Naldi was asked to perform in a short film with Johnny Dooley, a Scottish comedian who, despite his last name, was unrelated to her. She soon quit the film, however, after realizing that Dooley had romantic intentions with another woman. Naldi was then offered a role in "A Divorce of Convenience" with Owen Moore. Following those two films, she had small roles in several independent films before being cast as the exotic character Gina in Paramount Pictures's 1920 release" Dr. Jekyll and Mr. Hyde" starring John Barrymore. Barrymore himself reportedly recommended her for the role after he “spotted” her dancing at the Winter Garden. Her noted performance in that film subsequently afforded Naldi more career opportunities. It also established her long-term friendship with Barrymore, who affectionately nicknamed her his “Dumb Duse”.