In 1906, Madge went to New York City to study at the Art Students League where she hoped to become an illustrator. This lasted until she appeared in a student musical, which led to a full time job in a traveling stock company. By 1912, Madge was a Broadway Star with the bedroom farce "Little Miss Brown". For the next five years, Madge continued to find success on Broadway appearing in similar roles. Within 3 months of the formation of Goldwyn Pictures, Sam Goldwyn had signed Madge Kennedy to a big movie contract. Goldwyn was at his best when it came to publicity. It was Goldwyn himself who gave Madge the title of "winsome", and Madge was as winsome and sweet as her light comedies suggested. Some of her films were 'Baby Mine (1917)', 'Our Little Wife (1918)', The Kingdom of Youth (1918)' and 'Dollars and Sense (1920)'. While at Goldwyn, Madge shared a dressing room with actress Mabel Normand. After 21 films, Madge left Goldwyn Pictures and appeared in a handful of films produced by her husband, Harold Bolster. These films included 'The Purple Highway (1923)' and 'Bad Company (1925)'. After that, Madge retired from the screen and returned to the stage. After a few years and her remarriage, Madge retired from acting altogether. In 1952, Madge was coaxed out of retirement by George Cukor for the small role of Judge Carroll in 'The Marrying Kind (1952)'. With that, she started another career as Character Actress appearing in films like 'Lust for Life (1956)', 'The Catered Affair (1956)', 'North by Northwest (1959)' and 'The Day of the Locust (1975)'. On the small screen, Madge played the part of Aunt Martha on "Leave It to Beaver (1957)".