Barbara Hunter as Marvel-Ann Bernadette Withers as Valerie Vicky Albright as Charlotte Patty Gerrity as Sheila Vicki Draves as Kate Wendy Winkelman as Sandy Jewel Jaffe as Ginnie-Lou Gail Liddle as Priscilla Michael-Marie as Ruth Betty Jane Royale as Gladys Ronne Troup as Helen Catherine Wyles as Brigette The Outsiders: Gypsy Rose Lee as Mrs. Mabel Dowling Phipps Jim Boles as Mr. Gottschalk Kent Smith as Uncle George Pat McCaffrie as Mr. Devery Harry Harvey, Sr. as Mr. Grisson Mary Young as Mrs. Eldridge Jim Hutton as Mr. Petrie (uncredited) Life with Mother Superior The Trouble with Angels was based on the 1962 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 memoir 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 (1922–2017). The Washington Post called it "wonderful fun". The book became a best seller. Production Development In June 1962, the film rights were purchased by Ken Donnellon and Jacqueline Babbin who knew Trahey in advertising. Donnellon said he wanted the film to be seen through the eyes of one of the young nuns. They were unable to make the film. In August 1963 Ross Hunter was pursuing the novel; he wanted Loretta Young, Jane Wyman, Barbara Stanwyck and Virginia Grey to play nuns and Patty Duke and Mary Badham to play students. In September 1964, the film rights were acquired by Columbia Pictures. The film was assigned to producer William Frye who had a multi-picture deal with the studio. Greta Garbo, Frye's original choice for the role of the Mother Superior, rejected the producer's offer of $1 million to star in the film. In November 1964, Frye approached Hayley Mills to appear and she eventually signed on the following May. The role of the Mother Superior went to Rosalind Russell, who said: "I have been around nuns my whole life and I wanted to do justice with them". Frye hired Ida Lupino to direct; at the time Lupino was mostly working on action and