What does she have against bread?
“I love bread more than I love my children,” Ms. Brown said. She has three grown sons — Dylan, Dakota and Duke — with her husband, Steven Plofker, a real-estate developer with many projects in the area. Like Oprah, she shared a bread fantasy: “I would have crusty bread with steak tartare. Pizza. I think I would rather have bread than pasta. I like crunch.” And on it she would put?
“Butterrrr!” she said lasciviously, to shrieks of laughter from her colleagues. “I mean, why mess around with cheese?”
Ms. Brown sat on a leather sofa with her plump mutt, Biggie, at her feet, and shared that a tenant upstairs was Luke Parker Bowles, a film producer who is the president of the British Academy of Film and Television Arts and the nephew of Camilla, the Duchess of Cornwall. ”He just comes down nonstop,” she said. “It’s like a sitcom.”
When Mr. Parker Bowles indeed made an appearance an hour later, he called Ms. Brown “the kindest woman I know in this area code,” and along with Mr. Plofker, “the beating heart of Montclair.” They are active in the town’s philanthropy, and every Yom Kippur they have a break-fast party at their house attended by prominent locals like Senator Cory Booker, Stephen Colbert and the journalist Jonathan Alter.
Still, driving past the Whole Foods near Main Street in her Range Rover, Ms. Brown will say things like “I’m a suburban mom that goes to the grocery store.”
The couple’s newest baby is the George Inn, a 32-room boutique hotel, with rooms starting at around $200 per night and a library and lobby filled with pictures of famous Georges and Georgias: O’Keeffe, Hamilton, Harrison, George Herman Ruth Jr. (a.k.a. Babe Ruth), Washington, Jefferson from the TV program, Costanza (the two presidents Bush have not yet found their spots). It is the latest addition to a portfolio that has included retail, office and sports complexes, along with her namesake eyeglass line and nine books.
Back at headquarters, Ms. Brown’s phone beeped the opening bars of “(I Can’t Get No) Satisfaction.” She took the call, looking like a teenager in a white Brandy Melville T-shirt and black sweater, legs curled up under her in jeans with prefabricated holes.
On another board nearby were some of Ms. Brown’s favorite mantras, which she has had put on pencils, like “Be Who You Are” — “Everyone else is taken, you know,” she said, once off the phone — and “Focus On What You Do Like” and “Simple Is The New Black” and “Be Nice.”
“Duh. Hello?” Ms. Brown said. “Like, you don’t like something? Be nice.”
If this all seems terribly basic, consider how she amassed her fortune.
‘I’m Still Here’
Ms. Brown first moved to New York in 1980, the child of an amicable divorce in suburban Chicago (down the block, at one point, from Hugh Hefner and his ex-wife) who had gotten a degree in theatrical makeup from Emerson College after years of struggling with schoolwork. She lived with her boyfriend from high school, a photographer, in a one-bedroom apartment on West Fourth Street that cost $500 a month, maxing out credit cards and making cold calls to agencies and bookers.
Her ad in The Village Voice offering makeup lessons got one answer, from a preppily dressed man who said he was in a play and needed to look like a woman. “I was freaked out,” Ms. Brown said. “He dressed up in drag and then wanted me to teach him how to do makeup. I made a few bucks, but I didn’t put an ad in again.”
The makeup artists’ union helped find her some work, including assisting on “Saturday Night Live,” and within a year she got a good gig at Glamour magazine, but there was discouragement aplenty. “I had a hairdresser tell me I would never work in this town because I didn’t have a style, I didn’t have a thing,” Ms. Brown said. And now? “Well, I know he’s in Palm Springs and he’s got a salon, ha-ha, and I’m still here.”
If Ms. Brown had any look at the time, it was “Flashdance” meets Madonna, who worked out at her gym. She knew she disliked what was then modish: white skin, red lips and the practice of contouring to create cheekbones. “Just not necessary,” she said, though she admired the work of Way Bandy and Kevyn Aucoin, who “could literally paint a face. But the finished product is not a woman that walks outside. It’s being photographed. It’s not a real look.” She tried to conform and get along, watching once as Jerry Hall redid her own makeup for a Cosmopolitan shoot.
