Brooke Shields Dishes Trump and Madonna in a New Cabaret Show

“Most of the time, I’m halfway content.”

Those words are Bob Dylan’s, and they were delivered one night last week by Brooke Shields during her sold-out debut show at the Café Carlyle, the intimate Manhattan supper club where Bobby Short, Elaine Stritch and Debbie Harry have performed.

It was five months after Ms. Shields had returned to the spotlight with “Pretty Baby: Brooke Shields,” an acclaimed documentary that chronicled the ups and downs of a career that got its start in the 1970s, when she was a child model and actress marketed as a sex symbol.

A number of celebrities came out to see her at the venue, which is blocks away from the Upper East Side apartment where she grew up. At a table close to the stage were the actors Naomi Watts, Billy Crudup and Laura Dern. Nearby sat Mariska Hargitay, with whom Ms. Shields has worked with on “Law & Order: SVU.” The crowd also included two men who had done cabaret at the Carlyle: Isaac Mizrahi, who designed the loosefitting orange dress Ms. Shields was wearing, and Alan Cumming.

Whether by design or chance, Ms. Shields, 58, has reflected the mood of the times across her nearly five-decade career. In the louche, druggie ’70s, she starred (at age 11) in “Pretty Baby,” the Louis Malle film about a romantic relationship between an adult man and a child prostitute. In the striving, just-say-no ’80s, she graduated from Princeton and wrote a self-help book for teenagers in which she discussed her decision to remain a virgin.

The celebrity guests at the show included, from left, Laura Dern, Billy Crudup and Naomi Watts.Credit…Tony Cenicola/The New York Times

In the next decade she starred on Broadway (in a revival of “Grease”), displayed a talent for pratfalls in a hit sitcom (“Suddenly Susan”), and married and divorced a tennis star (Andre Agassi). In 2001, she married the comedy writer and filmmaker Chris Henchy, with whom she has had two children, and returned to the Broadway stage in “Chicago.” She has also found time to write memoirs and host a podcast, “Now What.”

And Ms. Shields pointed out during the show that somewhere along the course of her varied career: “I performed at Sea World. With Lucille Ball.”

Her Café Carlyle residency is scheduled to run through Sept. 23. Every night is sold out. On Tuesday, she opened with “I Think We’re Alone Now,” making it into an ironic lament about how she has rarely felt alone since her mother decided she would be a star.

“I practically came out of the womb famous,” she said, during a spoken-word interlude. “They tell me the doctor asked for a selfie.”

She also went through periods when career seemed to be over: “The other day,” she said from the stage, “I was in the airport and the flight attendant came up to me and said, ‘Oh my God, you’re Caitlyn Jenner!’”

In “Fame Is Weird,” a song written for the show by Matthew Sklar and Amanda Green, she moved from her encounters with the public to her experiences with fellow celebrities. In the intro, she said she had turned down Donald J. Trump when he asked her out on a date, but soon conceded that she had consented to Elizabeth Taylor’s request that she pre-chew her gum.

“I chewed it first,” Ms. Shields said, “so I got the better end of the deal.”

Mariska Hargitay, seen here speaking with the actor Beth Ostrosky Stern, worked with Ms. Shields on the show “Law & Order: SVU.” Credit…Tony Cenicola/The New York Times

She also recounted being mean girl-ed by some of he world’s best-known women. When she met Bette Davis at the Oscars, she said, “Hi, I’m Brooke Shields,” to which the star replied, “Yes, you are.” A similar encounter occurred when Ben Stiller brought her to Madonna’s house, Ms. Shields said. The greeting she received from Madonna was curt: “Oh, you.”

In many ways, the show seemed like an effort by Ms. Shields to work through her ambivalence about having fallen closer to earth after the years of childhood and teenage stardom. In the second half, she roasted and paid tribute to her mother, Teri Shields, who in the ’70s and ’80s became a focal point for the culture’s misgivings about stage parenting and the sexualization of children in Hollywood.

“She has been in the press almost more than I have,” Ms. Shields said, “and, probably, you all have your opinions of her.”

She went on to note that life with her mother, who died in 2012, wasn’t all bad.

