 Cherryman began his film career appearing in the 1919 comedic film "In For Thirty Days" as Count Dronsky, opposite popular leading lady of the silent film era, May Allison.The following year, Cherryman was chosen by the notable screen diva Alla Nazimova to appear opposite her as Thorne, in her penned dramatic film "Madame Peacock".Cherryman and Nazimova developed a friendship and at Nazimova's request, he was cast in the role Gaston Rieux in the 1921 film that would possibly become his most recalled performance - 1921's Metro Pictures Corporation film adaptation of the Alexandre Dumas, fils novel "La Dame aux Camélias", retitled as "Camille".