Ms. Brown got a break when an agent called to ask if she was available the next day to work with the photographer Bruce Weber. “I was a wreck,” she said. “I must have tried on 15 outfits because I wanted to just have the perfect cool when I walked in.”
She and Mr. Weber were a good match. “He didn’t want any makeup!” she said. “He wanted not to see anything.” Asked if she witnessed any bad behavior from Mr. Weber, who has been accused of sexual misconduct, Ms. Brown said, “Honestly, I grew up in the fashion industry, with photographers and assistants and male models and you know, the ’80s, everything just seemed like a big party. Which I really wasn’t a participant in because I either had a boyfriend or a husband.”
She was introduced to Mr. Plofker in 1988 by a friend over dinner at Raoul’s, a restaurant in SoHo. “All I can say is, ‘Boom,” Ms. Brown said. They talked nonstop, she remembered, then put the friend in a cab, then “talked for an hour outside my building.”
The next day, Ms. Brown was happy to find out that her new swain had a master’s degree from Harvard and was, like her, Jewish. “Then I realized his last name was Plofker,” she said. “But I married him anyway.”
After the newlyweds moved to Montclair and began raising a family, Ms. Brown started to tire of the fashion industry’s constant travel. She had fantasized about creating her own line. “My philosophy was women don’t need a lot of makeup, they just need a few things,” she said. “Clearly that’s not what happened to the billion-dollar brand.”
Its origin story is now part of corporate lore: the chemist she met during a Mademoiselle shoot at Kiehl’s, the 10 subtly colored lipsticks (including one named, conveniently enough, Brown) that sold 100 units their first day at Bergdorf Goodman in 1991.
Four years later, Leonard Lauder courted Ms. Brown and a business partner, Rosalind Landis, over grilled chicken, steamed vegetables, brown rice and wine on the terrace of his Fifth Avenue penthouse. “It was an out-of-body experience, to see Picassos and Dubuffets and everything there,” Ms. Brown said. As the sounds of the New York Philharmonic playing in Central Park wafted toward the sky, Mr. Lauder told her she reminded him of his mother, Estée.
“‘You’re beating us in all the stores, and I want to buy you,’” she recalled him saying. “‘What if I told you could do exactly what you love to do and want, and I would give you complete autonomy?’”
“I didn’t even know what autonomy was,” Ms. Brown said.
She added that her company’s reported selling price of around $75 million was inaccurate, but she doesn’t remember the precise amount. “Oh, it was a lot,” she said. “Yeah, I never had to work again.”
Mr. Lauder, she said, was supportive and always “very fatherly” with her. “Leonard used to tell me, ‘Don’t ask for permission, beg for forgiveness,’” Ms. Brown said. “That’s the way he ran the company.”
But she missed not being the boss, disliked corporate-speak — “things like ‘optimize!’ That just means ‘do it better!’” — and hated meetings. In the middle of one long, boring one, Ms. Brown took out a concealer she’d been given that was way too thick under the eyes. She put it all over her face, experimented and looked in a mirror. “It turned into a sheer product,” she recalled: the Retouching Wand, joining her much copied Gel Eyeliner and Shimmer Brick, a highlighter.
By 2010, Bobbi Brown Cosmetics was available in more than 980 doors and 56 countries. By 2012, there were over 60 freestanding Bobbi Brown Cosmetics stores worldwide. But in her later years there, Ms. Brown said she experienced more “aggravation,” like when she started a “JustBobbi” Instagram account. “I would always get in trouble,” she said. “Someone from corporate would always call down, you know, ‘What did Bobbi post?’ and I was like, ‘Guys, I’m a person.’”
Eventually such strictures began to chafe. “Look, anyone that leaves any kind of company will tell you how tough it was — that’s why you’re not there anymore,” Ms. Brown said. “I’m a good girl. I don’t live my life trying to piss people off, but honestly sometimes I can’t help it.”
After leaving her namesake company behind in 2016, Ms. Brown cycled through relief, anger and sadness. “I thought I was going to spend weeks and days in bed,” she said. “I didn’t. I moped around for a couple days and drank tequila with my best friends.”
In the Bahamas with Mr. Plofker for his 60th birthday, she met a chef who said, “I can’t wait to see what you do next.” “I don’t know,” Ms. Brown said.
“Dude, you got this!” the chef said admiringly.
