'Stupid Mistakes': '60s Icon Hayley Mills Struggled To Grow Up In Hollywood

Hayley Mills had a legendary Disney run and starred in films like "The Parent Trap" and "Pollyanna," directly under the tutelage of Walt Disney himself. In addition to helping Hayley carve out a name separate from her famous parents — actor John Mills and novelist Mary Hayley Bell — working with Disney gave her a good foundation in the industry. However, she still struggled to transition into more adult roles and shed her child star image. 

During a May 2026 interview on "The Rosebud Podcast," Hayley admitted that, although Walt had graciously offered to extend her contract after it expired in 1965, she was another star eager to leave Disney behind and try something new. But taking that next step and leaving her child star image behind wasn't easy. "I didn't know who I was," she explained. Mills had trouble establishing herself as an adult in Hollywood because of the public's expectations of her. "There was a part of me that didn't want to disappoint people that, 'Oh, she's not that cute little girl anymore, she's what?'" Mills revealed. Unfortunately, the identity crisis led to career choices that left her with regrets. "I made some crashingly stupid mistakes," she said.

Before actor Sue Lyon took on the starring role in the film "Lolita," Hayley Mills was considered for the part. Even as a young girl, Mills recognized the movie would be an amazing opportunity to help her branch out as an actor. "That would've given me a chance to work with Stanley Kubrick, James Mason, and Shelley Winters and play that marvelous part," she told Yahoo! in 2021. Sadly, the decision to take on the role wasn't up to Mills. Her parents objected to the sexual nature of the film, and as she was still under contract with Disney, the studio didn't want the role to negatively impact their brand. "This was a nymphet and a nymphet really didn't gel with the Disney image," she said.

Though Mills isn't bitter on the same level as other child actors that put Disney on blast, she still thinks about how the role might have impacted the next stretch of her career. "Lolita was the 'role that got away.' That was the one that hurt the most," she wrote in an essay for Literary Hub. "I've always wondered how things might have gone if I had taken such a radically different path." Mills wasn't one of the Disney stars who crashed and burned, and she continued working in Hollywood. But it's still hard to let go of what might have been.