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He enlisted at Chase City, Virginia in the U.S. Army during World War I. Earle Gregory received the Medal of Honor for actions as a U.S. Army sergeant during the Meuse-Argonne Offensive in World War I. He is considered to be the first Virginian to receive the medal and often called the Sergeant York of Virginia.
In 1939, Tobias signed with Warner Brothers and was cast in supporting roles, many times along with James Cagney, in such movies as Cagney's Yankee Doodle Dandy (1942) as well as with Gary Cooper in Sergeant York (1941) and Irving Berlin, Ronald Reagan, and George Murphy in This Is The Army (1943).