“And that’s why I’ve got posters and pencils and hats that say, ‘I got this,’” Ms. Brown said. “It just kind of clicked.”
What Do Millennials Want?
Not all of her experiments have worked out. A stint as editor of Yahoo Beauty ended after two years. (“Like going to grad school,” Ms. Brown said.) A consultancy at Lord & Taylor, with justBOBBI boutiques selling products from other lines as well as her own, has quietly ended. “We just didn’t have the manpower,” she said. “It was a great creative project, but we’re overwhelmed and something had to give.”
It was time for lunch. Ms. Brown ordered a Bobbi salad, whose christening raised $10,000 for a school fund-raiser, from the renowned local sandwich shop Egan & Sons: avocado, string beans, white and black beans, bell peppers, red onion, chopped romaine, cilantro and lemon vinaigrette. Plus anchovies on the side.
She had gone to bed at 9:30 the previous evening after returning again from the Bahamas, splashing her face with water (of makeup, she said, “I don’t really wear any”) and applying a new soothing cream derived from hemp oil on her neck and feet. The name escaped her.
“Theramu!” her team said in chorus.
“I think I took too much of it last night, I’m a little tired this morning,” Ms. Brown said. “I was supposed to do a half a dropper but didn’t measure. THC is marijuana to get you high. This is the CBD part, this is legal, and I think it’s going to be the biggest trend. It’s amazing, I’ve been putting some on Biggie, she has a little boo-boo on her tail.”
An employee, Tara Tersigni, mentioned that Ms. Brown just met with Jen Atkin, a hairstylist and social-media influencer with her own line. “She kind of came up with the Kardashians, did their hair and still does all the ‘It’ girls,” Ms. Tersigni said. “And she said to Bobbi, ‘You’re the O.G.” Pause. “Original gangster.”
“Then she said I’m ‘cool AF’ and I’m like, what the hell is ‘AF’?” Ms. Brown said.
How are millennial women, who have embraced pared-down makeup lines like Emily Weiss’s Glossier, different from her generation?
“I think they are much cooler, much more simple and caring about things that matter, meaning family, work,” Ms. Brown said. “I think it’s not about the big giant handbag, not about the designer. It’s not about a cream that promises you endless possibilities. Honestly, I think that the young girls are more simple and they just want the truth. They don’t want, like, marketing-speak. They don’t want gobbledygook.”
The “Satisfaction” riff sounded; Ms. Brown let the call go to voice mail. She recalled early in her career, doing a shoot with the photographer Annie Leibovitz. She shut the dressing room door. Then a stylist reopened it. “As I’m cleaning up, I look in the mirror and I’m with the Rolling Stones in their underwear,” Ms. Brown said. “All of them!”
Years later she became friends with a girlfriend of Mr. Jagger, the fashion designer L’Wren Scott who had asked her and the hairdresser Sam McKnight to work on one of her last fashion shows in London. (Ms. Scott committed suicide in 2014.) “She was so kind to me,” Ms. Brown said. “Once she invited me to this amazing dinner with Mick and Ron Wood and Daphne Guinness. One by one all these people would show up. Bryan Ferry.”
The next season, she and Mr. Plofker were invited to a dinner party at Mr. Jagger’s house. “I’ll never forget, we were wondering what are we going to bring them for a gift — what do you give Mick Jagger?” Ms. Brown said. “So Steven bought him a bottle of wine and a Coravin. They said to come at 7 so we came at 7, rang the doorbell. It was only Mick, home alone. L’Wren had to run out for something, and they showed us up to the study — ‘Oh, Bobbi, Steven! How are you?’ And I’ll never forget, he’s like, ‘Oh my God! I can’t believe you bought me a bottle, it’s amazing!’ He loved the Coravin and we sat there like a half-hour, talking with Mick. So there have been so many of those kind of cool situations in my life because of makeup.”
Another happened when the musician Patti Scialfa hired Ms. Brown to do her makeup for the 12/12 concert to raise money for Hurricane Sandy. Ms. Brown told Ms. Scialfa’s husband, Bruce Springsteen, that the first time she came to New Jersey she slept in the Livingston Mall to get tickets to see him, and sat in the last row.
