In the 1950s Winter performed in several revues and variety films with stars like Marika Rökk, but also played with jazz musicians like Hans Koller and Joe Zawinul. In 1960 he performed at the Eurovision Song Contest in London. His German entry "Du hast mich so fasziniert" ("You fascinated me so much")" written by Robert Stolz finished seventh out of thirteen. In 1977 he became Kapellmeister of the highly traditional Austrian "Hoch- und Deutschmeister" military orchestra.