Oakland was born in the Brooklyn borough of New York City, the son of a plasterer and builder Jacob Weiss and his wife Ethel Oaklander. While he later claimed in media interviews to have been born in 1922 (a date repeated in his New York Times obituary), Social Security and death indexes indicate he was born Simon Weiss in 1915; his stage name was likely derived from his mother's maiden name, Oaklander.