Carlos Santana - Smooth (featuring Rob Thomas) a song performed by Santana and Rob Thomas of Matchbox Twenty, who sings the lead vocals. It was released on June 15, 1999, as the lead single from Santana's 1999 studio album, Supernatural. The song was an international success, reaching number one on the US Billboard Hot 100 for 12 consecutive weeks. It was the final number-one hit of the 1990s and the first number-one hit of the 2000s, and the only song to appear on two decade-end Billboard chart