“And here I was in his S.U.V. driving to New York for the 12/12 concert,” she said. “I’m with Patti and Bruce and their daughter who is a doll, and the phone rings and I hear Bruce on the phone saying, ‘Bobby, no, oh Bobby that’s too bad. Oh Bobby, Bobby’ whatever. He hangs up and he says to Patti, you know, ‘Bobby was going to surprise but he couldn’t come.’ Patti looks at me and she said, ‘That’s Bob Dylan.’ So I’m in the Lincoln Tunnel with Bruce Springsteen talking to Bob Dylan. It was bizarre. Yeah, it was one of those moments.”
Finished with her salad, Ms. Brown ate a piece of dark chocolate, which, she said, “kind of closes the deal.” She said she is not concerned about whether the new projects work out. She might do a museum, a “confidence center — you know, empowerment,” write a 10th book, though not a business one, despite that she’s been approached. “I know the title: ‘Duh.’ D-U-H. I have no advice except follow your gut, just be open.”
Buffing Up the Bidens
Ms. Brown was going to do Michelle Obama’s makeup for the 2009 inauguration, but it fell through.
“You know, she went with someone else,” she said. “I was so bummed and someone said, ‘Oh I know someone who knows the Bidens. I was hired to do Mrs. Biden’s makeup, which was awesome. It was an amazing experience. I did Jill’s makeup and touched the vice president up and I found myself alone with him in a hotel room, just me and him with a ruffled bed. I have a picture of it. The door was left open.”
The former second couple now visit Ms. Brown’s beach house on the Jersey Shore, she said. “Joe Biden is the most simple, by-the-book guy. He’s amazing.”
It was the next afternoon, and Ms. Brown, surprisingly fresh considering she’d made a quick trip to Syracuse the previous evening to watch a basketball game and feed barbecue to her youngest son and 60 of his fraternity brothers, was alone in the living room of her penthouse pied-à-terre, in Chelsea, overlooking the Highline, with spectacular views of uptown, downtown, the Hudson River and New Jersey.
She was wearing the same casual attire as the day before. “Even at the White House I wear jeans,” she said. “I don’t go to the White House anymore. I’ll just say that.”
Ms. Brown was, however, scheduled to give a talk about anti-counterfeiting at the United States Chamber of Commerce (which happened this week). “When they first called, I thought they made a mistake,” Ms. Brown said. “But they said, ‘No, we really want you,’ a female entrepreneur that had a global business.”
At the Obamas’ last state dinner, she and Mr. Plofker were in line when former President Barack Obama got her attention. “And I run over and I say, ‘Hey!’ And I said, ‘Oh my God, your skin looks so good! Can I touch it?’” He said yes. “He had quit smoking, I think, at the time. And he’s like, ‘Michelle! B. Brown just told me my skin looks good!’ And Michelle goes, ‘Steven!’ So we had a moment.’”
She hesitated to call Mr. Obama her friend. “But when I would walk into the White House, the president of the United States would say, ‘Hey B squared, how you doing? Nice kicks,’” Ms. Brown said. Mr. Obama eventually appointed her to serve on the United States Trade Commission.
“Even when that happens in my life, my husband says, ‘That’s really dumb, you hate going to meetings,’” she said. “And I said, ‘I know but it’s so cool.’”
And the truth is, those particular meetings weren’t so bad. “I’d be sitting next to someone, the head of the pork bellies,” Ms. Brown said.
Her maternal grandfather, “Papa Sam,” had owned Sandra Motors, a big car dealership in Chicago named after Ms. Brown’s mother. Calling himself “Cadillac Sam,” he appeared in local TV commercials. “And every time I was in these situations I would look up at Papa Sam,” Ms. Brown said, “and think, ‘I used to sit in these corporate meetings, and now I’m here at the White House?’”
In the apartment, staring down at her, was a large portrait of Queen Elizabeth II.
“I mean, look, I haven’t met the queen,” Ms. Brown said. “But I did get a private tour of Buckingham Palace because I had breakfast with her granddaughter Eugenie. I started asking her questions: ‘Eugenie, so your grandma’s the queen?’ Because Eugenie’s this nice sweet girl, Fergie and Andy’s daughter. I’ve had breakfast with Kate Middleton — not Kate, Pippa! Wrong Middleton. But Kate wore Bobbi makeup on her wedding. So all those moments are close though I haven’t met the queen. Yet.”