"Smooth" is a collaboration between Latin rock band Santana and Matchbox Twenty vocalist Rob Thomas. The song was written by Thomas, DeGaetano, and Itaal Shur, produced by Matt Serletic and sung by Thomas. It won three Grammy Awards: Record of the Year, Song of the Year, and Best Pop Collaboration with Vocals. Not only was it the final number-one Hot 100 hit of the 1990s, it was also the number-two Hot 100 hit of the 20th century. "Smooth" is the only song to appear on two decade-end Billboard charts. As of 2013, "Smooth" is ranked the second most successful song of all time by Billboard.