The Trouble with Angels is a 1966 comedy film about the adventures of two girls in an all-girls Catholic school run by nuns. The film was directed by Ida Lupino and stars Hayley Mills (in her first post-Disney film role), Rosalind Russell and June Harding.
The film's cast also includes Marge Redmond (who would play a nun in the television series The Flying Nun, which premiered the following year) as math teacher Sister Liguori, Mary Wickes (who later played a nun in the movie 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 had played a nun in The Sound of Music the previous year).
A sequel, Where Angels Go, Trouble Follows, was released in 1968.
The movie is set at St. Francis Academy (also the name of the school in Sister Act 2), a fictional all-girls Catholic boarding school in Pennsylvania, operated by an order of nuns. Rosalind Russell plays the Mother Superior, who spends the movie at odds with Mary Clancy (Hayley Mills), a rebellious teenager, and her friend Rachel Devry (June Harding). The episodic storyline follows the young women through their sophomore, junior and senior high-school years as they pull pranks on the sisters and repeatedly get in trouble. After spending much of the film resenting the authority of the Mother Superior, Mary receives the "call" senior year and, after graduation, remains at the school in the novitiate of the order.
The Trouble with Angels was based on the book Life with Mother Superior by Jane Trahey, about her own high school years at a Catholic school near Chicago, Illinois in the 1930s. While in the novel the school was portrayed as a boarding school outside the city, Trahey attended what is now Providence-St. Mel's High School, which was a day school. Many of the incidents mentioned in the book were based on Trahey's experiences at Mundelein College in Chicago. The character of Mary Clancy (Mills) was based on Jane's friend, Mary, who later became Sister John Eudes, a Sinsinawa Dominican nun.
The Trouble with Angels was filmed in August and September 1965. The St. Francis Academy in the film was filmed on location at St. Mary's Home for Children in Ambler, Pennsylvania. All interior shots were filmed at Columbia Studios at Sunset & Gower in Hollywood. Most exterior shots were filmed at the Greystone Mansion, which was leased by the City of Beverly Hills to the American Film Institute. The exterior train depot scenes at the opening and closing of the movie were shot at an abandoned rail station (which still exists) in Monrovia, California. 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.
The Trouble with Angels enjoyed 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, a new 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".
Burlesque performer Gypsy Rose Lee appears in a small role.
An uncredited Jim Hutton appears briefly as the principal of a competing school.