[1][2] Early successes at the theatre included Never Say Die (1912), Today (1913), The Midnight Girl (1914), Just a Woman (1916), The Man Who Stayed at Home (1918), The Storm (1919), and Opportunity (1920) starring Nita Naldi.

[3][4] On November 11, 1926, the theatre premiered The Squall by Jean Bart, starring Blanche Yurka, Romney Brent, and Dorothy Stickney.

[1] During the final act of the performance July 26, 1927, 38-year-old screenwriter and film executive June Mathis was stricken and died[5] following a heart attack.

[1][2][7] The Windsor, along with the Princess Theatre, was used for Labor Stage, a project of the International Ladies' Garment Workers' Union, which produced plays and held lectures and meetings.

Perhaps the most notable play at the Windsor was a January 3, 1938, revival of Marc Blitzstein's controversial political musical The Cradle Will Rock, produced by Grisman and directed by Orson Welles.