Montgomery was born in
Sikeston, Missouri, on May 27, 1912 to Grover Cleveland Montgomery (1885–1934) and Mary Emily McCord (1885–1962). As a young girl she was in a group of traveling
vaudeville players of the Junior Times Club in
Los Angeles, California. Accompanied by truckloads of ice cream, Montgomery and the others entertained children at hospitals. In May 1924 she performed as an "eccentric" dancer at the
Orthopedic and Children's Hospital in Los Angeles. In 1925 Montgomery entered the
Mary Pickford silhouette contest which selected a lookalike of America's sweetheart. Other aspiring young actresses like
Virginia Davis,
Cecilia Parker, and Mary Kestner, also submitted photos. As a seventeen-year-old
Hollywood High School student, Montgomery acted the part of a maid in the stage play
Bad Babies. An attorney for the California State Department of
Industrial Relations ruled that the theme of the production was too risque for a minor actress to appear in. Montgomery was required to wait until her eighteenth birthday in 1930 to participate. She became upset over the ruling. Her mother, Mary Cleveland, hired a private tutor so that Montgomery would comply with the Los Angeles compulsory school laws. An
understudy, Dorothy Gould, took over the role. Montgomery's career as a film actress was quite brief. She had an uncredited role as a student in
Freshman Year (1938). ==Career as a fashion designer==