'Hannah Montana' turns sweet 16: Brooke Shields recalls daughter's jealousy when she played Miley Cyrus's mom

Miley Cyrus and Brooke Shields co-star in an April 2007 episode of
Miley Cyrus and Brooke Shields co-star in an April 2007 episode of Hannah Montana. (Photo: Joel Warren/Disney Channel/Courtesy: Everett Collection)

Brooke Shields remembers her time on TV's Hannah Montana, on which she played the late mother of Miley Cyrus's character, teen Miley Stewart and her secret alter ago, pop star Hannah Montana, oh-so fondly. She's especially complimentary of Cyrus.

"Miley was so, so lovely to my daughter, because my daughter had never seen me, you know, hug another girl and call another person my baby girl," Shields tells Yahoo Entertainment. "I had to do that, so she was like, 'No, she's my mama!' And Miley was like, 'We're just pretending. Thank you for letting us borrow your mom for the day.'"

(Cyrus's real-life dad, Billy Ray Cyrus, played Miley's father.)

When Shields first appeared on the Disney favorite in 2007, her own daughter Rowan — the first of two girls she shares with her husband, TV writer and producer Chris Henchy — was still a toddler. In August, Shields took Rowan to college. So, yes, Hannah Montana, which first aired this week on March 24, 2006, has been a part of pop culture for 16 years now. Fans are still there for the show, which continues to air in reruns and fuel demand for merchandise, from T-shirts and hoodies to backpacks and keychains, and so are the people who starred in it.

Miley Cyrus greets
Miley Cyrus greets Hannah Montana fans at Epcot on April 26, 2007. (Photo: Gerardo Mora/Getty Images)

As Shields recalls, by the time she stepped on set in the show's second of four seasons, she already knew the showrunners and most of the crew members. They had worked on her NBC sitcom Suddenly Susan, which had ended its six-season run in 2000. And the experience only got better.

"You come into a show that's really up and running for years, and it’s a well oiled machine, [but] they just, they made me an integral part immediately," Shields says, "and that couldn't have been sweeter."

'Simply put, Miley is the best'

Actor Jason Earles played another of Miley Stewart's family members, her big brother, Jackson, on all 100 episodes and in the 2009 movie. He has equally fond memories of making it.

"Simply put, Miley is the best. I was always blown away with her comedic instincts and her musical talent," he tells Yahoo Entertainment. "My favorite thing about her was I always knew where I stood with her! She was blunt and honest. I knew she had my back on the show and in real life too. I couldn't have asked for a better little sister."

Jason Earles, left, stars alongside Miley Cyrus and her dad Billy Ray on a fourth season episode of
Jason Earles, left, stars alongside Miley Cyrus and her dad Billy Ray on a fourth season episode of Hannah Montana. (Photo: Craig Sjodin/Disney Channel/Courtesy Everett Collection)

However, it almost didn't happen. Earles, who followed in the TV tradition of playing a teenager when he was in his 20s as the show began, recounts that he almost didn't audition for the part.

"Jackson was originally supposed to be super introverted and talk to people using an orangutan hand puppet named Fletcher," Earles says. "I just couldn't imagine spending years of my life doing puppet jokes."

But he went anyway, only to have his hopes dashed — at least at first.

"I mostly remember going to Disney for the final call back and seeing the other kid who was also reading for the role," he says. "He had an amazing hand puppet that looked completely custom built. I had a sock that I drew two eyes on. I thought for sure the other kid would get the role, just based on how awesome his puppet was compared to mine!"

After Earles — and his lackluster hand puppet — won the job, he was relieved when the puppet storyline died.

"During rehearsal, there was only one scene with Miley, Billy Ray and myself that did not include the puppet," Earles says. "Instead of being introverted in the scene, I was just an obnoxious older brother who was not impressed by his pop star sister. The writers loved the dynamic so much, they decided to scrap the puppet."

'I love you, Hannah Montana'

Cyrus herself paid tribute to the show on its 15th anniversary with a letter, written on pastel stationery and decorated with stars, just the way Hannah would do it.

She noted that a lot had changed since she first put on the Hannah wig.

"I experienced falling in love for the first time in those years," she wrote. "Embarrassingly started my period in a pair of white capris of course on the day a 'cute guy' was cast and asked to have lunch with me. Instead I spent it in the bathroom with my mom sobbing and scrambling to find a pair of fresh denim."

The "Best of Both Worlds" singer explained that she had spent more time with Earles and their other co-stars, including Emily Osment and Mitchell Musso, than with her family, with the exception of her dad, her carpool partner until she got her own car.

"You have all my love and utmost gratitude," she wrote. "Breathing life into you for those six years was an honor."

Her final line was, "I love you, Hannah Montana."

Hannah Montana is available to stream on Disney+.