" Smooth " is a song performed by American rock band 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 . It was written by Itaal Shur and Thomas, who re-wrote Shur's original melody and lyrics, and produced by Matt Serletic . 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 charts. "Smooth" is ranked as the third-most-successful song ever on Billboard's Greatest of All Time Hot 100 Songs listing. In 2000, the song won a Grammy Award for Record of the Year , Song of the Year and Best Pop Collaboration with Vocals . "Smooth" also peaked at number one in Canada and charted within the top 10 in Australia, Austria, Ireland and the United Kingdom.