"Smooth" is a collaboration betweenLatin rockbandSantanaandMatchbox TwentyvocalistRob Thomas. The song was written by Thomas, DeGaetano, andItaal Shur, produced byMatt Serleticand sung by Thomas. It won three Grammy Awards:Record of the Year,Song of the Year, andBest 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-endBillboardcharts. As of 2013, "Smooth" is ranked the second most successful song of all time byBillboard.