Santana - Smooth ft. Rob Thomas - 1999 " Smooth " is a song performed by American rock band Santana , with Rob Thomas of Matchbox Twenty singing the lead vocals. It was released to radio on June 15, 1999, as the lead single from Santana's 1999 studio album, Supernatural , and was physically released as a single in August. 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 No. 1 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" was ranked as the second-most-successful song ever on Billboard's Hot 100 60th Anniversary listing. In 2000, the song won a Grammy Award for Record of the Year , Song of the Year and Best Pop Collaboration with Vocals at the 42nd Annual Grammy Awards . "Smooth" also peaked at No. 1 in Canada and charted within the top 10 in Australia, Austria, Ireland and the United Kingdom. #music #charttoppers #tangled