Hayley Mills was already a global superstar when she stepped onto the set of St. Francis Academy. You probably remember her from The Parent Trap or Pollyanna, but there was something different about 1966. She was twenty. She was trying to shed that "Disney girl" image without completely alienating the families who adored her. Honestly, she nailed it. The cast of The Trouble with Angels didn't just capture a moment in 1960s cinema; they created a blueprint for every "rebellious teen in a strict school" movie that followed.
It’s a coming-of-age story that actually feels like it’s aging with us.
The Powerhouse Duo: Hayley Mills and June Harding
The movie lives and dies on the chemistry between Mary Clancy and Rachel Devery. If you haven't seen it in a while, you might forget how genuinely funny June Harding was. While Hayley brought the name recognition, June brought this jittery, frantic energy that balanced Mary’s cool-headed mischief.
They were "Scoundrels." That was the word, right?
June Harding didn't have the massive film career Hayley did, which is a shame. She mostly stuck to television and stage work after this, appearing in things like The Richard Boone Show. But in this specific 112-minute window of time, she was the perfect foil. When they’re smoking cigars in the boiler room—the infamous "Secret Service" headquarters—you believe they’re best friends. You believe they’re actually terrified of getting caught.
Rosalind Russell: More Than Just a Mother Superior
We have to talk about Rosalind Russell. If you’re a classic film buff, you know her as the fast-talking reporter in His Girl Friday. By the time she joined the cast of The Trouble with Angels, she was Hollywood royalty. She could have phoned this in. A lot of actors playing nuns in the 60s did. They were either "singing nuns" or "scary nuns."
Russell did something else.
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She gave the Mother Superior a dry, acerbic wit that masked a deep, aching empathy. There’s a specific scene—one that usually makes people cry even on the fifth rewatch—where she’s polishing the chapel floor alone. No dialogue. Just her working. It’s the moment Mary Clancy realizes that being a nun isn't about hiding from the world; it's about serving it. Russell’s performance is the spine of the movie. Without her gravitas, the pranks would just feel like a shallow sitcom.
A Who’s Who of Character Actors
The supporting cast is where the movie gets its texture. You’ve got Binnie Barnes as Sister Celestine. Fun fact: Binnie Barnes was actually married to the film’s producer, Mike Frankovich. She had this incredible, regal presence. Then there’s Mary Wickes as Sister Clarice.
Mary Wickes is a legend.
If she looks familiar, it’s because she basically played the same "tough but lovable" nun nearly 30 years later in Sister Act. She had a way of using her height and her voice to command a room without ever raising her volume.
The rest of the girls in the school weren't just background extras. You had:
- Camilla Sparv as the beautiful Sister Angela (who Mary thinks is too pretty to be a nun).
- Barbara Hunter as Marvel-Ann, the perpetual victim of Mary and Rachel’s schemes.
- Portia Nelson as Sister Elizabeth. Portia was actually a cabaret singer and a songwriter in real life.
It’s a dense cast. Every time the camera pans across a classroom, you’re looking at women who were either Broadway veterans or rising starlets. It felt like a real community because, behind the scenes, Ida Lupino made sure it functioned like one.
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The Ida Lupino Factor
You can’t discuss the cast of The Trouble with Angels without discussing the woman behind the camera. Ida Lupino was a trailblazer. She was one of the few women directing in Hollywood at the time, and she had a reputation for being "tough as nails."
She understood these girls.
Lupino didn't want a "saccharine" movie. She pushed for the grit. When the girls are putting bubble bath in the sisters' sugar bowls or crashing the tour of the girls' school, Lupino directed it with the timing of a heist movie. She treated the teenage rebellion with respect rather than condescension. That’s why the movie doesn't feel as dated as other 1966 releases. The clothes changed, sure, but the feeling of being seventeen and trapped in a system you don't understand? That’s universal.
What Happened to the Rest of the Students?
People always ask about the other girls. Barbara Hunter, who played Marvel-Ann, did a few more things (like The Virginian) but eventually drifted away from the spotlight.
The "trouble" wasn't just on screen.
The production was notoriously fun. Working with dozens of young women on a closed set created a sorority atmosphere. Many of the younger cast members mentioned in later interviews that Rosalind Russell acted like a mentor to everyone, not just Hayley Mills. She was the "Mother Superior" on and off the clock, ensuring the young actresses stayed professional while still enjoying the chaos of a big-budget production.
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Why the Sequel Didn’t Quite Hit the Same
A few years later, they made Where Angels Go, Trouble Follows. Stella Stevens took over the "young nun" role, and Rosalind Russell returned. But Hayley Mills and June Harding were gone.
It felt empty.
The magic of the original cast of The Trouble with Angels was the specific chemistry between the two leads. You can’t just swap out Mary Clancy. The first film ends on such a poignant, perfect note—Mary staying behind to join the order while Rachel leaves on the train—that a sequel almost felt like it was betraying that goodbye. The original film is about a very specific transition from childhood to adulthood. Once that bridge is crossed, you can't really go back.
Exploring the Legacy
If you're looking to dive deeper into this era of film, there are a few things you should actually do. First, go back and watch Rosalind Russell in Auntie Mame. It’ll blow your mind to see her play such a flamboyant character right next to her restrained performance as the Mother Superior. It shows her range in a way that modern audiences often miss.
Second, check out Hayley Mills in The Chalk Garden. It was made around the same time and deals with much darker themes of adolescence. It’s the perfect "double feature" if you want to see how she was evolving as an actress during the mid-60s.
Finally, track down a copy of the original book by Jane Trahey, Life with Mother Superior. It’s based on her real experiences at a Catholic boarding school. Seeing how the cast of The Trouble with Angels brought those real-life people to the screen adds a whole new layer of appreciation for their work.
The movie works because it isn't cynical. It acknowledges that life is a series of "troubles," but if you have the right people around you—even if they're nuns in habits—you'll probably turn out just fine.
To truly appreciate the film's impact today, watch it with someone who hasn't seen it. Notice how they react to the ending. It's one of the few "twist" endings in cinema history that isn't a gimmick; it's a character revelation. That’s the power of a perfectly assembled cast.