Michael Bolton and Kenny G came together for a number of noted performances during the 1990s. Bolton’s 1991 single “Missing You Now” hit No. 12 on the Billboard Hot 100 chart in 1992, and the music video (via YouTube) featured Kenny and his soprano saxophone. Another of Bolton’s songs, “How Am I Supposed To Live Without You,” let the two make an earlier splash at the 1990 Grammy Awards (also via YouTube). Professionally, the collaborations with Bolton were just one of several team-ups with notable vocalists for Kenny, who told The Washington Post in 1993 that he preferred to be led by the singer in such duets.
Personally, the two men were friends and socialized away from the stage, frequenting the same parties. It was at one such party in 1991 that Kenny unexpectedly played matchmaker when he brought another friend along, actress Nicollette Sheridan. When she met Bolton through Kenny, she told TV Guide (via Knots Landing), sparks didn’t fly immediately, and the press claimed that they were dating before they actually were. But the relationship would become among the most significant for both of them. Bolton and Sheridan dated for three years, 1992 to 1995, before amicably breaking up (per People). Nearly a decade later, they would revive their love affair and announce their engagement in 2006, though they called it off two years later.