“There was a lot of laughter and so much fun,” she said. “She would do really crazy things. She would see a dog tied outside of a store, waiting for their owner to come back, and she would get right down in front of the dog to say, ‘They’re never coming back.’ It was just so sick. It’s dark. But really funny.”

She also acknowledged her mother’s alcoholism. “We named a cocktail at the bar for her. Actually, we named several for her,” Ms. Shields said, before getting serious about how much she missed her. She added that one reason she wanted to play the Carlyle was that it was a place her mother had taken her when she was young. “She would be really proud,” she said.

With that, she launched into Mr. Dylan’s melancholy “Most of the Time.”

Ms. Shields donned a cowboy hat to sing the Dolly Parton hit “9 to 5.”Credit…Tony Cenicola/The New York Times

Ms. Shields, who appeared to have a cold, sounded a bit like Bob Dylan as her throat began to give out. She then moved into material about the trials and tribulations of being a wife tot Mr. Henchy, who was seated in the audience, and the mother of two teenage daughters, Rowan and Grier. While delivering Tina Dico’s “Count to Ten,” she apologized to a man seated close to the stage, who was catching much of her spit.

Toward the end, she sang “Faith,” a 1987 hit by someone she knew, George Michael. She delivered the lyrics with conviction while also using the song to make a cheeky reference to the nights when she stepped out before the paparazzi in the role of the public girlfriend to Mr. Michael and Michael Jackson.

After the applause, the fashion designer Christian Siriano offered a quick review: “She was great, even though she clearly has Covid.”

Moments later, Ms. Shields emerged from her dressing room and went through some quick hellos with friends and well-wishers. A waiter asked her what she would like to drink. “Tequila,” she said, before moving to a corner table for a chat with a reporter.

Told of Mr. Siriano’s thoughts, she said, “I don’t have Covid!” But she said she did have a respiratory ailment that had landed her in the hospital a few days before the show.

Her vocal coach brought her cough drops. Publicists hovered. Ms. Shields explained that her cabaret show began taking shape in the spring. Working with the writer and director Nate Patten, as well as with the musical director Charlie Alterman, she said she wanted to put together an evening that would involve telling her own story truthfully while making it a source of comedy.

Alan Cumming in the company of Ms. Dern.Credit…Tony Cenicola/The New York Times

She was aware that this was a difficult moment to humanize the people who decided it was appropriate for her to appear in a movie at age 11 as someone whose virginity was auctioned off. Yet her mother was still her mother, and she loved her.

“Ambivalence is where real life happens,” she said. “I mean, the point of it all is that we’re not one thing or the other. We’re human beings, and we’re fraught.”

Ms. Shields was asked about her experience with Mr. Trump.

“I was making some movie in the late-90s,” she said. “My phone rang and it was him. He said, ‘You and I should date. You’re America’s sweetheart, and I’m the world’s richest man. People will love it.’ At which point I stifled laughter and said, ‘Thank you, I’m very flattered, but I have a boyfriend and I don’t think he would appreciate me stepping out on him.’ And he said, ‘Well, I think you’re making a big mistake.’ I said, ‘Well, I’m going to have to take my chances.’”

Did she not know that George Michael was gay? And did they really go on a date?

“A few,” she said. “He was very respectful of my virginity.”

“Read the book!” a publicist yelled, referring to “There Was a Little Girl,” the 2014 memoir in which she tells the tale.

Ms. Shields added that, despite the appearance that her relationships with Mr. Michael and Mr. Jackson seemed merely for show, she had real bonds with both of them.

“We had so much fun,” she said. “I wasn’t just a purpose, as a beard. It actually was more than that. The conversations, the fears, the discussions.”

The talk turned to her podcast — in which she has spoken with Stacey Abrams, Rosie O’Donnell, Chelsea Handler and Kris Jenner — and the one person she has been itching to get: Britney Spears, who hasn’t given in an interview in years.

“I tried very hard to find a way to be the first actual interview,” Ms. Shields said. “And I haven’t gotten it. But I am the only person who could do justice to the reality of the story. Whatever it is.”

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