Theater
The Siasconset colony was evenly divided among actors and artists, and painters often gave theatrical performances.
Kennedy appeared in a skit written by Kenneth and Roy Webb and impressed professional Harry Woodruff, who commented, "She could act rings around anybody." As a result, she was offered the lead opposite Woodruff in The Genius. Soon she was in Cleveland, where Robert McLaughlin gave her work with his stock company.
Kennedy first appeared on Broadway in Little Miss Brown (1912), a farce in three acts presented at the 48th Street Theater. Critics found Kennedy's performance most pleasing, writing, "Miss Kennedy's youth, good looks, and marked sense of fun helped her to make a decidedly favorable impression last night." That same year she appeared in The Point of View.
1914 saw her in the popular Twin Beds, and in 1915 she scored a sensational hit at the Eltinge Theater as Blanny Wheeler opposite John Cumberland in Avery Hopwood's classic farce, Fair and Warmer, which ran 377 performances. Critic Louis Vincent DeFoe wrote, "Madge Kennedy proves anew that consummate art is involved even in farcical acting." In the late Teens she would leave the stage for three years to appear in moving pictures for Samuel Goldwyn (see "Films" below).
Kennedy returned to the New York stage in November 1920, playing in Cornered, staged at the Astor Theatre. Produced by Henry Savage, the play, taken from the writing of Dodson Mitchell, offered Kennedy a dual role.
In 1923, she starred opposite W.C. Fields in Poppy, where she enjoyed top billing. In the comedy, Beware of Widows (1925), which was produced at Maxine Elliott Theatre, a reviewer for The New York Times noted, once again, Kennedy's physical beauty as well as her skill as a comedian.
Later, she starred in Philip Barry's Paris Bound (1927) and in Noël Coward's Private Lives (1931), having succeeded Gertrude Lawrence.
After an absence of 33 years, she returned to Broadway in August 1965, appearing with her good friend Ruth Gordon in Gordon and Kanin's A Very Rich Woman.