Tucker described himself as a farm boy. He was born in Plainfield, Indiana, on February 12, 1919, a son of Forrest A. Tucker and his wife, Doris Heringlake. His mother has been described as an alcoholic. Tucker began his performing career at age 14 at the 1933 Chicago World's Fair, pushing the big wicker tourist chairs by day and singing "Throw Money" at night. After his family moved to Washington, D.C., Tucker attracted the attention of Jimmy Lake, the owner of the Old Gaiety Burlesque Theater, by winning its Saturday night amateur contest on consecutive weeks. After his second win, Tucker was hired there at full time as Master of Ceremonies, but left when it was soon discovered that he was underage. He graduated from Washington-Lee High School, Arlington, Virginia, near Washington, D.C., in 1938, and, joining the United States Cavalry, was stationed at Fort Myer in Arlington County, Virginia, but discharged for, once again, being underage. He returned to work at the Old Gaiety after his 18th birthday.