Claire Windsor's film debut was in the 1920 release of Lois Weber's "To Please One Woman" which was only a modest success. To promote the nascent starlet, Paramount Pictures often paired Windsor with the newly divorced actor Charlie Chaplin in publicity photographs, leading the tabloid press to give mention to the young actress in print. In 1921, Windsor costarred with Louis Calhern in Weber's "The Blot" (1921). The publicity paid off; in 1922 the newly formed Western Association of Motion Picture Advertisers (WAMPAS) began their annual WAMPAS Baby Stars awards and she was named, along with Bessie Love, Lila Lee, Mary Philbin and Colleen Moore, as the year's most promising starlets. That same year Claire signed a contract with Goldwyn Pictures Corporation. She would appear in "Broken Chains" with fellow WAMPAS Baby Star Colleen Moore.