Smooth

Before recording their second album, 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. In 2000, Matchbox 20 adopted the spelling “Matchbox Twenty” and released their second album, Mad Season . The album, on the strength of several successful singles, including ” Bent ” (which peaked No. 1 on the Hot 100 chart) and ” If You’re Gone “, was certified 4× platinum in the United States. The video for “Bent” made fun of singer Thomas’s increased fame from “Smooth” by showing the other band members assaulting him. The next two singles, ” Mad Season ” and ” Last Beautiful Girl ” were not as successful.