"Smooth Operator" is the lead single released from Big Daddy Kane's second album, It's a Big Daddy Thing. Arguably one of Big Daddy Kane's most popular songs, the song topped the newly formed Billboard Hot Rap Singles chart and was a hit on the R&B and dance charts, peaking at number 11 and 17 on the charts respectively. Actor and comedian Chris Rock appears in the music video getting his hair cut. He appears 2 minutes, and 23 seconds into the video.