Before recording their second album, Rob Thomas collaborated with Itaal Shur on a song called "Smooth" for Carlos Santana's comeback album, "Supernatural". Thomas was supposed to act only as a songwriter for "Smooth", but Carlos Santana had him sing for it after hearing the song's demo. "Smooth" was the album's lead single and became a hit in 1999. Thomas won three Grammy Awards for writing and performing on "Smooth": Record of the Year, Song of the Year, and Best Popular Music Collaboration with Vocals.