Christopher Cross - Sailing (Live), Toronto 2026

"Sailing" hit #1 on the Billboard Pop Chart in 1980. This song's success was extraordinary - "Sailing" won Grammys for best record and best song and it propelled Christopher Cross to win best new artist at the 1981 Grammy awards. "Sailing" was the follow-up to his other smash hit, "Ride Like the Wind", which peaked at #2 on the Billboard Chart, and became one of the defining "soft rock" songs of the era and remains culturally significant as the ultimate yacht rock anthem.