His first single was the little-known "When You Gonna," released as a collaboration with Lisa Carter. His first solo offering was "Never Gonna Give You Up," released in 1987 which spent five weeks at the top of the British charts and becoming the year's highest-selling single. On 12 March 1988, "Never Gonna Give You Up" also topped the U.S. singles chart and was followed by a second U.S. #1 on 18 June with his second U.S. single release, "Together Forever." In 1989 he was nominated for a Grammy Award for Best New Artist of the Year. He lost to Tracy Chapman.