Grapewin began in silent films at the turn of the twentieth century. His very first films were two "moving image shorts" made by Frederick S. Armitage and released in November 1900; "Chimmie Hicks at the Races" (also known as "Above the Limit") and "Chimmie Hicks and the Rum Omelet", both shot in September and October 1900 and released in November of that year. During his long career, Grapewin appeared in more than one hundred films, including "The Good Earth", "The Petrified Forest", "The Grapes of Wrath", "Tobacco Road", and in what is probably his best-remembered role: Uncle Henry in "The Wizard of Oz". Prior to being cast in that film, Grapewin performed in Metro-Goldwyn-Mayer's "Broadway Melody of 1938" with Judy Garland (Dorothy in "Oz") and Buddy Ebsen (the original Tin Man in "Oz"). He also performed with Garland in "Listen, Darling." Later, in the early 1940s, he had a recurring role as Inspector Queen in the Ellery Queen film series.