Born in Beuthen, Upper Silesia (present-day Bytom, Poland), his family moved to Berlin after the Silesian Uprisings in 1921. He studied violin and clarinet at the Academy of Music and played in jazz and swing dance orchestras to earn a living, later becoming a bandleader. During the Nazi era, Winter adjusted to the regulations given by the "Reichsmusikkammer" and concentrated on singing and light dance music. As a Wehrmacht soldier, he was taken prisoner by American forces in late World War II.