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The Trouble with Angels (1966) is a comedy film about the adventures of two girls in an all girls school run by nuns. The movie was directed by Ida Lupino and stars Rosalind Russell and Hayley Mills. The featured players include Marge Redmond (who appeared as nun Sister Jacqueline in the television series The Flying Nun the following year) as math teacher Sister Liguori, Mary Wickes (who also played a nun in Sister Act and its sequel Sister Act 2: Back in the Habit) as gym teacher Sister Clarissa, and Portia Nelson as art teacher Sister Elizabeth (who also played a nun in The Sound of Music).


The movie is set in a fictional all-girls Catholic boarding school operated by an order of nuns. Russell plays the Mother Superior, who spends the movie at odds with Mary Clancy (Hayley Mills), a rebellious teenager, and her misery-loves-company friend Rachel Devery (June Harding). The episodic storyline follows the young women through their high-school years.


The Trouble with Angels was based on the memoir,Life with Mother Superior by Jane Trahey about her own high-school years at a Catholic school near Chicago in the 1930s. While in the novel the school was portrayed as a boarding school outside the city, Trahey actually attended what is now Providence-St. Mel's High School, which was only a day school. Many of the incidents mentioned in the book were actually based on Trahey's experiences at Mundelein Collegemarker in Chicago, Illinoismarker. The character of Mary Clancy (Mills) was based on Jane's actual friend, Mary, who later became Sister John Eudes, a Sinsinawa Dominican nun.


The Trouble with Angels was filmed from September to December 1965. The St. Francis Academy in the film was filmed on location at St. Mary's Home for Children in Ambler, Pennsylvaniamarker. All interior shots were filmed at Columbia Studios at Sunset & Gower in Hollywood. The film was budgeted at $2 million.


The film marked a departure for Mills, who was attempting to emerge from her juvenile leads in Walt Disney-produced teen comedies as a comedic actress. It would be the last successful film of her career, as her next film, The Family Way, would spark controversy in Englandmarker due to a nude scene with Mills. Though the incident was minor, it effectively hurt Mills' blossoming career as a young actress.

The Trouble with Angels enjoyed mediocre to good reviews and enough success to warrant a sequel (Where Angels Go, Trouble Follows). However, Mills opted not to reprise her role as the progressive protagonist and was replaced by Stella Stevens, who played Sister George, foil to Rosalind Russell’s Mother Superior. Variety magazine said "An appealing story idea...hip Mother Superior nun who outfoxes and matures two rebellious students in a Catholic girls' school...has lost impact via repetitious plotting and pacing, plus routine direction".

Uncharacteristically, Russell criticized Mills' professionalism in her memoirs, stating that the young actress was difficult to work with (the only co-star to work with the beloved Mills to publicly gripe). Russell credited her Catholic-school education as inspiration for her role as Mother Superior.


Burlesque performer Gypsy Rose Lee appears in a small role. Previously, Rosalind Russell played Lee's mother in the 1962 film Gypsy.

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