Brooke Shields on Going Out With JFK Jr. Once, Breaking Dean Cain’s Heart Twice, and Parting Ways With Her Mother

Superstar actress and model joins the Stern Show to discuss her eye-opening documentary series, “Pretty Baby: Brooke Shields”

April 4, 2023

To say actress, model, and all-around icon Brooke Shields has lived nearly her entire life in the limelight would be an understatement. At just 11 months old she became the face of Ivory Soap, and her modeling career took off from there. By 14, Shields was covering Vogue magazine. In 1980, when Brooke was still just 16, she starred in a hypersexualized jeans commercial that catapulted her to superstardom and put designer Calvin Klein on the map. Her film career followed a similar trajectory with the young actress starring in the controversial drama “Pretty Baby” — where she played a child prostitute opposite Susan Sarandon — and the equally risqué “Endless Love” and “The Blue Lagoon” before she was old enough to vote. Brooke was far and away the most talked about and sought after child star of her generation, but during her Stern Show debut on Tuesday she told Howard that her fame had come at a price.

“I was never protected by the people that you think would look after somebody,” the 57-year-old superstar told Howard and his listeners.

The candid conversation covered everything from her high-profile upbringing and past celebrity relationships to her two-part documentary series “Pretty Baby: Brooke Shields,” which explores family, stardom, and the true cost of being pushed into becoming a sex symbol at a very young age.

When she was just nine or ten, Brooke’s mom and manager Teri Shields allowed her to participate in a nude photoshoot for the Playboy Press publication Sugar ‘n’ Spice. The pictures were eventually published a few years later even though Shields filed a lawsuit hoping to keep them from seeing the light of day. “I lost, and the prosecuting attorney was just such a prick,” Shields recalled. “He was making lewd gestures to me [in court], and nobody was seeing it.”

Howard couldn’t understand why Brooke’s mom allowed her to take part in a photoshoot like that at such a young age.

“She had this crazy justification for things. She believed that as long as she was in my personal life, keeping me safe and pure and virginal and all that, that she was saving me,” Brooke said, explaining their working relationship ultimately proved untenable, so she abruptly ended it.

“She was sort of raging and couldn’t believe I left her in such a violent way,” Shields told Howard, adding, “She saw the fighter in me. Although she was angry, I think she was [like], ‘Alright, she’s not a wimp, the kid.’”

Making the Dean Cain’s List at Princeton

Photo: Ron Galella Collection via Getty

In 1983, at the height of fame, Brooke put her modeling and movie careers on hold to attend Princeton University. “What a move,” Howard marveled.

“They paired me with like three pre-med students. One of them didn’t even bring sheets … I was like, ‘This is surreal,’” Brooke recalled with a laugh.

As Brooke explained it, being the most famous person on campus wasn’t always easy. She said the university was open to the public, so an undercover security detail followed her to class and kept her safe. “People were trying to bribe students to sneak pictures of me in the shower,” she recalled.

But it was at Princeton where she eventually found her Superman. Well, Dean Cain, the man who famously went on to play TV’s Superman. “We had such a lovely, beautiful courtship,” Brooke told Howard, explaining they dated for a long time before she gave him her virginity. “The guy was the most patient human being on the planet. I don’t know how the hell he did it,” she continued with a laugh. “He was in love.”

Unfortunately, Brooke didn’t prove to be his Lois Lane. “We broke up once because I had only ever been with him in every way. I thought, ‘God, I can’t get married, so I better branch out,’” Shields recalled. “[He was] very angry and very hurt.”

Brooke and Dean gave themselves a second chance at romance sometime later, but again it didn’t work out. “I was just sort of growing away from the older me,” she told Howard. “I was really separating from my mom and really needing to separate from him because he was of a different era in my psyche, you know? And I needed to be challenged differently.”

One and Done With John John

From dating actors like Dean Cain and Liam Neeson to marrying tennis star Andre Agassi, Shields has been no stranger to serious romances with other high-profile celebrities. But with John F. Kennedy Jr., the eldest son of John F. Kennedy and Jackie Onassis, their relationship never progressed beyond the first date.

“I was so madly in love with him since the time I was like three. My mom would say, ‘That’s the boy you’re going to marry,’” Brooke said.

She met John Jr. a few decades later in Aspen, Colorado, where she tried impressing him on the slopes despite having never skied. “I had to get ski lifted out because I went into the trees,” Brooke recalled. “And he didn’t help me, but I was like, ‘It’s okay. He can’t help me. He’s John John.’”

The two hit it off soon thereafter. “He kept saying I look like his mother, which is really interesting, and a compliment, [but] I was like, ‘I don’t know how to feel about this.’ And then we did have a real date.”

Recounting their date, Brooke revealed the night began at a rowdy pub filled with barfights, drinking, and plenty of Kennedys. “He said, ‘Do you want to get out of here?’ And I was like, ‘Uh, yeah, I do want to get out of here, John Kennedy.’”

So, they went back to his hotel. “He kissed me, and it was like the best kiss I’ve ever had in my life,” she continued. “It was beyond not-disappointing. The lips are beautiful, and the face is amazing … and he was down to earth and funny and irreverent.”

Shields called it a night once she felt herself falling for him. “I was so afraid of being really hurt because if I slept with him I would’ve given him my entire universe,” she said, adding, “I had to get a cab home, which was a little less chivalrous.”

Things went from bad to worse the next day on the slopes. “He didn’t look at me and he didn’t talk to me,” Brooke told Howard. “On the one hand, I was like ‘shit!’ On the other hand, I was like, ‘Thank God … He showed his true colors.’”

“Pretty Baby: Brooke Shields” is streaming now on Hulu.