,” Napolitano said during an interview in a conference room at Random House. “Everything went so slowly or badly that all I wanted was a chance to do it again. I have to keep writing. I wasn’t ever counting on success.”Getting the call from Winfrey was, she said, “one of the most exciting things that’s ever happened to me in my life. I felt like I went into full menopause because my whole body system was just adrenalized and it was so crazy.”Napolitano was both tickled and horrified that, while she was reeling from the news, Winfrey launched into a series of questions about her writing process: “In that moment I was like, This is mean! That Oprah Winfrey thinks she can call you and expect you to have an intelligent conversation with her with no warning!”Napolitano started working on “Hello Beautiful” during the early days of the pandemic lockdown. “I was trying to find connection and love, and I needed that house with those loud sisters,” she said. “It really did feel like I needed this book.”Elinor Carucci for The New York TimesShe remembered how, at the end of their phone call, Winfrey said, “Writers are my rock stars and you’re a rock star.” Still shaky with disbelief, Napolitano unloaded her trash and walked a block to feed the meter in a two-hour parking lot. It was Oct. 20, 2022, the eve of her 51st birthday, the kind of crisp afternoon that lights Brooklyn like a movie set.Napolitano’s agent, Julie Barer, and her editor, Whitney Frick, had already heard from Winfrey’s team and were waiting for Napolitano to get the news. “I was running to my kids’ school and Julie texted me and said, ‘She called Ann!’ And I knew exactly what that meant,” said Frick, who is vice president, editor in chief at The Dial Press. “It’s really fun when good things happen for good people.”Barer, who is a partner at The Book Group, said,“Ann is extremely humble and hardworking. She’s no drama. She has an enormous heart and a tremendous capacity for compassion, and I think she brings that to her writing — about the messiness of relationships, and about forgiveness and empathy. It’s not like she’s Pollyanna; she’s not saying it’s all going to be great. Just that it’s going to be OK, and we’re in it together.”The three of them celebrated with a three-way chat. Then Napolitano finally went home and told her husband — who never second-guessed her writing career, even during lean times — why it had taken her so long to dispose of the garbage.“Ann walked in wearing a coat and said, ‘Oprah Winfrey just called me on my phone,’” Wilde recalled in an email. “Her eyes were wide with adrenaline, a contrast from her default steadiness. The first thought that came to mind was ‘Yeah, that makes sense.’”He’d seen how “Hello Beautiful” had overtaken Napolitano. Writing “Dear Edward,” she’d said, had been like entering a separate world, happily, then leaving when she felt like it. The Padavano sisters took a different approach: they occupied Napolitano, demanding attention, bringing their saints, their coffee and their chaos.“It was a very intense experience,” Napolitano said. “The story raced out of me. It was like holding onto the fender of a car, being banged across town.”Napolitano started “Hello Beautiful” in April 2020, the loneliest chapter of the pandemic, a time of fear and isolation. It was also the month her father died.“We weren’t able to see him when he was dying and we weren’t able to gather, like so many people,” Napolitano said. “I was trying to find connection and love, and I needed that house with those loud sisters. It really did feel like I needed this book.”Winfrey echoed a version of the same sentiment. “I felt less alone because of books during that period of being isolated,” she said, describing how, “as a girl growing up in Mississippi and Milwaukee, all the times I felt so removed and not valued, it was books — “A Tree Grows in Brooklyn,” in particular — that made me feel that I was connected to the world.”She went on, “And so, in the beginning was the word. The power of the word to help transform our own emotions and our own belief in what’s possible for us? I don’t think anything transcends that.”Audio produced by More