	Rolph entered the shipping business in 1900, by forming a partnership with George Hind. Over the next decade, he served as president of two banks, one of which he helped establish. Although he was asked to run for mayor in 1909, he chose to wait until 1911 to run for mayor—a position that he would hold for nineteen years. As mayor, he was known as "Sunny Jim" and his theme song was "There Are Smiles That Make You Happy". In 1915 he appeared as himself in an early documentary film titled "Mabel and Fatty Viewing the World's Fair at San Francisco", which was directed by and starred Fatty Arbuckle. In 1924, Rolph appeared as himself in a Slim Summerville comedy short film, "Hello, Frisco."